original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,727,335 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[CH2:13][O:14][CH3:15].CCN(C(C)C)C(C)C>ClCCl>[CH3:13][O:14][CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6] | COC(=O)c1cccc(O)c1 | COCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 0 | 8 | In a 500 ml round-bottomed flask, under argon flush, methyl 3-hydroxybenzoate (5 g, 32.9 mmol) was dissolved in dichloromethane (100 ml) to give a white suspension. The reaction mixture was cooled at 0° C. At that temperature chloro(methyloxy)methane (2.75 ml, 36.1 mmol) and DIPEA (6.89 ml, 39.4 mmol) were added. The r... | COCOc1cccc(C(=O)OC)c1 | null | 78.8 | null |
613,685 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[CH:13]=[C:14]([C:16]([OH:18])=[O:17])[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[CH2:13][CH:14]([C:16]([OH:18])=[O:17])[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | O=C(O)c1cc2ccc(OCc3ccccc3)cc2o1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 16 | A solution of 6-(benzyloxy)benzofuran-2-carboxylic acid (3.4 g, 12.6 mmol) in aqueous NaOH (2.5N, 40 mL) is treated with 6% Na—Hg (20 g), stirred for 16 hr, allowed to stand without stirring and decanted. The supernatant is acidified with HCl and filtered. The filtercake is air-dried to afford the title product as a wh... | O=C(O)C1Cc2ccc(OCc3ccccc3)cc2O1 | null | 64 | null |
97,846 | ord_dataset-0bf72e95d80743729fdbb8b57a4bc0c6 | null | 1982-01-01T00:08:00 | true | [O:1]=[C:2]1[N:8]2[CH2:9][CH2:10][CH2:11][C@H:7]2[C:6]2=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=[CH:14][N:5]2[C:4]2[CH:20]=[CH:21][S:22][C:3]1=2.[C-]#N.[K+].C(O)C[OH:28]>>[O:1]=[C:2]1[N:8]2[CH2:9][CH2:10][CH2:11][C@H:7]2[C:6]2=[C:12]([C:15]([O:17][CH2:18][CH2:19][OH:28])=[O:16])[N:13]=[CH:14][N:5]2[C:4]2[CH... | CCOC(=O)c1ncn2c1[C@@H]1CCCN1C(=O)c1sccc1-2 | OCCO | null | [C-]#N | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 | 8 | A mixture of 3.12 g (10 mmol) of ethyl (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxylate, 80 mg of powdered potassium cyanide and 30 ml of ethyleneglycol is stirred at 100° C. overnight. After removal of the ethyleneglycol, the residue is purified by column chrom... | O=C(OCCO)c1ncn2c1[C@@H]1CCCN1C(=O)c1sccc1-2 | null | null | null |
448,842 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14]([CH2:17]C(=O)C)(=[O:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:8]1([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:15][C:14](=[O:16])[CH3:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1 | CC(=O)CC(C)=O | ICCCCCCc1ccccc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | 6-Iodo-1-phenylhexane (17.43 g, 0.061 mol), acetyl acetone (6.66 g, 0.067) and potassium carbonate (8.41 g, 0.061 mol) were dissolved in dry absolute ethanol (75 ml) and the solution was refluxed for 18 hours. After cooling to room temperature the solution was filtered and evaporated under reduced pressure to an oil. T... | CC(=O)CCCCCCCc1ccccc1 | null | 53.5 | null |
367,105 | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | null | 1997-01-01T00:06:00 | true | [CH3:1][C:2]1[NH:3][C:4]([CH3:22])=[C:5]([CH2:18][C:19]([OH:21])=[O:20])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[CH2:8][C:9]([OH:11])=[O:10].[N+]([O-])(O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:22][C:4]1[C:5]([CH2:18][C:19]([OH:21])=[O:20])=[C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7]([CH... | CC1=C(CC(=O)O)C(c2ccccc2)C(CC(=O)O)=C(C)N1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | 0.5 | 90.3 g (0.3 mol) of 1,4-dihydro-2,6-dimethyl-4-phenyl-3,5-bis(carboxymethyl)pyridine were added in portions at from 92° to 98° C. to a solution of 375 g of 98% strength nitric acid in 1580 ml of water in the course of 30 minutes. After a further 30 minutes at 95°-98° C., the mixture was cooled to +5° C. and brought to ... | Cc1nc(C)c(CC(=O)O)c(-c2ccccc2)c1CC(=O)O | null | 65.5 | null |
922,717 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=2)(=[O:14])=[O:13])[C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.[F:26][C:27]1[CH:28]=[CH:29][C:30]2[O:35][CH2:34][CH2:33][NH:32][C:31]=2[CH:36]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CCN(CC)CC>[Cl:21][C:18]1[C... | Fc1ccc2c(c1)NCCO2 | O=C(O)c1ncc(Cl)cc1NS(=O)(=O)c1ccc(Cl)c(C(F)(F)F)c1 | null | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | 6-Fluoro-3,4-dihydro-2H-benzo[1,4]oxazine 5-chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid, T3P, and Et3N were reacted according to the procedure D to provide the title compound. HPLC purification provided 4-chloro-N-[5-chloro-2-(6-fluoro-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl)-pyridin-3-yl]-3... | O=C(c1ncc(Cl)cc1NS(=O)(=O)c1ccc(Cl)c(C(F)(F)F)c1)N1CCOc2ccc(F)cc21 | null | null | null |
227,565 | ord_dataset-d98d003e9abb4b579746c5a361466e14 | null | 1991-01-01T00:05:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:20]([CH3:22])[CH3:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH:23](=[O:26])[C:24]#[CH:25]>C1COCC1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]=[C:10]([CH:20]([CH3:22])[CH3:21])[N:9]([CH:25]=[CH:24][CH:23]=[O:26])[C:... | C#CC=O | CC(C)c1nc(-c2ccc(F)cc2)c(-c2ccc(F)cc2)[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole (492 mg) in dry THF under nitrogen was added propiolaldehyde (0.97 ml) and the reaction mixture heated to reflux. Further quantities of propiolaldehyde were added in portions (3×1.1 g) during successive 2 h periods. The reaction mixture was concent... | CC(C)c1nc(-c2ccc(F)cc2)c(-c2ccc(F)cc2)n1C=CC=O | null | null | null |
215,179 | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | null | 1990-01-01T00:09:00 | true | [NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([CH2:10]Cl)=[CH:4][N:3]=1.[NH2:12][C:13]1[CH:38]=[CH:37][C:16]([C:17]([NH:19][C@H:20]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:18])=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C.[K+].[Br-]>CN(C=O)C>[... | CC(C)(C)OC(=O)CC[C@H](NC(=O)c1ccc(N)cc1)C(=O)OC(C)(C)C | N#Cc1nc(CCl)cnc1N | null | [Br-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 20 | 2-Amino-5-chloromethylpyrazine-3-carbonitrile (1.68 g, 0.01 mol) was added in small portions over 10 min to a stirred solution of di-tert-butyl N-(4-aminobenzoyl)-L-glutamate (3.78 g, 0.01 mol) and i-Pr2NEt (1.74 mL, 1.29 g, 0.01 mol) in dry DMF (25 mL). After 20 hours at room temperature, the solvent was evaporated un... | CC(C)(C)OC(=O)CC[C@H](NC(=O)c1ccc(NCc2cnc(N)c(C#N)n2)cc1)C(=O)OC(C)(C)C | null | null | null |
1,019,938 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].[H-].[Na+].[S:12]1[C:16]([C:17]2[C:22]([Br:23])=[CH:21][N:20]=[C:19](Cl)[N:18]=2)=[CH:15][C:14]2[CH:25]=[CH:26][CH:27]=[CH:28][C:13]1=2>C1COCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[S:12]1[C:16]([C:17]2[C:22]([Br:23])=[CH:21][N:20]=[C:19]([O:1][CH2:2][CH2:3][N:4]3[CH... | O=C1NCCN1CCO | Clc1ncc(Br)c(-c2cc3ccccc3s2)n1 | null | O=C([O-])O | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 8 | 1-(2-Hydroxyethyl)imidazolidin-2-one (0.6 g, 4.6 mmol) was taken up in anhydrous THF (5 mL) and added dropwise to a reaction flask containing a suspension of sodium hydride (0.147 g (60% in oil), 3.68 mmol) in anhydrous THF (10 mL) at 0° C. The ice bath was removed and the reaction allowed to warm up to room temperatur... | O=C1NCCN1CCOc1ncc(Br)c(-c2cc3ccccc3s2)n1 | null | null | null |
1,092,800 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH2:1]([C:5]1[NH:6][C:7]([CH2:11][NH:12][C:13]2[N:14]=[CH:15][NH:16][C:17]=2[C:18]([NH2:20])=[O:19])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:21]([N:29]=[C:30]=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.CO>[C:21]([NH:29][C:30]([CH:11]([NH:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18](... | O=C(N=C=S)c1ccccc1 | CCCCc1nc(Cl)c(CNc2nc[nH]c2C(N)=O)[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 25 | 4 | 4-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.30 g, 1.01 mmol, obtained from Example 7(a)) was dissolved in CH2Cl2 (5 mL) and methanol (2 mL). Benzoylisothiocyanate (0.18 g, 1.11 mmol) was added and the mixture was stirred at r.t. for 4 h. The mixture was then concentrated in vacuo ... | CCCCc1nc(Cl)c(C(Nc2nc[nH]c2C(N)=O)C(=S)NC(=O)c2ccccc2)[nH]1 | null | 37.7 | null |
144,689 | ord_dataset-d6cdba90760a47779a36ece5962905eb | null | 1986-01-01T00:06:00 | true | C(OC([NH:8][CH:9]1[CH2:15][S:14][CH2:13][CH2:12][N:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:10]1=[O:21])=O)(C)(C)C.[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25]>>[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25].[NH2:8][CH:9]1[CH2:15][S:14][CH2:13][CH2:12][N:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:10]1=[... | COC(=O)CN1CCSCC(NC(=O)OC(C)(C)C)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | 6-t-Butoxycarbonylamino-4-N-(carbomethoxymethyl)-perhydro-1,4-thiazepin-5-one (0.53 g) is dissolved in 2 ml of trifluoroacetic acid. At the end of one hour at room temperature the trifluoroacetic acid is removed under vacuum. The residue is partitioned between water and ether. The aqueous layer is washed three more tim... | COC(=O)CN1CCSCC(N)C1=O | null | null | null |
1,754,996 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](Br)[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[Cl:25])[CH:10]=2)=[O:5])[CH3:2].[C:27]([Cu])#[N:28].N#N.Cl>C(Cl)Cl.CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:27]#[N:28])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][... | N#C[Cu] | CCOC(=O)c1nc(Br)c2cc(Oc3ccc(F)cc3Cl)ccc2c1O | null | Cl | N#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | 130 | 3 | A 20-mL scintillation vial was charged with 1-bromo-4-hydroxy-7-(4-fluoro-2-chloro-phenoxy)-isoquinoline-3-carboxylic acid ethyl ester (340 mg, 0.77 mmol), CuCN (138 mg, 1.54 mmol) and NMP (1.8 mL). It was filled with N2 gas and close-capped. The mixture was stirred in a 130° C. oil bath for 3 h. Reaction mixture was d... | CCOC(=O)c1nc(C#N)c2cc(Oc3ccc(F)cc3Cl)ccc2c1O | null | 77.9 | null |
1,122,582 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([Cl:12])=[CH:4][N:3]=1.[CH2:13]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[CH:14]([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C>C(O)(C)C>[Cl:12][C:5]1[C:6]([N:20]2[CH2:21][CH2:22][N:17]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:18][CH2:19]2)=[C:7]([N+:8]([O-:10])=[O:9])... | CC(C)CN1CCNCC1 | Nc1ncc(Cl)c(Cl)c1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CC(C)O | null | null | null | null | null | null | null | null | null | 45 | null | To a mixture of 2-amino-4,5-dichloro-3-nitropyridine (0.060 g, 0.29 mmol) and isopropanol (4.5 ml) was added 1-isobutyl-piperazine (0.045 g, 0.32 mmol) with the aid of isopropanol (0.5 ml) followed by diisopropylethylamine (0.06 ml, 0.32 mmol). The reaction mixture was heated at 45° C. for 18 h, then allowed to cool to... | CC(C)CN1CCN(c2c(Cl)cnc(N)c2[N+](=O)[O-])CC1 | null | null | null |
951,483 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[N:30]=[C:29]([O:31][CH3:32])[C:28](B(O)O)=[CH:27][N:26]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[... | COc1ncc(B(O)O)c(OC)n1 | O=C(NCc1cn(-c2ccc(I)cc2)nn1)c1ccc(Cl)s1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | 125 | null | The mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (4.1, 48 mg, 0.11 mmol, synthesized by procedures similar to those that were used to make compound 1.5 described in SCHEME 1), 2,4-dimethoxypyrimidin-5-ylboronic acid (4.2, 24 mg, 0.13 mmol), PdCl2(PPh3)2 (38 mg, 0.05 mmol... | COc1ncc(-c2ccc(-n3cc(CNC(=O)c4ccc(Cl)s4)nn3)cc2)c(OC)n1 | null | null | null |
1,416,740 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH:12]=1)=O>C1COCC1>[CH2:22]([O:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH:12]=[C:11]([CH2:9][OH:8])[CH:20]=1)[C... | COC(=O)c1cc(OCc2ccccc2)c2cc(F)ccc2c1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a suspension of LiAlH4 (1.76 g, 46.4 mmol) in dry THF (20 mL) was added a solution of 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (4.80 g, 15.5 mmol) in THF (30 mL) drop wise at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quench... | OCc1cc(OCc2ccccc2)c2cc(F)ccc2c1 | null | 82.3 | null |
755,687 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21]([O:23][C:24](=O)[C:3](=[C:4]23)[CH:2]=1)=[O:22].[CH2:26]([NH2:29])[CH:27]=[CH2:28]>CN1CCCC1=O>[CH2:26]([N:29]1[C:21](=[O:22])[C:5]2[C:4]3[C:19]4[C:8](=[CH:7][CH:6]=2)[C:9]2[C:20]5[C:13]([... | O=C1OC(=O)c2ccc3c4cccc5cccc(c6ccc1c2c63)c54 | C=CCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 85 | null | A mixture of 5 g (15.5 mmol) of perylene-3,4-dicarboxylic anhydride (prepared in accordance with Liebigs Ann. 1995, 1229–1244), 11.4 g (0.2 mol) of allylamine and 1200 ml of N-methylpyrrolidone was heated at 85° C. in a 2 1 autoclave for 7 h and then cooled to room temperature, the autoclave was let down, the solvent w... | C=CCN1C(=O)c2ccc3c4cccc5cccc(c6ccc(c2c36)C1=O)c54 | null | null | null |
1,646,742 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [Cl:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.N.O1CCOCC1.CC[N:21](C(C)C)C(C)C>CCOCC>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:21])=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1 | O=C(Cl)c1cc(Cl)nc(Cl)n1 | CCN(C(C)C)C(C)C | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of 2,6-dichloropyrimidine-4-carbonyl chloride (26.13 g, 123.6 mmol) in Et2O (500 mL) was added a mixture of 0.5M ammonia in dioxane (250 mL, 125 mmol) and iPr2NEt (22 mL, 126 mmol) dropwise over approximately 50 minutes. After stirring overnight the reaction was concentrated in vacuo to a residue and chro... | NC(=O)c1cc(Cl)nc(Cl)n1 | null | 41.1 | null |
851,783 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH:22]=O)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:... | O=CC1(c2ccc(OCCCN3CCCC3)cc2)CCOCC1 | CN1CCNCC1 | null | [Ti+4] | CC(C)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (500 mg, 1.58 mmol, 1 wt), 1-methylpiperazine (300 mg, 2.99 mmol), absolute ethanol (20 ml, 40 vol), activated 3 Å molecular sieves (500 mg), titanium (IV) isopropoxide (2.32 ml, 7.83 mmol) and STAB (1.43 g, 6.73 mmol) were reacted i... | CN1CCN(CC2(c3ccc(OCCCN4CCCC4)cc3)CCOCC2)CC1 | null | 56.7 | null |
570,736 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [Sn](Cl)Cl.[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:18])=[C:9]([CH:17]=1)[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[N:19]([O-])=O.[Na+]>Cl>[Cl:18][C:8]1[CH:7]=[CH:6][C:5]([NH:4][NH2:19])=[CH:17][C:9]=1[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13] | CCOC(=O)C=Cc1cc(N)ccc1Cl | O=N[O-] | null | Cl | Cl[Sn]Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 1 | First, 60 g of tin (II) chloride was dissolved in 60 ml of concentrated hydrochloric acid, and the mixture was cooled to −30° C., to which a diazonium solution prepared from 19 g of ethyl 5-amino-2-chlorocinnamate and 6.3 g of sodium nitrite was added dropwise at 0° C. or lower. The reaction mixture was stirred at room... | CCOC(=O)C=Cc1cc(NN)ccc1Cl | null | 34.5 | null |
1,641,820 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | C(OC([N:8]1[C:12]2[CH:13]=[C:14]([Cl:19])[CH:15]=[C:16]([CH2:17]O)[C:11]=2[O:10][C:9]1=[O:20])=O)(C)(C)C.[CH2:21]([O:23][C:24](=[O:40])[CH2:25][CH:26]([N:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[NH:32][C:31]1=[O:39])[CH2:27][CH2:28][CH3:29])C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O... | CCCC(CC(=O)OCC)n1c(=O)[nH]c2ccccc21 | CC(C)(C)OC(=O)n1c(=O)oc2c(CO)cc(Cl)cc21 | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 0.25 | 5-Chloro-7-hydroxymethyl-2-oxo-benzooxazole-3-carboxylic acid tert-butyl ester 600 mg (2 mmol) is dissolved in tetrahydrofuran 1.5 mL and then 3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester is added (608 mg (2.2 mmol). The reaction is cooled to 0° C. and then triphenylphosphine (630 mg, 2.4 mmol) is... | CCCC(CC(=O)OC)n1c(=O)n(Cc2cc(Cl)cc3[nH]c(=O)oc23)c2ccccc21 | null | 3.6 | null |
855,181 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:23]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:33][C:34]1[CH:35]=[C:36]2[C:40](=[CH:41][CH:42]=1)[NH:39][CH:38]=[CH:37]2>C(O)... | CC(C)(C)OC(=O)N1CC=C(c2cc3c(Cl)ncnc3n2S(=O)(=O)c2ccccc2)CC1 | Nc1ccc2[nH]ccc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCO | null | null | null | null | null | null | null | null | null | null | 80 | 1 | 4-(7-Benzenesulfonyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (150 mg, 0.31 mmol) in butanol (5 mL) was treated with 5-aminoindole (50 mg, 0.38 mmol) and heated to 80° C. for 2 h and then 85° C. for 1 h. The mixture was evaporated to dryness and pre-absorbed o... | CC(C)(C)OC(=O)N1CC=C(c2cc3c(Nc4ccc5[nH]ccc5c4)ncnc3n2S(=O)(=O)c2ccccc2)CC1 | null | null | null |
528,081 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | Cl.C[O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[CH:10][CH:9]=1)[NH2:6].[CH3:25][C:26]1[N:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](O)=[O:29]>>[CH3:25][C:26]1[N:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([NH:6][C@H:5]([C:4]([OH:3... | Cc1ncccc1C(=O)O | COC(=O)[C@@H](N)Cc1ccc(OCc2c(Cl)cccc2Cl)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | from O-(2,6-dichlorobenzyl)-L-tyrosine methyl ester hydrochloride and 2-methylnicotinic acid. δH (DMSO-d6) 8.73 (1H, br d), 8.48 (1H, m), 7.7-7.46 (4H, m), 7.4-7.23 (3H, m), 7.00 (2H, d, J 8.4 Hz), 5.2) (2H, s), 4.60 91H, m), 3.27-3.12 (1H, m), 3.0-2.82 (1H, m); m/z (ESI, 60V) 509 (MH+). | Cc1ncccc1C(=O)N[C@@H](Cc1ccc(OCc2c(Cl)cccc2Cl)cc1)C(=O)O | null | null | null |
1,754,136 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH3:1][C:2]([CH3:18])([CH3:17])[CH:3]([NH:10]S(C(C)(C)C)=O)[C:4]1[O:5][C:6]([CH3:9])=[N:7][N:8]=1.Cl.O1CCOCC1>CO>[CH3:1][C:2]([CH3:18])([CH3:17])[CH:3]([C:4]1[O:5][C:6]([CH3:9])=[N:7][N:8]=1)[NH2:10] | Cc1nnc(C(NS(=O)C(C)(C)C)C(C)(C)C)o1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of N-[2,2-dimethyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)propyl]-2-methyl-propane-2-sulfinamide (example 174a, 462 mg, 1.69 mmol) in methanol (10 ml) was added a 4M solution of hydrochloric acid in dioxane (845 μl, 3.38 mmol). The reaction was stirred for 1 hour at room temperature. The reaction was then conce... | Cc1nnc(C(N)C(C)(C)C)o1 | null | 57.7 | null |
115,397 | ord_dataset-d182ca8cf3f34de69c7a38343db8c930 | null | 1984-01-01T00:03:00 | true | [C:1]([O:18][CH:19]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:20][C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[... | N[C@@H](Cc1ccccc1)C(=O)O | CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCCCC)CC(=O)NCC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from N-(3-hexadecanoyloxyoctadecanoyl)glycine (2.6 g) prepared by the method described in Example 27 and L-phenylalanine (1.65 g), N-[N-(3-hexadecanoyloxyoctadecanoyl)glycyl]-L-phenylalanine (2.1 g) was obtained as powders according to a similar manner to that of Example 29. | CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCCCC)CC(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)O | null | 64.8 | null |
402,226 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | C(OC([NH:8][CH:9]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][CH:9]([CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:24][... | COC(=O)C(CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1)NC(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | The compound of Example 211 (0.96 g) in TFA (10 ml) was kept at room temperature for 2 hours. The solution was evaporated and the residue dissolved in water (15 ml) and the solution basified with sodium carbonate. The mixture was extracted three times with dichloromethane. Evaporation of the combined extracts gave the ... | COC(=O)C(N)CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | 74.1 | null |
463,004 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:13]([CH2:14][CH2:15][CH3:16])[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH:9]2[O:24][CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)=[CH:4][CH:3]=1.Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:13]([CH2:14][CH2:15][CH3:16])[CH2:12][NH:11][CH... | CCCC1CN(C(=O)OC(C)(C)C)CC(OCc2ccc3ccccc3c2)C1c1ccc(Cl)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 50 | 8 | A solution of 210 mg (0.425 mmol) of tert-butyl (3RS,4RS, 5SR)-4-(4-chloro-phenyl)-3-naphthalen-2-ylmethoxy-5-propyl-piperidine-1-carboxylate in 18 ml of methanol was treated with 12 ml of 1 N hydrochloric acid and stirred at 50° C. overnight. Subsequently, the solution was evaporated under reduced pressure, the residu... | CCCC1CNCC(OCc2ccc3ccccc3c2)C1c1ccc(Cl)cc1 | null | 91.4 | null |
195,968 | ord_dataset-a58d1baeeea441fb9918c10f18f2cdb9 | null | 1989-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[O:10][C:11]3[C:18]([CH2:19][CH2:20][CH3:21])=[CH:17][C:16]([CH2:22][CH2:23][CH3:24])=[C:15]([OH:25])[C:12]=3[C:13]=2[CH3:14])=O)=[CH:5][CH:4]=1.NN.[OH-].[K+].O>C(O)CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:9]2[O:10][C:11]3[C:18]([CH2:19][CH2:20][CH3:21])=[CH:1... | CCCc1cc(CCC)c2oc(C(=O)c3ccc(OC)cc3)c(C)c2c1O | null | null | NN | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | OCCO | O | null | null | null | null | null | null | null | null | null | 195 | null | A mixture of 2 (p-methoxybenzoyl)-3 methyl-4-hydroxy-5,7-dipropylbenzofuran (0.30 gm; 0.80 mmoles), 99% hydrazine (0.2 mL), potassium hydroxide (0.40 gm; 7mmoles) in ethylene glycol (10 mL) was heated at 140° C. for a period of 2.5 hours and at 195° C. for one hour. The reaction mixture was cooled, poured into water, a... | CCCc1cc(CCC)c2oc(Cc3ccc(OC)cc3)c(C)c2c1O | null | 49.7 | null |
1,087,130 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH3:1][C@H:2]1[C@@:6]([CH2:8][CH2:9][CH3:10])([OH:7])[CH2:5][CH2:4][NH:3]1.[F:11][C:12]1[CH:19]=[C:18](F)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C(=O)([O-])[O-].[Li+].[Li+]>>[F:11][C:12]1[CH:19]=[C:18]([N:3]2[CH2:4][CH2:5][C@@:6]([OH:7])([CH2:8][CH2:9][CH3:10])[C@@H:2]2[CH3:1])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15] | CCC[C@]1(O)CCN[C@H]1C | N#Cc1ccc(F)cc1F | null | O=C([O-])[O-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By an operation in the same manner as in Example 1 and using (2S,3S)-2-methyl-3-propylpyrrolidin-3-ol 0.5 oxalate (250 mg), 2,4-difluorobenzonitrile (367 mg) and lithium carbonate (195 mg), the title compound was obtained as colorless oil (yield: 287 mg, yield: 83%). | CCC[C@]1(O)CCN(c2ccc(C#N)c(F)c2)[C@H]1C | null | null | null |
179,881 | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | null | 1988-01-01T00:11:00 | true | [CH2:1]([S:3][C@@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[NH:9][C:10](=[O:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2].OO.O.C(OCC)(=[O:25])C>CO>[CH2:1]([S:3]([C@@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[NH:9][C:10](=[O:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:25])[CH3:2] | CCS[C@@H]1NC(=O)[C@H]1NC(=O)COc1ccccc1 | CCOC(C)=O | null | OO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 0.224 g of (3R,4S)-4-ethylthio-3-phenoxyacetamido-2-oxoazetidine in 3 ml of methanol is added 0.16 ml of 30% aqueous hydrogen peroxide and the mixture is stirred at room temperature for 4 hours. Then, 0.1 ml of 30% aqueous hydrogen peroxide is added, and the mixture is further stirred for 4 hours, foll... | CCS(=O)[C@@H]1NC(=O)[C@H]1NC(=O)COc1ccccc1 | null | null | null |
1,384,637 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]1=[O:18].[F:19][C:20]1[CH:21]=[C:22]([CH2:27][C:28](O)=[O:29])[CH:23]=[C:24]([F:26])[CH:25]=1>>[F:19][C:20]1[CH:21]=[C:22]([CH2:27][C:28]([NH:1][N:2]2[N:11]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16... | O=C(O)Cc1cc(F)cc(F)c1 | Nn1nc(-c2ccccc2)c2c(c1=O)CCCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product from Example 185A and 2-(3,5-difluorophenyl)acetic acid were treated using a method similar to that described in Example 17C to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.68-11.71 (bs, 1H), 7.39-7.51 (m, 5H), 7.04-7.20 (m, 3H), 3.72 (s, 2H), 2.51-2.55 (m, 2H), 2.37-2.41 (m, 2H), 1.69-1.77 (... | O=C(Cc1cc(F)cc(F)c1)Nn1nc(-c2ccccc2)c2c(c1=O)CCCC2 | null | null | null |
1,174,702 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [CH3:1][C:2]1([C:15](=[O:28])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)[CH:18]=2)[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.Cl>CO>[CH3:1][C:2]1([C:15]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)[CH:18]=2)=[O:28])[CH2:3][CH2:4][NH:5][CH... | CC(C)(C)OC(=O)N1CCC(C)(C(=O)Nc2cccc(-c3cnco3)c2)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 15 | To a solution of tert-butyl 4-methyl-4-(3-(oxazol-5-yl)phenylcarbamoyl)piperidine-1-carboxylate from step A (77.7 mg, 0.202 mmol) in methanol (3 mL) was added HCl (4.0 N in dioxane, 0.4 mL, 1.6 mmol). The reaction was stirred for 15 hours and then concentrated to dryness to give the title compound as the hydrochloride ... | CC1(C(=O)Nc2cccc(-c3cnco3)c2)CCNCC1 | null | null | null |
843,364 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | N1[CH:5]=[CH:4][CH:3]=N1.[N:6]1([CH:11](C)[CH2:12][NH:13][C:14]([C:16]2[C:20]([Br:21])=[C:19]([NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[NH:18][N:17]=2)=[O:15])[CH2:10]CC[CH2:7]1>>[CH3:10][N:6]([CH2:11][C@H:12]([NH:13][C:14]([C:16]1[C:20]([Br:21])=[C:19]([NH:22][C:23](=[O:31])[C:24]2[CH... | CC(CNC(=O)c1n[nH]c(NC(=O)c2ccccc2Cl)c1Br)N1CCCC1 | c1cn[nH]c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The pyrazole acid, prepared as described in Procedure 8, was coupled with (R)—N,N-dimethyl-4-phenyl-1,2-butanediamine (prepared as shown in Procedure 2) using the method of Procedure 3. | CN(C)C[C@@H](CCc1ccccc1)NC(=O)c1n[nH]c(NC(=O)c2ccccc2Cl)c1Br | null | null | null |
520,319 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | B.[Br:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([N:12]([CH3:14])[CH3:13])=O)[CH:6]=[CH:7][CH:8]=1.[ClH:15]>O1CCCC1>[ClH:15].[Br:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][N:12]([CH3:13])[CH3:14])[CH:6]=[CH:7][CH:8]=1 | CN(C)C(=O)Cc1cccc(Br)c1 | null | null | B | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 90 | null | Borane in tetrahydrofuran (1.0M, 24.7 ml) was added dropwise to a tetrahydrofuran solution of 2-(3-bromophenyl)-N,N-dimethyl-acetamide (1.5 g, Example 25a)) at 0° C. Once addition was complete the solution was refluxed at 90° C. for 20 hours. The solution was cooled to room temperature, acidified with hydrochloric acid... | CN(C)CCc1cccc(Br)c1 | null | null | null |
1,320,662 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14]([N:17]([C:19]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[C:26]([OH:33])=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2)[CH3:18])(=[O:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[C... | BrCc1ccccc1 | COC(=O)c1nc(N(C)S(=O)(=O)CCCCCNC(=O)OC(C)(C)C)c2cccnc2c1O | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 8 | To a suspension of methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylate (Example 2.2; 5.44 mmol), and Cs2CO3 (10.9 mmol) in DMF (11 ml) was added benzyl bromide (10.9 mmol). The mixture was stirred overnight. The crude mixture was extracted with AcOEt/water, dried ... | COC(=O)c1nc(N(C)S(=O)(=O)CCCCCNC(=O)OC(C)(C)C)c2cccnc2c1OCc1ccccc1 | null | 75 | null |
225,671 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | [CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:20])=[C:15](F)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:20])=[C:15]([N:27]5[CH2:32][CH2:31][NH:3... | CCOC(=O)c1cn(C2CC2)c2nc3c(F)c(F)c(F)cc3cc2c1=O | C1CNCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The 1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine was prepared under the conditions of Example 35 but starting from 1.5 g of 1-cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine and 2.7 g of piperazine. After recrystalliz... | CCOC(=O)c1cn(C2CC2)c2nc3c(F)c(N4CCNCC4)c(F)cc3cc2c1=O | null | 56.4 | null |
1,321,906 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | FC1C=C(F)C=CC=1C(O[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([CH3:14])=[CH:9][C:8]=1[NH:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])=O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:16]1[O:25][C:7]2[CH:12]=[C:11]([CH3:13])[C... | Cc1cc(NC(=O)c2ccc(F)cc2F)c(OC(=O)c2ccc(F)cc2F)cc1C | null | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A suspension of 2-(2,4-difluorobenzamido)-4,5-dimethylphenyl 2,4-difluorobenzoate (90 mg, 0.22 mmol) and 4-methylbenzenesulfonic acid (82 mg, 0.43 mmol) in xylene (2 mL) was heated at reflux for 16 h. After cooling, the solution was diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution followed... | Cc1cc2nc(-c3ccc(F)cc3F)oc2cc1C | null | 63.1 | null |
1,375,819 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | C1CO[C:8]23OCC[O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([CH2:16][C@H:17]([NH:28][C:29](=[O:31])[CH3:30])[CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])O1.C([C@@H]1C2[C@](C)(CCC(=[O:52])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1)#N>>[C:29]([NH:28][C@@H:17]1[CH:18]... | CC(=O)N[C@H]1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12 | C[C@]12CCC(=O)CC1[C@@H](C#N)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound II-bd was prepared in 96% yield from 3,3:17,17-bis(ethylendioxy)-6α-acetamidoandrostane by the procedure described above for the preparation of 6α-cyanoandrostane-3,17-dione (II-ac, Prepn. 3). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. 1H-NMR (300... | CC(=O)N[C@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12 | null | 96 | null |
1,393,570 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:10][C:9]=2[C:19]2[C:20]([O:32][CH3:33])=[C:21]([NH:25]C(=O)OCC=C)[CH:22]=[CH:23][CH:24]=2)[CH:5]=[CH:4][N:3]=1.C(O)(=O)C.C([SnH](CCCC)CCCC)CCC>C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC... | C=CCOC(=O)Nc1cccc(-c2nc(N3CCOCC3)sc2-c2ccnc(Cl)n2)c1OC | null | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | CCCC[SnH](CCCC)CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of 2-propen-1-yl [3-[5-(2-chloro-4-pyrimidinyl)-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2-(methyloxy)phenyl]carbamate (40 g, 99 mmol) in DCM (500 mL), acetic acid (11.3 mL, 197 mmol) and Pd(PPh3)2Cl2 (1.3 g, 1.64 mmol) were added. Then tri-n-butyl tin hydride (37.3 mL, 145 mmol) was added dropwise to the mixt... | COc1c(N)cccc1-c1nc(N2CCOCC2)sc1-c1ccnc(Cl)n1 | null | 65.3 | null |
257,462 | ord_dataset-2369b9b9f44641b1930518c59ae89a95 | null | 1992-01-01T00:11:00 | true | Cl[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6](=[O:45])N(CCC)[C:4](=[O:49])[CH:3]=1.[CH2:50]([NH2:53])[CH2:51][CH3:52]>C(O)C>[CH2:50]([N:53]1[C:4](=[O:49])[CH:3]=[C:2]([NH:7]... | CCCN | CCCn1c(=O)cc(Cl)n(Cc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 6-chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (1.0 g) and propylamine (0.19 g) in ethanol (20 ml) was heated under reflux for 18 hours with stirring. The reaction mixture was concentrated to dryness and then the residue was extracted with methylene chlori... | CCCNc1cc(=O)n(CCC)c(=O)n1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | null | 173.2 | null |
393,239 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C)C=CC=CC=1>CC1C=CC(C)=CC=1>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:11][CH2:12][CH2:7][CH2:8][CH2:9][CH3:10] | CCCCCC | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccc(C)cc1 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | When the dispersion of the solid polymer electrolyte was added to organic solvents having a dielectric constant of less than 3, such as n-hexane, benzene, toluene, p-xylene and dodecane having dielectric constants of 1.89, 2.28, 2.38, 2.27 and 2.02, respectively, the solid polymer electrolyte produced a white precipita... | CCCCCCCCCCCC | null | null | null |
1,324,039 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [NH2:1][C:2]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C:7]2=[N:6][N:5]=1)=[S:3].[CH3:20][N:21]([CH3:24])[CH:22]=O>>[CH3:20][N:21](/[CH:24]=[N:1]/[C:2]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C:7]2=[N:6][... | CC(C)(C)OC(=O)N1CCn2c(nnc2C(N)=S)C1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of 1,1-dimethylethyl 3-(aminocarbonothioyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (I112) (99 mg, 0.349 mmol) in N,N-dimethylformamide (DMF) dimethyl acetal (3 ml, 22.41 mmol) was stirred at room temperature for 1 h. The mixture became red/orange and never went to a clear solution. The DM... | CN(C)/C=N/C(=S)c1nnc2n1CCN(C(=O)OC(C)(C)C)C2 | null | null | null |
1,702,747 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]=12)=[O:5])[CH3:2].[Cl:15][C:16]([Cl:21])([Cl:20])[C:17](Cl)=[O:18]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:17](=[O:18])[C:16]([Cl:21])([Cl:20])[Cl:15])[N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]=12)=[O:5])[CH3:2] | O=C(Cl)C(Cl)(Cl)Cl | CCOC(=O)c1ccn2c1COCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 72 | To a solution of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester (Comp. No. 2a) (8.2 g, 42 mmol) in anhydrous dichloromethane (50 ml) was added trichloro-acetyl chloride (15.2 g, 84 mmol). The resulting mixture was stirred at room temperature for 3 days, and then evaporated to dryness. The crude... | CCOC(=O)c1cc(C(=O)C(Cl)(Cl)Cl)n2c1COCC2 | null | null | null |
915,165 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:2]([C:6]([N:8]1[CH2:30][CH2:29][CH2:28][C@H:9]1[C:10]([NH:12][C@H:13]([C:17]([N:19]1[CH2:27][CH2:26][CH2:25][C@H:20]1[C:21]([CH2:23]Cl)=[O:22])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4]>[Zn]>[NH:1]([C:31... | CC(C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)N1CCC[C@H]1C(=O)CCl | null | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 15 (1.1 g, 1.91 mmol) was treated as described for 18 using acidic acid (5.3 ml) and zinc (1.31 g). | CC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(C)C | null | null | null |
1,626,772 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH:1]1([C:4]([C:6]2[CH:7]=[N:8][C:9]3[C:14]([C:15]=2[NH:16][C:17]2[CH:18]=[N:19][N:20]([C@H:22]4[CH2:27][CH2:26][C@H:25]([NH:28]C(=O)OC(C)(C)C)[CH2:24][CH2:23]4)[CH:21]=2)=[CH:13][C:12]([C:36]2[CH:41]=[C:40]([Cl:42])[C:39]([OH:43])=[C:38]([Cl:44])[CH:37]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[ClH:5... | CC(C)(C)OC(=O)N[C@H]1CC[C@H](n2cc(Nc3c(C(=O)C4CC4)cnc4ccc(-c5cc(Cl)c(O)c(Cl)c5)cc34)cn2)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of tert-butyl (trans-4-(4-((3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-yl)amino)-1H-pyrazol-1-yl)cyclohexyl)carbamate (23 mg, 0.036 mmol) in THF (3 mL) was added trifluoroacetic acid (2 mL). The resultant mixture was heated at 65° C. for 16 h. The mixture was then cooled to room t... | N[C@H]1CC[C@H](n2cc(Nc3c(C(=O)C4CC4)cnc4ccc(-c5cc(Cl)c(O)c(Cl)c5)cc34)cn2)CC1 | null | null | null |
264,827 | ord_dataset-a7bd0db0684c464bb02ff6a36065fee3 | null | 1993-01-01T00:03:00 | true | [CH2:1]([O:8][CH2:9][CH:10]1[O:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([O:8][CH2:9][CH:10]([OH:12])[CH2:11][N:17]1[C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]2[C:13]1... | O=C1NC(=O)c2ccccc21 | c1ccc(COCC2CO2)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Freshly distilled benzyl-glycidylether (60 g, 0.365 mmol), phthalimide (49.2 g, 0.304 mmol) and potassium carbonate (3.34 g, 24 mmol) were refluxed with stirring in ethanol (500 ml) for 27 hours. TLC indicated full conversion of the starting material. Ethanol was removed in vacuo. The residual oily material was transfe... | O=C1c2ccccc2C(=O)N1CC(O)COCc1ccccc1 | null | 80 | null |
1,037,457 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [C:1]([O:5][C:6]([NH:8][C:9]1([C@@H:12]2[CH2:16][CH2:15][N:14]([C@H](C3C=CC=CC=3)C)[CH2:13]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[CH2:25]([O:32][C:33]([N:14]1[CH2:15][CH2:16][C@@H:12]([C:9]2([NH:8][C:6]([O:5][C:1]([CH3:... | C[C@@H](c1ccccc1)N1CC[C@@H](C2(NC(=O)OC(C)(C)C)CC2)C1 | O=C(Cl)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | 3-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidine (1.70 g, 5.15 mmol) was dissolved in dichloromethane (34 ml), and benzylchloroformate (1.10 ml, 7.73 mmol) was added dropwise while stirring and cooling with ice. The reaction solution was then stirred at room temperature for 2.5 hours and... | CC(C)(C)OC(=O)NC1([C@@H]2CCN(C(=O)OCc3ccccc3)C2)CC1 | null | 75.4 | null |
1,169,032 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C1COCC1.C[O:7][C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:11][CH:10]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][OH:7])=[CH:10][CH:11]=1 | COC(=O)c1ccc(OCc2ccccn2)cc1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.33 | To a solution of THF (50 mL) of 4-(pyridin-2-ylmethoxy)-benzoic acid methyl ester (4.9 g) described in Manufacturing Example 25-1 was added LAH (1.0 g) at 0° C., which was stirred for 20 minutes at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was ... | OCc1ccc(OCc2ccccn2)cc1 | null | 36.9 | null |
1,104,577 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[C:15]([OH:16])=[C:14]([C:17](=O)[CH3:18])[C:13]([CH3:20])=[N:12]1.[CH3:21][O:22][C:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=[O:30])=[CH:27][CH:26]=1)=[O:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=... | CC(=O)c1c(C)nn(-c2ccc3ccccc3n2)c1O | COC(=O)c1ccc(C(=O)NN)cc1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | O | null | null | null | null | null | null | null | null | null | null | null | 2.0 mL of an isopropyl alcohol solution of 28.7 mg (0.11 mmol) of 1-(1-(quinolin-2-yl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)-ethanone, 20.8 mg (0.11 mmol) of 4-methoxycarbonylbenzhydrazide and 6.1 mg (0.03 mmol) of p-toluenesulfonic acid monohydrate was refluxed with heating for 48 hours. After cooling, the precipitate w... | COC(=O)c1ccc(C(=O)NNC(C)=C2C(=O)N(c3ccc4ccccc4n3)N=C2C)cc1 | null | 30.5 | null |
530,945 | ord_dataset-7774db17e619477ea20ee621abe71257 | null | 2002-01-01T00:01:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[N:10][OH:11])[CH2:2]1.[H-].[Na+].S(OC)(O[CH3:18])(=O)=O.O>CN(C)C=O>[CH3:18][O:11][N:10]=[C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][CH2:2]1 | ON=C1COc2ccccc21 | COS(=O)(=O)OC | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | null | 3.7 g of benzofuran-3-one oxime are dissolved in 15 ml of dimethylformamide. At 20° C., 1 g of sodium hydride (60%) is added and the mixture is stirred until the evolution of gas ceases. 3.15 g of dimethyl sulphate are then added dropwise and the mixture is stirred at 20° C. for 24 hours. The reaction mixture is poured... | CON=C1COc2ccccc21 | null | 42 | null |
1,087,422 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:34])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH:17]=[C:16]4[C:31](O)=[O:32])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[NH2:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])(... | Cc1ccc(C(=O)NC2CC2)cc1-c1ccc2c(=O)n(Cc3ccncc3)cc(C(=O)O)c2c1 | CC(C)(C)OC(=O)N1CCC(N)CC1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 3 | To a mixture of the product of Example 54 step iii) (0.1 g), 4-amino-N-boc-piperadine (0.05 g) and N,N-diisopropylethylamine (0.25 mL) in tetrahydrofuran (10 mL) was added HATU (0.16 g) and the mixture stirred at room temperature for 3 hours. The reaction mixture was then concentrated to dryness and the crude product p... | Cc1ccc(C(=O)NC2CC2)cc1-c1ccc2c(=O)n(Cc3ccncc3)cc(C(=O)NC3CCN(C(=O)OC(C)(C)C)CC3)c2c1 | null | null | null |
1,428,504 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [C:1]1([C:7]2[CH:12]=[C:11]([C:13]3([CH3:18])[O:17][CH2:16][CH2:15][O:14]3)[CH:10]=[CH:9][C:8]=2[NH:19][C:20]([C:22]2[N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH2:37](O)CCO.CC1C=CC(S(O)(=O)=O)=CC=1>>[C:1]1... | OCCCO | CC1(c2ccc(NC(=O)c3nc(C#N)cn3COCC[Si](C)(C)C)c(C3=CCCCC3)c2)OCCO1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-acetyl-2-cyclohex-1-enyl-phenyl)-amide (as prepared in Example 1, step (h), 0.58 mmol), 1,3-propanediol (882 mg, 11.6 mmol) and catalytic PTSA according to the procedure in Example 1, step (h) (147 mg, 49%... | CC1(c2ccc(NC(=O)c3nc(C#N)cn3COCC[Si](C)(C)C)c(C3=CCCCC3)c2)OCCCO1 | null | null | null |
478,613 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | C([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:20][CH:19]3[N:21]([CH3:22])[CH:16]([CH2:17][CH2:18]3)[CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:22][N:21]1[CH:19]2[CH2:18][CH2:17][CH:16]1[CH2:15][CH:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH2:20]2 | CN1C2CCC1CC(N1CCN(Cc3ccccc3)CC1)C2 | null | null | [Pd+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-benzyl-4-(N-methyl-8-azabicyclo[3,2,1]oct-3-yl)-piperazine (4.75 g, 15.88 mmol) in 50 ml methanol was hydrogenated at a pressure of 2.0 atm in the presence of 20% palladium hydroxide on carbon (470 mg) for 30 h. The mixture was then filtered through a pad of celite. The filtrate was concentrated to affo... | CN1C2CCC1CC(N1CCNCC1)C2 | null | null | null |
1,662,746 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | C[O:2][C:3](=O)[C:4]([I:8])=[CH:5]OC.[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH2:19].C[O-].[Na+]>C(O)C>[I:8][C:4]1[C:3](=[O:2])[N:19]=[C:11]2[NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]2[CH:5]=1 | Nc1nc2ccccc2[nH]1 | COC=C(I)C(=O)OC | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a mixture of 2-iodo-3-methoxy-acrylic acid methyl ester (1, 1.21 g, 5 mmol), 1H-benzoimidazol-2-ylamine (2, 0.67 g, 5 mmol) and ethanol (30 mL) was added a solution of sodium methoxide (10 mL, 0.5 M in methanol, 5 mmol). The resulted mixture was refluxed for 3 h and concentrated to afford 3-iodo-10H-benzo[4,5]imidaz... | O=c1nc2[nH]c3ccccc3n2cc1I | null | null | null |
269,412 | ord_dataset-a20aed058d7b40bc81fdf50bc5b03f97 | null | 1993-01-01T00:06:00 | true | C(Cl)(=O)[C:2](Cl)=[O:3].[NH2:7][C:8]1[N:13]=[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[N:22]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:21]([CH3:35])([CH3:34])[CH2:20]2)[N:11]=[C:10]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]2[CH2:46][C:45]([CH3:48])([C... | O=C(Cl)C(=O)Cl | CC1(C)CC(CCCCNc2nc(N)nc(NCCCCC3CC(C)(C)N(OC4CCCCC4)C(C)(C)C3)n2)CC(C)(C)N1OC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from the reaction of oxalyl chloride with the compound prepared in Example 22. | CC1(C)CC(CCCCNc2nc(N=C=O)nc(NCCCCC3CC(C)(C)N(OC4CCCCC4)C(C)(C)C3)n2)CC(C)(C)N1OC1CCCCC1 | null | null | null |
1,658,760 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=[N:8][OH:9])[NH2:7])#[N:2].[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=O)=[CH:16][N:15]=1>N1C=CC=CC=1>[F:13][C:14]1[N:15]=[CH:16][C:17]([C:18]2[O:9][N:8]=[C:6]([C:5]3[CH:4]=[C:3]([CH:12]=[CH:11][CH:10]=3)[C:1]#[N:2])[N:7]=2)=[CH:21][CH:22]=1 | O=C(Cl)c1ccc(F)nc1 | N#Cc1cccc(C(N)=NO)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | 3-Cyano-N′-hydroxybenzimidamide (0.322 g, 1 mmol) was dissolved in pyridine 10 mL and 6-fluoronicotinoyl chloride (Frontier Scientific, 0.160 g, 1 mmol) was added. The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The cooled reaction mixture was quenched with water (25 mL) and f... | N#Cc1cccc(-c2noc(-c3ccc(F)nc3)n2)c1 | null | null | null |
717,184 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [OH-].[K+].[CH2:3]([O:5][C:6](=[O:35])[CH:7]([CH:13]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:35])[CH:7]([CH:13]([C:21]1[CH:22]=[N... | CCOC(=O)C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCO | null | null | null | null | null | null | null | null | null | 25 | 48 | A solution of KOH (0.067 g, 1.03 mmol) in ethanol (3 mL) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-phenyl-ethyl]-malonic acid diethyl ester (0.44g, 0.96 mmol) in ethanol (3 mL) and methylene chloride (2 mL) at 0° C. The mixture was stirred for 48 h at room temperature. The mixture was ... | CCOC(=O)C(C(=O)O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | 90 | null |
1,618,262 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:12][C:13]1([F:28])[CH2:18][CH2:17][C:16]([CH2:26][NH2:27])([C:19]2[CH:20]=[N:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH2:15][CH2:14]1>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([NH:27][CH2:26][C:16]1([C:19]2[CH:20]=[N:21][C:22]([F:... | NCC1(c2ccc(F)nc2)CCC(F)(F)CC1 | Cc1ccc(Cl)c(C(=O)O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | From 2-chloro-5-methylbenzoic acid and C-[4,4-difluoro-1-(6-fluoro-pyridin-3-yl)-cyclohexyl]-methylamine. LCMS (MH+): m/z=397.2, tR (minutes, Method C)=1.11 | Cc1ccc(Cl)c(C(=O)NCC2(c3ccc(F)nc3)CCC(F)(F)CC2)c1 | null | null | null |
1,228,462 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | CC(C)([O-])C.[Na+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:33])[CH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1.[CH3:34][O:35][C:36](=[O:45])[C:37]1[CH:42]=[CH:41][C:40]([CH2:43]Br)=[CH:39][CH:38]=1>C1COCC1>[F:7][... | COC(=O)c1ccc(CBr)cc1 | O=C(Cc1cccc(-c2ccc(OC(F)(F)F)cc2)c1)c1ccccc1F | null | CC(C)(C)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | null | Sodium t-butoxide (67 mg, 0.70 mmol) was added all at once to a THF solution (4 mL) containing the intermediate from Step B (250 mg, 0.668 mmol) stirred at −78° C. After 2 minutes 4-bromomethyl-benzoic acid methyl ester (161 mg, 0.70 mmol) was added all at once. The reaction solution was allowed to warm to room tempera... | COC(=O)c1ccc(CC(C(=O)c2ccccc2F)c2cccc(-c3ccc(OC(F)(F)F)cc3)c2)cc1 | null | null | null |
1,549,523 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH3:1][N:2]([S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8]2.[Cl:23][CH2:24][C:25](=O)[CH2:26]Cl.CN(C)C(=O)C>O>[Cl:23][CH2:24][C:25]1[N:13]=[C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:... | O=C(CCl)CCl | CN(c1cccc2cc(C(N)=S)[nH]c12)S(=O)(=O)c1cccs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | 80 | 2 | A mixture of 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.46 g), 1,3-dichloro-2-propanone (0.33 g) and N,N-dimethylacetamide (6 mL) was stirred at 80° C. for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with satur... | CN(c1cccc2cc(-c3nc(CCl)cs3)[nH]c12)S(=O)(=O)c1cccs1 | null | 81.1 | null |
1,196,790 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[N:8]1[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[NH:9]1.Br[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[N:8]1[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[N:9]1[C:24]1[C:25]2[C:20](=[CH:... | CC1(C)NN(C2CC3CCC2C3)C1=O | Brc1cccc2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-(Bicyclo[2.2.1]heptan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one and 1-bromonaphtalene were used for a similar reaction and treatment as Example 181, and the title compound was obtained as a pale yellow crystalline powder. | CC1(C)C(=O)N(C2CC3CCC2C3)N1c1cccc2ccccc12 | null | null | null |
889,424 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[C:10]1[C:11](=[CH:16][C:17]([F:24])=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[C:12](OC)=[O:13]>C1COCC1>[F:24][C:17]1[C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][C:10]([CH2:9][OH:8])=[C:11]([CH2:12][OH:13])[CH:16]=1 | COC(=O)c1cc(F)c(C(F)(F)F)cc1C(=O)OC | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To 23.6 mmol LiAlH4 in 10 ml THF was added dropwise over 5 min a solution of 3.93 mmol 4-fluoro-5-trifluoromethyl-phthalic acid dimethyl ester in 5 ml THF. The mixture was stirred at room temperature for 2 h, and then heated at 50° C. for 20 min. The reaction mixture was quenched by dropwise addition of 8 ml ethyl acet... | OCc1cc(F)c(C(F)(F)F)cc1CO | null | 57 | null |
553,911 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | [OH:1][CH2:2][C:3]#[C:4][CH2:5]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[OH:1][CH2:2][C:3]#[C:4][CH2:5][N:30]1[C:26](=[O:36])[C:27]2=[CH:35][CH:34]=[CH:33][CH:32]=[C:28]2[C:29]1=[O:31] | OCC#CCO | O=C1NC(=O)c2ccccc21 | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 1,4-Dihydroxy-2-butyne (430 mg, 5.0 mmol), triphenylphosphine (1.44 g, 5.5 mmol) and phthalimide (1.47 g, 10.0 mmol) were dissolved in 50 mL of dry THF. To this solution, with stirring under dry argon, was added diisopropyl azodicarboxylate (1.09 mL, 5.25 mmol) dropwise. After stirring at room temperature for 6 hours, ... | O=C1c2ccccc2C(=O)N1CC#CCO | null | 53 | null |
186,766 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9]C(OC)=O)=[CH:4][C:3]=1[N:14]1[C:18](=[O:19])[C:17](=[C:20]([CH3:22])[CH3:21])[O:16][C:15]1=[O:23].C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:14]1[C:18](=[O:19])[C:17](=[C:20]([CH3:21])[CH3:22])[O:16][C:15]1=[O:23] | COC(=O)Oc1cc(N2C(=O)OC(=C(C)C)C2=O)c(F)cc1Cl | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | To a dried methanol solution (100 ml) of 3-(2'-fluoro-4'-chloro-5'-methoxycarbonyloxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione (3.44 g, 10 mmol), which was synthesized by a method shown in Reference Example 12 described below, was added potassium carbonate (1.38 g, 10 mmol) and the mixture was heated at reflux... | CC(C)=C1OC(=O)N(c2cc(O)c(Cl)cc2F)C1=O | null | 56 | null |
1,304,729 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]([O:12][C:13]([CH3:15])=[CH2:14])=[O:11].C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:11])[O:12][C:13]([CH3:15])=[CH2:14])[CH:6]=[CH:7][CH:8]=1 | C=C(C)OC(=O)Cl | Nc1cccc(F)c1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 8 | To a biphasic solution of 3-fluoroaniline (0.3 mL, 3.12 mmol) in 1:1 EtOAc/water (10 mL) was added isopropenyl chloroformate (0.564 g, 4.68 mmol) and NaHCO3 (1.31 g, 15.6 mmol) and the mixture stirred at RT overnight. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers ... | C=C(C)OC(=O)Nc1cccc(F)c1 | null | 20.5 | null |
1,182,926 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][C:11]([C@@H:13]1[CH2:18][CH2:17][C@H:16]([NH:19]C(=O)OC(C)(C)C)[CH2:15][CH2:14]1)=[O:12].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:19][C@@H:16]1[CH2:15][CH2:14][C@H:13]([C:11]([NH:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:1])([F:27])[F:... | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](C(=O)NCc2ccccc2C(F)(F)F)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 0 | 0.17 | To a solution of 1,1-dimethylethyl {cis-4-[({[2-(trifluoromethyl)phenyl]methyl}amino)carbonyl]cyclohexyl}carbamate in CH2Cl2 (40 ml) at 0° C., a premixed solution of CH2Cl2 (10 ml) and TFA (10 ml) was added. The reaction mixture was stirred at 0° C. for 10 min. The reaction was warmed to room temperature and stirring w... | N[C@H]1CC[C@@H](C(=O)NCc2ccccc2C(F)(F)F)CC1 | null | null | null |
589,832 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | C(OC(=O)[NH:7][C:8]1[C:13]([NH:14][C:15](=[O:30])[CH2:16][C:17](=O)[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N:24]3[CH:28]=[CH:27][N:26]=[N:25]3)[CH:19]=2)=[CH:12][C:11]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])=[C:10]([O:38][CH2:39][C:40]([F:43])([F:42])[F:41])[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:37][C:... | CC(C)(C)OC(=O)Nc1cc(OCC(F)(F)F)c(-c2ccccc2F)cc1NC(=O)CC(=O)c1cccc(-n2ccnn2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from [2′-fluoro-5-[3-oxo-3-(3-[1,2,3]triazol-1-yl-phenyl)-propionylamino]-2-(2,2,2-trifluoro-ethoxy)-biphenyl-4-yl]-carbamic acid tert.-butyl ester (Example M24) by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as an orange solid (45 mg). | O=C1CC(c2cccc(-n3ccnn3)c2)=Nc2cc(OCC(F)(F)F)c(-c3ccccc3F)cc2N1 | null | null | null |
505,311 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:20])[C:10]3[C:15]([C:16]=2[C:17]([OH:19])=O)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:35])[CH2:25][CH2:26][CH2:27][NH:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1>CN(C)C=O>[Cl:1][C:2]1[C... | Cn1c(COc2ccc(Cl)cc2)c(C(=O)O)c2ccccc21 | CN(C)CCCNCCCN(C)C | null | CCN=C=NCCCN(C)C | Cl | Oc1cccc2[nH]nnc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Under an argon atmosphere 2-[(4-chlorophenoxy)methyl]-1-methyl-3-carboxy-1H-indole (0.100 g, 0.317 mmol) was dissolved in 3.2 ml of N,N-dimethylformamide. To this solution were added N,N-bis(3-dimethylaminopropyl)amine (0.074 ml, 0.0623 g, 0.332 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.091 ... | CN(C)CCCN(CCCN(C)C)C(=O)c1c(COc2ccc(Cl)cc2)n(C)c2ccccc12 | null | null | null |
1,067,980 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.O.Cl[C:11]([CH3:15])([CH3:14])[C:12]#[CH:13]>[Cu].[Cu]Cl.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:11]([CH3:15])([C:12]#[CH:13])[CH3:14])=[CH:4][CH:3]=1 | Nc1ccc(Br)cc1 | C#CC(C)(C)Cl | null | Cl[Cu] | [Cu] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | O | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of 4-bromobenzenamine (4.0 g, 23 mmol), TEA (4.3 ml, 31 mmol), 2.0 ml of water, copper (0.058 g, 0.91 mmol) and copper(I) chloride (0.058 g, 0.59 mmol) in diethyl ether (9.8 ml, 20 mmol) was added 3-chloro-3-methylbut-1-yne (2.0 g, 20 mmol), dropwise. After stirring overnight, the reaction mixture was tra... | C#CC(C)(C)Nc1ccc(Br)cc1 | null | null | null |
495,498 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [C:1]([NH:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.Br[CH2:19][CH2:20][CH2:21][Cl:22]>O1CCCC1>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:19][CH2:20][CH2:21][Cl:22])[CH2:7][CH2:6]1)(=[O:3])[CH3:2] | ClCCCBr | CC(=O)NC1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4-acetamidopiperidine (1.4 g; preparation 14), triethylamine (3.56 ml) and 1-bromo-3-chloropropane (1.45 ml) in 50 ml of tetrahydrofuran was refluxed overnight, then an additional 3.5 ml of triethylamine and 1.45 ml of 1-bromo-3-chloropropane were added. After a further 3 hours at reflux, the mixture was c... | CC(=O)NC1CCN(CCCCl)CC1 | null | null | null |
1,275,258 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Br[C:2]1[CH:3]=[C:4]([NH:14][C:15]([C:17]2[CH:18]=[N:19][CH:20]=[N:21][CH:22]=2)=[O:16])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][C:25]=1[F:33]>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:3]=[C:4]([NH:14][C:15]([C:17]3[CH:18]=[N:19][CH:20]=[N:21][C... | O=C(Nc1cnc(OCC(F)(F)F)c(Br)c1)c1cncnc1 | OB(O)c1ccc(Cl)c(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized in analogy to Example 39, using pyrimidine-5-carboxylic acid[5-bromo-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-amide (example 52 a) and B-(4-chloro-3-fluorophenyl)-boronic acid (CAN 137504-86-0) as starting materials; LC-MS (UV peak area/ESI) 97.7%, 425.0448 (M−H)−. | O=C(Nc1cnc(OCC(F)(F)F)c(-c2ccc(Cl)c(F)c2)c1)c1cncnc1 | null | null | null |
936,108 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[N:17]=2)=O)=[CH:5][CH:4]=1)#[N:2].O>O1CCCC1>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[N:17]=[C:13]([NH:12][CH2:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH... | COc1ccc(-c2csc(NC(=O)Cc3ccc(C#N)cc3)n2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 2 | 610 mg 2-(4-Cyano-phenyl)-N-[4-(4-methoxy-phenyl)-thiazol-2-yl]-acetamide were suspended in 20 ml tetrahydrofuran. 2.1 ml of a one molar solution of borane tetrahydrofuran complex were added at room temperature. The reaction mixture was stirred at room temperature for two hours and then at 50° C. for two hours. The coo... | COc1ccc(-c2csc(NCCc3ccc(C#N)cc3)n2)cc1 | null | 102.5 | null |
1,092,587 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]([NH:16][C@H:17]1[CH2:21][CH2:20][NH:19][C:18]1=[O:22])=[O:15])[N:10]([CH2:23][CH:24]([CH3:26])[CH3:25])[N:9]=[CH:8]2.N[C@H:33]1CCCNC1=O>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O... | N[C@H]1CCCNC1=O | CC(C)Cn1ncc2cc(Oc3ccc(F)cc3F)c(C(=O)N[C@H]3CCNC3=O)cc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 2,5-dioxopyrrolidin-1-yl-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylate (prepared according to Example 16; 1.01 g, 2.28 mmol) in dichloromethane (10 mL) was added (S)-3-aminopiperidin-2-one (prepared according to Example 3; 521 mg, 4.56 mmol) and the reaction was allowed to stir overnight... | CC(C)Cn1ncc2cc(Oc3ccc(F)cc3F)c(C(=O)N[C@H]3CCCNC3=O)cc21 | null | 99.1 | null |
832,519 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:13](=[O:23])[NH:14][CH:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH:16]1[OH:22])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[CH3:30][C:31]1[N:36]=[C:35]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=[CH:33][CH:32]=1.CO>ClCCl.Cl>[C:1]([O:5][C:6](=[O:24])... | Cc1cccc(S(=O)(=O)Cl)n1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CCCNCC1O | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | null | null | To a solution of [(S)-1-(3-hydroxy-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester of Example 2 (1.0 g) in dichloromethane (20 mL) was added saturated sodium bicarbonate (50 mL). To this solution was added 6-methyl-pyridine-2-sulphonyl chloride (6.44 mL of a 0.13 g/mL solution in 9M HCl). The react... | Cc1cccc(S(=O)(=O)N2CCCC(NC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)C(O)C2)n1 | null | null | null |
1,206,859 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | Br[C:2]1[C:3]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]2[CH2:10][CH2:9][O:8][C:5]2=[N:6][CH:7]=1.[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17]>CN(C)C=O.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:17]([C:2]1[C:3]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]2[CH2:10... | C=CC[Sn](CCCC)(CCCC)CCCC | C[Si](C)(C)c1c(Br)cnc2c1CCO2 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 100 | 1.5 | A mixture of 5-bromo-4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine (37.5 g, 138 mmol), allyltributyltin (65.8 mL, 212 mmol) and trans-dichlorobis(triphenylphosphine)palladium(II) (9.9 g, 14.1 mmol) in N,N-dimethylformamide (500 mL) was stirred at 100° C. for 1.5 hr. The reaction solution was diluted with water, and... | C=CCc1cnc2c(c1[Si](C)(C)C)CCO2 | null | 95.9 | null |
228,911 | ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac | null | 1991-01-01T00:06:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]([NH:13][CH:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[N:17]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:16]([CH3:32])([CH3:31])[CH2:15]1)=[O:12])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:39](Br)[CH3:40]>>[CH2:39]([O:1][C:2]1[CH:7]=[C... | CCCCCCCCON1C(C)(C)CC(NC(=O)C(=O)Nc2ccccc2O)CC1(C)C | CCBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The above-named compound is prepared by reacting the compound prepared in Example 13A with potassium carbonate and ethyl bromide. | CCCCCCCCON1C(C)(C)CC(NC(=O)C(=O)Nc2ccccc2OCC)CC1(C)C | null | null | null |
285,710 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][CH:9]([C:25]1[N:26]=[CH:27][N:28]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]=1[CH3:30])[CH:10]1[C:23](=[O:24])[N:14]2[C:15]3[C:20]([C:21]([CH3:22])=[C:13]2[CH2:12][CH2:11... | Cc1c2n(c3ccccc13)C(=O)C(C(O)c1ncn(C(c3ccccc3)(c3ccccc3)c3ccccc3)c1C)CC2 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 20 | Acetic anhydride (5 ml) was added to a solution of 8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one (4 g, a mixture of the isomers A and B) in pyridine (50 ml). After being stirred at room temperature for 20 hours, the solution was evaporated in vacuo. Silica gel... | CC(=O)OC(c1ncn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c1C)C1CCc2c(C)c3ccccc3n2C1=O | null | null | null |
542,794 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[CH2:6]2.[C:12]([C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)([CH3:15])([CH3:14])[CH3:13]>CCOCC>[C:12]([C:16]1[CH:17]=[C:18]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([CH3:11])[CH2:6]3)[CH:19]=[C:20]([... | CC(C)(C)c1cc([Mg]Br)cc(C(C)(C)C)c1 | CC1=Cc2c(Cl)cccc2C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 4-Chloro-2-methylindene (6.1 g, 37 mmol) and NiCl]2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-Di-t-butylphenylmagnesium bromide (10 g, 37 mmol) as a Et2O solution was added to the solution and the reaction was stirred overnight at room temperature. After overnight stirring, the reaction was slowly ... | CC1=Cc2c(cccc2-c2cc(C(C)(C)C)cc(C(C)(C)C)c2)C1 | null | null | null |
1,160,620 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[CH2:11][C@@H:10]([C:27](=[O:47])[N:28]([CH:44]2[CH2:46][CH2:45]2)[CH2:29][C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[CH:3... | O=C1c2ccccc2C(=O)N1CCO | COCCCn1cc(CN(C(=O)[C@@H]2C[C@H](NS(=O)(=O)c3ccccc3[N+](=O)[O-])CN(C(=O)OC(C)(C)C)C2)C2CC2)c2ccccc21 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 60 | 13 | To a solution of (3R*,5S*)3-{Cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-5-(2-nitro-benzenesulfonylamino)-piperidine-1-carboxylic acid tert-butyl ester (400 mg, 0.60 mmol), 2-(2-hydroxyethyl) isoindole-1,3-dione (171 mg, 0.9 mmol), and PPh3 (315 mg, 1.2 mmol) in THF is added DEAD (208 mg, 1.2 mmol... | COCCCn1cc(CN(C(=O)[C@@H]2C[C@H](N(CCN3C(=O)c4ccccc4C3=O)S(=O)(=O)c3ccccc3[N+](=O)[O-])CN(C(=O)OC(C)(C)C)C2)C2CC2)c2ccccc21 | null | null | null |
496,937 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [OH:1][CH:2]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=1)[CH:3]([C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH2:14][O:15][C:9]=2[CH:8]=1)[C:4]([OH:6])=[O:5]>[OH-].[Na+].CO>[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1)[CH:3]([C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH2:14... | COC(=O)c1ccc(C(O)C(C(=O)O)c2ccc3c(c2)OCO3)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of (2RS,3SR)-3-hydroxy-2-(3,4-methylenedioxy-phenyl)-3-(4-methoxycarbonylphenyl)propionic acid (80 mg) in 1N aqueous sodium hydroxide solution (1.2 ml) and methanol (5 ml) was stirred at ambient temperature for 18 hours. The reaction was quenched with iN-hydrochloric acid and then the resulting mixture was d... | O=C(O)c1ccc(C(O)C(C(=O)O)c2ccc3c(c2)OCO3)cc1 | null | 78.2 | null |
1,049,914 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[NH4+].[Cl-]>[Zn].C1C=CC=CC=1>[CH3:14][S:13][C:4]1[N:3]=[CH:2][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1 | CCOC(=O)c1cnc(SC)nc1Cl | null | null | [Cl-] | [NH4+] | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 80 | null | Ethyl 4-chloro-2-methylthio-5-pyrimidine carboxylate (12.5 g, 53.88 mmol) and Zn powder (14.1 g, 215.52 mmol) were combined and benzene (60 ml) and 3M NH4Cl (140 ml) were added. The suspension was stirred vigorously and heated to 80° C. for 30 h. The reaction mixture was filtered through celite and washed with EtOAc (2... | CCOC(=O)c1cnc(SC)nc1 | null | null | null |
981,657 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:28]3[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]3)[N:9]=[C:10]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[CH:15]=[CH:14]4)[C:3]=12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:27][C:22]1[CH:23]=[CH:24][CH:2... | CC(C)(C)OC(=O)N1CCC(n2nc(-c3ccc4c(ccn4Cc4ccccc4Cl)c3)c3c(N)ncnc32)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of EXAMPLE 201B (1.28 g, 2.3 mmol) in anhydrous CH2Cl2 (30 ml) was cooled in an ice bath and TFA (7.5 ml) was added dropwise under inert atmosphere. After stirring 15 min the ice bath was removed and the reaction allowed to warm to ambient temperature while stirring 1 hr. The reaction was concentrated and th... | Nc1ncnc2c1c(-c1ccc3c(ccn3Cc3ccccc3Cl)c1)nn2C1CCNCC1 | null | 70 | null |
382,540 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.[CH:13]1[CH:14]=[CH:15][C:16]([C@H:19]2O[C@@H:20]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][CH:18]=1.B(F)(F)F.CCOCC>O1CCOCC1>[C:16]1([C:19]([C:3]2[C:4](=[O:12])[O:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)=... | O=c1cc(O)c2ccccc2o1 | c1ccc([C@H]2O[C@@H]2c2ccccc2)cc1 | null | FB(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 8 | To a flame-dried flask containing a mixture of 650 mg of 4-hydroxycoumarin and 1.0 g of commercially available trans-stilbene oxide in 20 mL of dioxane under an argon atmosphere is added 2.5 mL of boron trifluoride etherate. The resulting yellow solution is left to stir at room temperature overnight. The volatiles are ... | O=c1oc2ccccc2c(O)c1C(=Cc1ccccc1)c1ccccc1 | null | null | null |
1,193,463 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [F:1][C:2]([F:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][O:4][CH2:5][CH2:6][CH:7]=[O:8].[C:16]1(CCCCOCCC(O)CCC=C)[CH:21]=CC=[CH:18][CH:17]=1>>[F:1][C:2]([F:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][O:4][CH2:5][CH2:6][CH:7]([OH:8])[CH2:18][CH2:17][CH:16]=[CH2:21] | O=CCCOCC(F)(F)c1ccccc1 | C=CCCC(O)CCOCCCCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Obtained from Intermediate 82 (1.86 g, 8.7 mmol) by the procedure described in Intermediate 14. Purification by column chromatography with silica gel eluting with ethyl acetate/n-hexane (1:6) gave the title compound (1.24 g, 53%) as oil. | C=CCCC(O)CCOCC(F)(F)c1ccccc1 | null | 53 | null |
564,946 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | Cl[CH2:2][O:3][C:4](=[O:45])[CH2:5][CH:6]([CH2:26][O:27][C:28](=[O:44])[C@H:29]([CH:41]([CH3:43])[CH3:42])[NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:7][O:8][C:9](=[O:25])[C@H:10]([CH:22]([CH3:24])[CH3:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCCl | [I-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | 3,3-bis(N-CBz-L-valyloxymethyl)-propionic acid chloromethyl ester (900 mg, 1.38 mmole) was dissolved in acetonitrile (5 ml). Sodium iodide (289 mg, 1.93 mmole) was added to the solution. After reaction at 70° C. for 3 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (5 ml) and r... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCI | null | null | null |
1,346,939 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [N:1]([CH2:4][CH2:5][C@@H:6]1[CH2:8][C@@H:7]1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Cl:21][C:18]1[CH:17]=[N:16][C:15]([N:12]2[CH2:13][CH2:14][CH:9]([C@H:7]3[CH2:8][C@H:6]3[CH2:5][CH2:4][NH2:1])[CH2... | [N-]=[N+]=NCC[C@@H]1C[C@@H]1C1CCN(c2ncc(Cl)cn2)CC1 | null | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 1 | 2-{4-[(1S,2S)-2-(2-azidoethyl)cyclopropyl]piperidin-1-yl}-5-chloropyrimidine (34 mg, 0.11 mmol) from step 2 of this example was dissolved in THF (1 mL), triphenylphosphine (58.1 mg, 0.22 mmol) was added, then water (0.085 mL). The reaction was run at room temperature for 1 hour, then 40° C. 1 hour. The reaction was coo... | NCC[C@@H]1C[C@@H]1C1CCN(c2ncc(Cl)cn2)CC1 | null | null | null |
792,561 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[Cl:11].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:6][C:5]=1[Cl:11] | C1COCCN1 | COC(=O)c1ccc(F)cc1Cl | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 120 | 5 | A mixture of 2-chloro-4-fluoro-benzoic acid methyl ester (3.51 g, 18.6 mmol), morpholine (1.95 mL, 22.3 mmol) and potassium carbonate (5.12 g, 37.1 mmol) in N-methylpyrrolidinone (20 mL) was stirred at 120° C. for 5 h. The reaction was cooled, diluted with ethyl acetate and filtered through Celite. The filtrate was was... | COC(=O)c1ccc(N2CCOCC2)cc1Cl | null | 64.8 | null |
661,121 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | [C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])=[CH:15][C:14]=1[N+:27]([O-:29])=[O:28]>CS(C)=O>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:16]1[CH:17]=[CH:18][C:13]([CH:2]([C:1]([O:8][CH3:... | COC(=O)CC(=O)OC | COc1ccccc1-c1ccc(F)c([N+](=O)[O-])c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 100 | 0.25 | Dimethyl malonate (14 mL) was added dropwise to 2.9 g of sodium hydride suspended in 50 mL of dimethylsulfoxide. The mixture was stirred at 100° C. for 15 minutes and cooled to room temperature. Crude 4-fluoro-2′-methoxy-3-nitrobiphenyl in 60 mL of dimethylsulfoxide was added and the mixture stirred at 100° C. for 2 ho... | COC(=O)C(C(=O)OC)c1ccc(-c2ccccc2OC)cc1[N+](=O)[O-] | null | null | null |
761,300 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][O:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][CH:20]([C:25]([O:27]C)=[O:26])[C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:24][O:23][C:21]([CH:20]([CH2:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2... | COC(=O)C(Cc1ccc(OCCOc2ccc3ccccc3c2)cc1)C(=O)OC | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of dimethyl 4-[2-(2-naphthoxy)ethoxy]benzylmalonate (0.44 g, 1.07 mmol) in a mixture of methanol (4.3 ml) and tetrahydrofuran (2.1 ml) at 0° C. is added a 2 mol/L aqueous solution of sodium hydroxide (0.59 ml, 1.18 mmol). The mixture is stirred for 2 h at room temperature, and then the solvent is removed ... | COC(=O)C(Cc1ccc(OCCOc2ccc3ccccc3c2)cc1)C(=O)O | null | 82.9 | null |
1,112,474 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH3:1][O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][NH:24][CH:25]2[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.Cl[C:36]([O:38][CH3:39])=[O:37]>>[CH3:1][O:2][C:3](=[O:34])[CH2:4][C... | COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CNC2Cc3ccccc3C2)c1 | COC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the procedure described in Example 23, Step 1, using the following starting materials: [2′-(indan-2-ylaminomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester and methyl chloroformate. | COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN(C(=O)OC)C2Cc3ccccc3C2)c1 | null | null | null |
100,916 | ord_dataset-d06b137b66b3478fb6a0d41a5efd32f8 | null | 1982-01-01T00:12:00 | true | [F:1][C:2]([F:29])([F:28])[CH2:3][N:4]=[C:5]([NH2:27])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH2:26])=S)[N:11]=1.C(N(CC)CC)C>CN(C)C=O.[N+]([O-])([O-])=O.[Ag+]>[F:1][C:2]([F:29])([F:28])[CH2:3][N:4]=[C:5]([NH2:27])[NH:6][C:7]1[S:8... | NC(=NCC(F)(F)F)Nc1nc(CCCCNC(=S)Nc2ccccc2N)cs1 | null | null | [Ag+] | O=[N+]([O-])[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 2-[2-(2,2,2-trifluoroethyl)-guanidino]-4-[4-(3-[2-aminophenyl]thioureido)butyl]thiazole (0.45 g.), silver nitrate (0.34 g.) and triethylamine (0.28 ml.) in dimethylformamide (3 ml.) was stirred vigorously at ambient temperature overnight. Hydrogen sulphide gas was then bubbled through the reaction mixture ... | NC(=NCC(F)(F)F)Nc1nc(CCCCNc2nc3ccccc3[nH]2)cs1 | null | null | null |
498,734 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]([CH3:22])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH2:19][CH2:20][NH2:21])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]([CH3:22])... | O=C(Cl)Oc1ccccc1 | CN(C(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1OCCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a solution of 4-nitro-N-methyl-N-[2-(3-aminoprop-1-yloxy)phenyl]benzamide (422 mg) and triethylamine (130 mg) in dichloromethane (10 ml) was added phenyl chloroformate (201 mg) and the solution was stirred at 0° C. for 30 minutes. The reaction mixture was diluted with dichloromethane and then the organic solution wa... | CN(C(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1OCCCNC(=O)Oc1ccccc1 | null | 66.5 | null |
549,400 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:15][CH2:14][C:11]3([O:13][CH2:12]3)[CH2:10][CH2:9]2)[CH:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][C:25](=[O:29])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:12][C:11]2([OH:... | Clc1cc(N2CCC3(CC2)CO3)ncn1 | CC(C)(C)OC(=O)N1CCNC(=O)C1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | 80 | 8 | To a solution of 6-(6-chloropyrimidine-4-yl)-1-oxa-6-azaspiro[2,5]octane (4.00 g) and 4-(tert-butoxycarbonyl)-2-piperazinone (3.38 g) in tert-butylalcohol (50 ml) was added potassium tert-butoxide (0.57 g), and the mixture was stirred at 80° C. overnight. The reaction solution was concentrated, and the residue was dilu... | CC(C)(C)OC(=O)N1CCN(CC2(O)CCN(c3cc(Cl)ncn3)CC2)C(=O)C1 | null | 76.6 | null |
737,867 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:22]=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=2)[C:9]([C:23]#[N:24])=[C:8]([NH2:25])[N:7]=1)[CH3:2].[H-].[Na+].[CH3:29]I.O>CN(C=O)C>[NH2:25][C:8]1[N:7]=[C:6]([CH:5]([CH3:29])[C:4]([O:3][CH2:1][CH3:2])=[O:26])[C:11]([C:12]#[N:13])=[C... | CCOC(=O)Cc1nc(N)c(C#N)c(-c2ccc3c(c2)OCO3)c1C#N | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | 0.75 | Ethyl[6-amino-4-(1,3-benzodioxol-5-yl)-3,5-dicyano-2-pyridinyl]acetate (step 1) (2.00 g, 5.71 mmol) is initially charged in 40 ml of DMF. Sodium hydride (0.37 g, 9.19 mmol) is added and the mixture is stirred for 45 minutes. Methyl iodide (0.40 ml, 6.39 mmol) is then added, the color of the yellow reaction solution tur... | CCOC(=O)C(C)c1nc(N)c(C#N)c(-c2ccc3c(c2)OCO3)c1C#N | null | null | null |
151,995 | ord_dataset-5944a40bb4504bbe8185cfdf2a811d03 | null | 1987-01-01T00:01:00 | true | [CH2:1]([O:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]1[CH2:11][O:10]1)[CH:2]=[CH2:3].[NH2:16][C@@H:17]1[CH2:22][CH2:21][C@H:20]([N:23]2[CH2:27][CH2:26][NH:25][C:24]2=[O:28])[CH2:19][CH2:18]1.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>C(O)(C)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[C... | C=CCOc1ccccc1OCC1CO1 | N[C@H]1CC[C@@H](N2CCNC2=O)CC1 | null | O=C(O)/C=C/C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 657.6 g of 92% pure o-(allyloxy)phenoxymethyloxirane (U.S. Pat. No. 3,483,221) and 512 g of cis-1-(4-aminocyclohexyl)-2-imidazolidinone is stirred and refluxed for 6 hours in 6,000 ml of isopropanol. To the above reaction mixture, while still hot, is added 162.1 g of fumaric acid. The resulting mixture is ... | C=CCOc1ccccc1OCC(O)CN[C@H]1CC[C@@H](N2CCNC2=O)CC1 | null | null | null |
1,675,353 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16]([NH:17][C@@H:18]([C:20]([F:23])([CH3:22])[CH3:21])[CH3:19])=[C:15]([C:24]([NH2:26])=[O:25])[CH:14]=[N:13][N:12]3[CH:27]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]>C(O)C.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16]([NH:17][C@H:18]([CH3:19])[C:20]([F:23])([CH3... | C[C@@H](Nc1c(C(N)=O)cnn2cc(-c3cccc(C#N)c3)cc12)C(C)(C)F | null | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 6 | A suspension of (R)-6-(3-cyanophenyl)-4-(3-fluoro-3-methylbutan-2-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide (Example 53, 110 mg, 0.301 mmol) and Raney 3201 Nickel (17.67 mg, 0.301 mmol) in ethanol (5 mL) was bubbled with ammonia gas for 3 minutes then stirred under a balloon of hydrogen for 6 hrs. The reaction mix... | C[C@@H](Nc1c(C(N)=O)cnn2cc(-c3cccc(CN)c3)cc12)C(C)(C)F | null | 97.1 | null |
661,552 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[C:13](OCC)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]1=[O:23])(=O)C.[N:24]1([S:29]([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]1>>[N:24]1([S:29]([C:32]2[CH:38]=[CH:37][C:35]([NH:36]/[C:13](=... | CCOC(=C1C(=O)N(C(C)=O)c2ccccc21)c1ccccc1 | Nc1ccc(S(=O)(=O)N2CCCC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 1c from 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-2-indolinone and 4-(pyrrolidin-1-ylsulphonyl)-aniline. | O=C1Nc2ccccc2/C1=C(/Nc1ccc(S(=O)(=O)N2CCCC2)cc1)c1ccccc1 | null | null | null |
1,713,213 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[C:21]([N:22]4[C:30](=[O:31])[C:29]5[C:28]([C:32]#[N:33])=[CH:27][CH:26]=[CH:25][C:24]=5[CH2:23]4)=[CH:20][N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:16]3=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[BH4-].[Na+]>C(Cl)Cl.CO>[NH2:33][C... | CC(C)S(=O)(=O)c1ccc(-c2cnc3c(n2)c(N2Cc4cccc(C#N)c4C2=O)cn3C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | null | 3 | 2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]-3-oxo-isoindoline-4-carbonitrile (150 mg, 0.2143 mmol) dissolved in a mixture of DCM (10 mL) and MeOH (5 mL) under N2. CoCl2 (55.65 mg, 0.4286 mmol) added then the reaction mixture cooled in an ice bath. NaBH4 (81 mg, 2.143 mmol) added in one portion... | CC(C)S(=O)(=O)c1ccc(-c2cnc3[nH]cc(N4Cc5cccc(CN)c5C4=O)c3n2)cc1 | null | null | null |
583,957 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.Cl[C:27](=[O:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C)C1C=CN=CC=1>[CH2:1]([N:5]([C:27](=[O:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:6]1[CH:11]=[CH:... | CCOC(=O)CC(=O)Cl | CCCCNc1ccc(N2CCC(=O)CC2)cc1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 18 | A solution of 8-(4-nitro-phenyl)-1,4-dioxa-8-aza-spiro[4.5]decane (13.01 g, 49 mmol) was hydrogenated under 45 psi for one hour using 10% palladium on carbon (2.5 g) as catalyst. The reaction mixture was filtered through celite pad and the filtrate was concentrated down to give a white solid (11.46 g, 100%). This mater... | CCCCN(C(=O)CC(=O)OCC)c1ccc(N2CCC(=O)CC2)cc1 | null | 106.5 | null |
48,671 | ord_dataset-b43eb0158fd54801957aaa07bbdf3057 | null | 1978-01-01T00:11:00 | true | [F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:16]=2[NH:15][C:14](=[O:17])[CH2:13]3)=[O:7])=[CH:4][CH:3]=1.[OH-:20].[Na+]>O>[NH2:15][C:16]1[C:8]([C:6](=[O:7])[C:5]2[CH:18]=[CH:19][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]=[CH:11][C:12]=1[CH2:13][C:14]([OH:20])=[O:17] | [OH-] | O=C1Cc2cccc(C(=O)c3ccc(F)cc3)c2N1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1.5 g. (0.006 mole) of 7-(4-fluorobenzoyl) indolin-2-one in 50 ml. of 3N sodium hydroxide was refluxed under nitrogen for 45 min. The solution was cooled, diluted with an equal volume of water, filtered, and the filtrate was extracted two times with 50 ml. of ether. The aqueous basic solution was treated d... | Nc1c(CC(=O)O)cccc1C(=O)c1ccc(F)cc1 | null | null | null |
1,486,633 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:16][CH:15]3[CH2:17][N:11]4[CH2:12][CH:13]([CH2:18][CH:9]2[CH2:10]4)[CH2:14]3)[CH:5]=[N:6][CH:7]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][N:22]=1>>[CH3:19][O:20][C:21]1[N:22]=[CH:23][C:24]([C:2]2[CH:7]=[N:6][CH:5]=[C:4]([N:8]3[CH2:16][CH:15]4[CH2:17][N:11]5[CH2:12][CH:1... | Brc1cncc(N2CC3CC4CC2CN(C4)C3)c1 | COc1ccc(B(O)O)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from the product of Example 65A and 2-methoxypyridin-5-ylboronic acid according to General Method B: LC-MS Method D (ESI+) m/z 337.0 (M+H)+, retention time 1.23 minutes. | COc1ccc(-c2cncc(N3CC4CC5CC3CN(C5)C4)c2)cn1 | null | null | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.