index int64 0 919k | original_index int64 2 1.77M | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 240 ⌀ | date_of_experiment timestamp[ns] | extracted_from_file stringlengths 44 44 | grant_date timestamp[ns] | is_mapped bool 1
class | procedure_details stringlengths 13 24.5k | product_000 stringlengths 1 457 | product_001 stringlengths 1 208 ⌀ | reactant_000 stringlengths 1 696 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 stringlengths 1 285 ⌀ | rxn_str stringlengths 87 6.12k | rxn_time float64 0 1.49k ⌀ | solvent_000 stringlengths 1 64 ⌀ | solvent_001 stringlengths 1 29 ⌀ | solvent_002 stringlengths 1 29 ⌀ | temperature float64 -230 30.1k ⌀ | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
868,025 | 1,423,927 | [Cl-] | [H-] | [Na+] | null | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | 2014-01-01T00:04:00 | true | NaH (18.35 mg, 0.76 mmol) was stirred in dry THF (1 ml) at 0° C. and 2-bromo-3-(4-methoxyphenyl)-1H-indole (210 mg, 0.69 mmol) dissolved in dry THF (4.5 ml) was added dropwise. The mixture was stirred at 0° C. for 5 min and then 2,2-bis-(4-cyanatophenyl)propane (251 mg, 0.90 mmol) dissolved in dry THF (4.5 ml) was adde... | COc1ccc(-c2c(Br)n(C#N)c3ccccc23)cc1 | null | CC(C)(c1ccc(OC#N)cc1)c1ccc(OC#N)cc1 | COc1ccc(-c2c(Br)[nH]c3ccccc23)cc1 | null | [H-].[Na+].[Br:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.O(C1C=CC(C(C2C=CC(OC#N)=CC=2)(C)C)=CC=1)[C:22]#[N:23].O>C1COCC1.[Cl-].[Na+].O>[Br:3][C:4]1[N:5]([C:22]#[N:23])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C... | 0.08 | C1CCOC1 | O | null | 0 | null | 87.7 |
452,092 | 37,678 | null | null | null | null | ord_dataset-b0ddd49dad024fc7a23ae6f474f9c52f | 1978-01-01T00:03:00 | true | Using the method of Example 16, 2-benzyloxy-1,3-propane-diol (18.0 g, 0.1 mole), and 3-methoxybenzaldehyde (13.6 g, 0.1 mole) were reacted to give 26.0 g of oil which was distilled at 1 × 10-4 mm to give 20.2 g of product which distilled at a pot temperature of 200°-206° C. nmr analysis of this product indicated it to ... | COc1cccc(C2OCC(OCc3ccccc3)CO2)c1 | null | COc1cccc(C=O)c1 | OCC(CO)OCc1ccccc1 | null | [CH2:1]([O:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=O>>[CH2:1]([O:8][CH:9]1[CH2:10][O:11][CH:19]([C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([O:15][CH3:14])[CH:17]=2)[O:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH... | null | null | null | null | null | 86.6 | null |
271,097 | 536,814 | null | null | null | null | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | 2002-01-01T00:03:00 | true | In the manner described in example 3, 2-bromophenylacetic acid is condensed with 3,4-difluoroaniline to yield 2-[(3,4-difluorophenyl)amino]phenylacetic acid. | O=C(O)Cc1ccccc1Nc1ccc(F)c(F)c1 | null | Nc1ccc(F)c(F)c1 | O=C(O)Cc1ccccc1Br | null | Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[F:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[F:20])[NH2:16]>>[F:12][C:13]1[CH:14]=[C:15]([NH:16][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]([OH:11])=[O:10])[CH:17]=[CH:18][C:19]=1[F:20] | null | null | null | null | null | null | null |
525,748 | 1,655,046 | CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC | null | null | null | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | 2015-01-01T00:11:00 | true | To a toluene (112 mL) solution of the compound (5.87 g) obtained in Example 9-(1), Burgess reagent (5.322 g) was added and the mixture was heated under reflux for 2.5 hours. The reaction mixture was concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the ... | CC(C)(C)OC(=O)N1CCC[C@H]1c1nnc(CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)o1 | null | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)NNC(=O)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | null | [Si:1]([O:18][CH2:19][C:20]([NH:22][NH:23][C:24]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=O)=[O:21])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1(C)... | null | Cc1ccccc1 | null | null | null | null | 73.2 |
680,889 | 179,754 | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | [C]=O | null | null | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | 1988-01-01T00:11:00 | true | 0.5 mmoles 1-acetoxy-3-methylthiopropene (Z:E ratio 43:57) and 2.5 mmoles methanol were charged into a 71 cc stainless steel bomb equipped with a glass liner and a Teflon coated stir bar. Ten mole percent, based on 1-acetoxy-3-methylthiopropene, of a catalyst comprising bis(triphenylphosphine)dichloropalladium, (φ3P)2P... | COC(=S)C(CCSC)OC(C)=O | null | CSCC=COC(C)=O | COC(=O)C(CCSC)OC(C)=O | null | C(OC=CC[S:8]C)(=O)C.CO.[C]=O.[C:14]([O:17][CH:18]([CH2:23][CH2:24][S:25][CH3:26])[C:19]([O:21][CH3:22])=O)(=[O:16])[CH3:15]>O1CCCC1.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.C1(C)C=CC=CC=1>[C:14]([O:17][CH:18]([CH2:23][CH2:24][S:25][CH3:26])[C:19]([O:21][CH3:22])=[S:8]... | null | C1CCOC1 | CO | Cc1ccccc1 | 100 | 19.5 | null |
828,371 | 1,452,438 | [BH3-]C#N | [Na+] | null | null | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | 2014-01-01T00:07:00 | true | To a solution of N-(2-aminoethyl)-1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide E13 (50 mg, 0.16 mmol) in MeOH (5 mL) was added benzaldehyde (16 μL, 0.16 mmol). After stirring for 2 h, sodium cyanoborohydride (20 mg, 0.32 mmol) was added and the mixture was stirred for a further 20 h. The solvent was removed und... | O=C(NCCNCc1ccccc1)C1CCN(c2c(Cl)cncc2Cl)CC1 | null | O=Cc1ccccc1 | NCCNC(=O)C1CCN(c2c(Cl)cncc2Cl)CC1 | null | [NH2:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[CH:15][C:14]=2[Cl:20])[CH2:9][CH2:8]1)=[O:6].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([BH3-])#N.[Na+]>CO>[CH2:21]([NH:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:8][CH2:9][N:10]([C:13]2[C:14]([Cl:20])=[CH... | 2 | CO | null | null | null | null | 30 |
894,003 | 428,788 | O=C1CCC(=O)N1I | null | null | null | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | 1999-01-01T00:03:00 | true | A solution of 2.94 g (0.010 mol) of 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid prop-2-ynylamide in 60 ml of acetic acid was treated with 3.36 g (0.015 mol) of N-iodosuccinimide while gassing with argon. After stirring at room temperature for 46 hrs. the dark suspension obtained wa... | CCCN(CCC)Cc1cnc(-c2ncn3c2CN(C)C(=O)c2ccccc2-3)o1 | null | CCCNCCC | C#CCNC(=O)c1ncn2c1CN(C)C(=O)c1ccccc1-2 | null | [CH2:1]([NH:4][C:5]([C:7]1[N:8]=[CH:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:21])[N:13]([CH3:22])[CH2:12][C:11]=12)=[O:6])[C:2]#[CH:3].IN1C(=O)CCC1=O.[CH2:31]([NH:34][CH2:35][CH2:36][CH3:37])[CH2:32][CH3:33]>C(O)(=O)C>[CH2:31]([N:34]([CH2:3][C:2]1[O:6][C:5]([C:7]2[N:8]=[CH:9][N:10]3[C:16]4[CH:17... | 46 | CC(=O)O | null | null | 25 | null | 25.4 |
369,198 | 1,516,541 | [Cl-] | [NH4+] | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | To a solution of 9-chloro-1-(2,6-dichloro-4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (146 mg, 0.356 mmol) in tetrahydrofuran (4 mL) was added dropwise ethylmagnesium bromide (3 M solution in diethyl ether, 0.237 mL, 0.711 mmol) at 0° C., and the mixture was stirred at 0° C. for 5 min... | CCC(O)c1ccc(Cl)c2nc3n(c12)CCCN3c1c(Cl)cc(OC)cc1Cl | null | CC[Mg]Br | COc1cc(Cl)c(N2CCCn3c2nc2c(Cl)ccc(C=O)c23)c(Cl)c1 | null | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:25]=[O:26])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[C:20]([Cl:21])=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=3[Cl:24])[CH2:12][CH2:13][CH2:14][N:7]21.[CH2:27]([Mg]Br)[CH3:28]>O1CCCC1.[Cl-].[NH4+]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:16]([Cl:24])=[CH:17][C:18]([O:22][CH3:... | 0.08 | C1CCOC1 | null | null | 0 | 87.4 | null |
666,909 | 130,230 | null | null | null | null | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | 1985-01-01T00:05:00 | true | Prepared analogously to Example 1 from 6-(4-chlorobutoxy)-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 3,4-dimethylthiophenol. | Cc1ccc(SCCCCOc2ccc3c(c2)C(C)(C)OC(=O)N3)cc1C | null | Cc1ccc(S)cc1C | CC1(C)OC(=O)Nc2ccc(OCCCCCl)cc21 | null | Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][C:14](=[O:16])[O:13][C:12]([CH3:18])([CH3:17])[C:11]=2[CH:19]=1.[CH3:20][C:21]1[CH:22]=[C:23]([SH:28])[CH:24]=[CH:25][C:26]=1[CH3:27]>>[CH3:20][C:21]1[CH:22]=[C:23]([S:28][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:8]=[CH:9][C:10]3[NH:15][C:14](=[O:16]... | null | null | null | null | null | null | null |
702,227 | 660,962 | null | null | null | null | ord_dataset-04d607efe1d9485eb99fafa06880f62e | 2005-01-01T00:02:00 | true | 2,2-Dimethyl-6-formylchromane was condensed with 5-chloro-2-oxindole to give 0.3 g of 5-Chloro-3-(2,2-dimethylchroman-6-ylmethylene)-1,3-dihydroindol-2-one as a yellow-orange solid. | CC1(C)CCc2cc(C=C3C(=O)Nc4ccc(Cl)cc43)ccc2O1 | null | O=C1Cc2cc(Cl)ccc2N1 | CC1(C)CCc2cc(C=O)ccc2O1 | null | [CH3:1][C:2]1([CH3:14])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:12]=O)[CH:8]=2)[O:3]1.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH2:19]2>>[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[CH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3... | null | null | null | null | null | null | null |
714,564 | 267,148 | null | null | null | null | ord_dataset-134cf2fa32ab464880d75db06c38f35a | 1993-01-01T00:05:00 | true | The title compound is prepared by the procedure of Example 28 using 0.750 g of product from Example 58 and 12.13 g of methyl iodide. The residue is recrystallized from methyl alcohol to give 0.90 g of the desired product as colorless needles. | CCCCCCCCCCCCCCOc1ccc(C(=O)NCCc2cccc[n+]2C)cc1 | [I-] | CCCCCCCCCCCCCCOc1ccc(C(=O)NCCc2ccccn2)cc1 | CI | null | [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10](=[O:32])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=1.[CH3:33][I:34]>>[I-:34].[CH3:33][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][... | null | null | null | null | null | 90.7 | null |
721,164 | 367,885 | [Pd] | null | null | null | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | 1997-01-01T00:06:00 | true | A mixture of 3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-nitro-1H-indole (3.55 g, 10.34 mmol) and 10% palladium on carbon (0.55 g) in absolute ethanol (60 mL) was shaken under a hydrogen atmosphere (3 atm) for 7 hours at room temperature. The resulting reaction mixture was filtered through diatomaceous earth,... | CC(C)(C)OC(=O)N1CCC(c2c[nH]c3ccc(N)cc23)CC1 | null | CC(C)(C)OC(=O)N1CC=C(c2c[nH]c3ccc([N+](=O)[O-])cc23)CC1 | null | null | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=3)[NH:16][CH:15]=2)=[CH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[NH2:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([C... | 7 | CCO | null | null | 25 | null | 78.5 |
400,516 | 854,565 | Cl | OO | [Na+] | null | ord_dataset-faa0236be76c4501841c954527cd1b6c | 2008-01-01T00:12:00 | true | A solution of 1-(4-methoxyphenyl)cyclohexanecarbonitrile (E2) (1.092 g, 5.07 mmol) in dioxane (6 ml) to a mixture of 2 M NaOH in water (150 ml) and 30% H2O2 in water (7.5 ml) was added and the resultant suspension was stirred under reflux for 4 days. The pH of the reaction medium was brought to pH 1 with conc. HCl (ca.... | COc1ccc(C2(C(=O)O)CCCCC2)cc1 | null | O | COc1ccc(C2(C#N)CCCCC2)cc1 | [OH-] | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]#N)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-:17].[Na+].Cl.[OH2:20]>O1CCOCC1.OO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([OH:20])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1 | null | C1COCCO1 | null | null | null | null | 71 |
68,504 | 176,175 | CSC(=NC#N)SC | NCCCOc1cccc(CN2CCCCC2)c1 | null | null | ord_dataset-07db50a3ce6941919df30a9e2898988f | 1988-01-01T00:08:00 | true | Similarly prepared from 3-[3-(1-piperidinylmethyl)phenoxy]propanamine] (10 g) and cyanocarbonimidodithioic acid, dimethyl ester (5.84 g) was N'-cyano-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]carbamimidothioic acid methyl ester (11.5 g) m.p. 89°-90°. | CSC(=NC#N)NCCCOc1cccc(CN(C)C)c1 | null | CSC(=NC#N)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | N1(CC2C=C(C=CC=2)OCCCN)CCCCC1.C(N=C(SC)SC)#N.[CH3:27][S:28][C:29](=[N:48][C:49]#[N:50])[NH:30][CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][N:42]2[CH2:47]CCC[CH2:43]2)[CH:36]=1>>[C:49]([N:48]=[C:29]([S:28][CH3:27])[NH:30][CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C... | null | null | null | null | null | null | null |
784,359 | 585,164 | CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1Cc2ccccc2C[C@H]1C(=O)O | [Mg+2] | [OH-] | null | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | 2003-01-01T00:03:00 | true | In the liquid mixture, the 10.0 g of quinapril hydrochloride reacted with 1.23 g of magnesium hydroxide to produce 9.47 g of quinapril magnesium plus 1.00 g of magnesium chloride, plus 0.76 g of water. The liquid was then filtered to remove the excess magnesium hydroxide. | [Cl-] | [Mg] | Cl | null | null | [CH3:1][CH2:2][O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:20]1[C@H:29]([C:30]([OH:32])=[O:31])[CH2:28][C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:21]1)=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5].[ClH:33].[OH-].[Mg+2:35].[OH-]>O>[CH3:1][CH2:2][O:3][C:4]([C@@H:6]([NH:15][C@... | null | O | null | null | null | null | null |
180,539 | 79,274 | null | null | null | null | ord_dataset-0c37e633e9814a6e886187796cacf216 | 1981-01-01T00:03:00 | true | 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum et... | Clc1cccc(Br)c1CBr | null | Cc1c(Cl)cccc1Br | O=C1CCC(=O)N1Br | null | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][Br:10] | null | ClC(Cl)(Cl)Cl | null | null | null | null | null |
652,015 | 934,719 | null | null | null | null | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | 2010-01-01T00:01:00 | true | N-[4-chloro-3-(trifluoromethyl)phenyl]-4-(4-methoxyphenyl)butanamide was prepared as described in Example 5, Step 1 using 4-(4-methoxyphenyl)butyric acid and 4-chloro-3-(trifluoromethyl)aniline. LCMS, AA: Rt=2.17 min, [MH− 370.1]. | COc1ccc(CCCC(=O)Nc2ccc(Cl)c(C(F)(F)F)c2)cc1 | null | Nc1ccc(Cl)c(C(F)(F)F)c1 | COc1ccc(CCCC(=O)O)cc1 | null | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[C:23]([F:26])([F:25])[F:24]>>[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)... | null | null | null | null | null | null | null |
327,743 | 1,687,572 | null | null | null | null | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | 2016-01-01T00:02:00 | true | To a solution of 2-hydroxy-3-methyl-benzoic acid (10 g, 66.7 mmol, 1.0 eq) in acetic acid (100 mL) was added bromine (10.66 g, 66.7 mmol, 1.0 eq) slowly over 5 min. The mixture was stirred at room temperature for 24 h, then water was added slowly and the mixture was stirred for a further 30 min. The precipitate was col... | Cc1cc(Br)cc(C(=O)O)c1O | null | BrBr | Cc1cccc(C(=O)O)c1O | null | [OH:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]Br.O>C(O)(=O)C>[Br:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:2]([OH:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5] | 24 | CC(=O)O | O | null | 25 | null | 88.9 |
690,799 | 584,356 | null | null | null | null | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | 2003-01-01T00:03:00 | true | Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.976 g, 4.02 mmol) and 4-nitrophenyl isothiocyanate (0.723 g, 4.02 mmol) to afford the product (1.39 g) after trituration in ether; m.p. 183-184° C. | COc1ccc(C(=O)Nc2ccccc2)cc1NC(=S)Nc1ccc([N+](=O)[O-])cc1 | null | O=[N+]([O-])c1ccc(N=C=S)cc1 | COc1ccc(C(=O)Nc2ccccc2)cc1N | null | [NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[S:30])=[CH:24][CH:23]=1)([O-:21])=[O:20]>CCOCC>[CH3:18][O:17][C:16]1[CH:15]=[CH:14][C:4]([C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH... | null | CCOCC | null | null | null | null | 81.8 |
182,931 | 1,575,689 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-9741bb5fd93044078df2a45f45733054 | 2015-01-01T00:04:00 | true | To a solution of Example 227A (0.521 g, 1.91 mmol) in dioxane (10 mL) at ambient temperature was added 2-(t-butyldimethylsilyl)thiophene-5-boronic acid pinacol ester (0.619 g, 1.91 mmol), 2 molar cesium carbonate (0.9 mL, 1.9 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex... | CC(C)[C@H](CO)NCc1cccc(-c2ccc([Si](C)(C)C(C)(C)C)s2)n1 | null | CC1(C)OB(c2ccc([Si](C)(C)C(C)(C)C)s2)OC1(C)C | CC(C)[C@H](CO)NCc1cccc(Br)n1 | null | Br[C:2]1[N:7]=[C:6]([CH2:8][NH:9][C@H:10]([CH:13]([CH3:15])[CH3:14])[CH2:11][OH:12])[CH:5]=[CH:4][CH:3]=1.[Si:16]([C:23]1[S:24][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:27]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[Si:16]([C:23]1[S:24][C:25]([C:2]2[N:7]=[C:6]([CH2:8][NH... | null | C1COCCO1 | null | null | 80 | null | 47.6 |
825,057 | 834,637 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-ec576c604a9d47258c87c732a043ec71 | 2008-01-01T00:08:00 | true | A mixture of 1-[2-(4-cyclopropylmethylpiperazin-1-yl)phenyl]-3,3,5,5-tetramethylcyclohexanol (250 mg, 0.675 mmol) produced in Example (108b), water (0.12 mL) and trifluoroacetic acid (1.04 mL, 13.5 mmol) was stirred for 21 hours at an external temperature of room temperature. Aqueous solution of potassium carbonate was... | CC1(C)C=C(c2ccccc2N2CCN(CC3CC3)CC2)CC(C)(C)C1 | null | CC1(C)CC(C)(C)CC(O)(c2ccccc2N2CCN(CC3CC3)CC2)C1 | null | null | [CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]3(O)[CH2:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19]([CH3:26])([CH3:25])[CH2:18]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH:1]1([CH2:4][N:5]2[CH2:6][CH2:7][N:8]([C:11]3[CH:16]=[CH:15][CH:14]... | 21 | O=C(O)C(F)(F)F | O | null | 25 | null | 91.6 |
522,180 | 790,513 | O=P([O-])([O-])[O-] | [H-] | [Na+] | null | ord_dataset-530502f8e61e455784f93c5faa45c94b | 2007-01-01T00:09:00 | true | Sodium hydride (60% dispersion in mineral oil, 145 mg) was added portionwise to a solution of 4-(2-hydroxyethyl)phenol (502 mg) in THF (15 ml) and the mixture was stirred at 20° C. for 30 min. tert-Butyldimethylsilyl chloride (547 mg) was added and the mixture was stirred for 75 min. Phosphate buffer solution (pH 6.5) ... | CC(C)(C)[Si](C)(C)Oc1ccc(CCO)cc1 | null | CC(C)(C)[Si](C)(C)Cl | OCCc1ccc(O)cc1 | null | [H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].P([O-])([O-])([O-])=O>C1COCC1>[Si:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][OH:3])=[CH:7][CH:8]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14] | 1.25 | C1CCOC1 | null | null | null | 71.8 | null |
646,556 | 1,754,512 | CC(=O)O[BH-](OC(C)=O)OC(C)=O | Cl | [Na+] | null | ord_dataset-97eb2ab57fec4160922caae33b54d956 | 2016-01-01T00:08:00 | true | Sodium triacetoxyborohydride (0.30 g, 1.4 mmol) was added to a solution of 5-(tert-butyl)-2-hydroxy-3-(6-(trifluoromethyl)pyridin-3-yl)benzaldehyde (0.35 g, 1.1 mmol) and 1-methyl piperazine (0.14 mL, 1.3 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature under nitrogen for 16 hours.... | CN1CCN(Cc2cc(C(C)(C)C)cc(-c3ccc(C(F)(F)F)nc3)c2O)CC1 | null | CC(C)(C)c1cc(C=O)c(O)c(-c2ccc(C(F)(F)F)nc2)c1 | CN1CCNCC1 | null | C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([C:19]1[CH:20]=[C:21]([C:28]2[CH:29]=[N:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:33]=2)[C:22]([OH:27])=[C:23]([CH:26]=1)[CH:24]=O)([CH3:18])([CH3:17])[CH3:16].[CH3:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.C(O)C.[ClH:48]>O1CCCC1>[ClH:48].[ClH:48].[C:15]([C:... | 16 | CCO | C1CCOC1 | null | 25 | 53 | null |
885,127 | 308,913 | CCN=C=NCCCN(C)C | Cl | null | null | ord_dataset-acbdbaa766314b66a982823354e82bf2 | 1995-01-01T00:04:00 | true | A solution of ethyl 2-ethyl-3-[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.72 g), monoethyl malonate (0.94 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.02 g), triethylamine (1.78 g) in dichloromethane (20 ml) is stirred overnight at room temp... | CCOC(=O)CC(=O)N1CCc2nc(CC)n(Cc3ccc(-c4ccccc4C(=O)OC(C)(C)C)cc3)c2C1C(=O)OCC | null | CCOC(=O)CC(=O)[O-] | CCOC(=O)C1NCCc2nc(CC)n(Cc3ccc(-c4ccccc4C(=O)OC(C)(C)C)cc3)c21 | null | [CH2:1]([C:3]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:20][CH:19]=2)[C:6]2[CH:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][CH2:9][CH2:10][C:5]=2[N:4]=1)[CH3:2].[C:37]([O:43][CH2:44][CH3:45])(=[O:42])[CH2:38][... | null | CCN(CC)CC | ClCCl | null | null | 74 | null |
651,508 | 1,289,836 | null | null | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | To a cooled (−20° C.) solution of tert-butyl 4-[4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (914 mg. 2.28 mmol) in DMF (12.6 mL) and AcOH (5 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (326 mg, 1.14 mmol) in 3 portions over 10 minutes. The mixture was stirred at 0° C. for ... | CC(C)(C)OC(=O)N1CCC(c2nc(-c3cc(Br)c4c(N)ncnn34)cs2)CC1 | null | CC(C)(C)OC(=O)N1CCC(c2nc(-c3ccc4c(N)ncnn34)cs2)CC1 | CC1(C)C(=O)N(Br)C(=O)N1Br | null | [NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[N:12]=[C:13]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]4)[S:14][CH:15]=3)[N:6]2[N:5]=[CH:4][N:3]=1.[Br:29]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C.CC(O)=O>[NH2:1][C:2]1[C:7]2=[C:8]([Br:29])[CH:9]=[C:10]([C:11]3[N:12]=[C... | 3 | CC(=O)O | CN(C)C=O | null | 0 | null | 109.1 |
784,660 | 1,583,993 | [K+] | [OH-] | null | null | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | 2015-01-01T00:05:00 | true | To a solution of 2-tosyl-1H-indole (199 mg, 0.73 mmol) in 3 mL DMF was added 1,4-dibromobutane (263 μL, 2.20 mmol) in 1 mL DMF and KOH (41 mg, 0.73 mmol), and the reaction stirred at room temperature 1.75 h. The reaction mixture was then partitioned between water and ether, and the aqueous layer extracted twice with et... | Cc1ccc(S(=O)(=O)c2cc3ccccc3n2CCCCBr)cc1 | null | BrCCCCBr | Cc1ccc(S(=O)(=O)c2cc3ccccc3[nH]2)cc1 | null | [S:1]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Br:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.[OH-].[K+]>CN(C=O)C>[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:11]1[S:1]([... | 1.75 | CN(C)C=O | null | null | 25 | null | null |
447,776 | 756,682 | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | I[Cu]I | null | null | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | 2007-01-01T00:02:00 | true | 3-Iodo-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine (0.114 g, 0.25 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (0.040 g, 0.30 mmol) and triethyl amine (NEt3) (0.125 ml) are dissolved in THF (1 ml) and copper iodide (CuI) (0.0048 g, 0.025 mmol) is added under stirring. After passing a stream of ar... | FC(F)(F)c1ccc(C=Cc2nc(COc3ccc(C#CCCn4ccnn4)nn3)co2)cc1 | null | C#CCCn1ccnn1 | FC(F)(F)c1ccc(C=Cc2nc(COc3ccc(I)nn3)co2)cc1 | null | I[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[N:11]=[C:12]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[O:13][CH:14]=2)=[CH:6][CH:7]=1.[CH2:27]([N:31]1[CH:35]=[CH:34][N:33]=[N:32]1)[CH2:28][C:29]#[CH:30].C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1... | 3 | CCOC(C)=O | CCN(CC)CC | C1CCOC1 | null | null | null |
145,828 | 642,872 | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | 2004-01-01T00:07:00 | true | 4-[4-(4-tert-Butylphenyl)-4-oxo-2-(4-trifluoromethoxyphenyl)butyryl]benzoic acid (10.4 g, 20.86 mmol) was dissolved in DMF (150 mL) and added EDAC (5.60 g, 29.20) and HOBt (4.23 g, 31.29 mmol). After ½ h a solution of beta-alanine methyl ester hydrochloride (4.37 g, 31.29 mmol) and DIPEA (5.36 mL, 31.29 mmol) in DMF (2... | COC(=O)CCNC(=O)c1ccc(C(=O)C(CC(=O)c2ccc(C(C)(C)C)cc2)c2ccc(OC(F)(F)F)cc2)cc1 | null | COC(=O)CCN | CC(C)(C)c1ccc(C(=O)CC(C(=O)c2ccc(C(=O)O)cc2)c2ccc(OC(F)(F)F)cc2)cc1 | null | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:36])[CH2:12][CH:13]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[C:14]([C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=2)=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:59][O:60]... | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | 104.8 |
485,880 | 648,473 | null | null | null | null | ord_dataset-5d77a731aa10488794c824ad12021f57 | 2004-01-01T00:09:00 | true | Prepared from 6-methoxy-2-indolinone (prepared according to Quallich, G. J.; Morrissey, P. M.; Synthesis 1993, 51) and acetic anhydride | COc1ccc2c(c1)N(C(C)=O)C(=O)C2 | null | CC(=O)OC(C)=O | COc1ccc2c(c1)NC(=O)C2 | null | [CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[C:13]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][C:8]1=[O:12])(=[O:15])[CH3:14] | null | null | null | null | null | null | null |
265,549 | 257,499 | CC#CCOC(=N)C(Cl)(Cl)Cl | O=S(=O)(O)C(F)(F)F | null | null | ord_dataset-2369b9b9f44641b1930518c59ae89a95 | 1992-01-01T00:11:00 | true | To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4",3"-dihydroxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (50 mg in 1.5 ml 33% methylene chloride in cyclohexane) is added 2-butynyl trichloroacetimidate (20 μl neat) and th... | CC#CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CC1O | null | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC | null | null | [CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:52])=[CH:43][CH:44]2[CH2:49][... | null | null | null | null | 25 | null | null |
676,138 | 1,741,733 | C[C@@H](Oc1nc(-c2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)c(F)c2)cc2ncn(C3CC3)c12)[C@H]1CNC(=O)C1 | null | null | null | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | 2016-01-01T00:06:00 | true | Following the procedure described for intermediate from Step-3 in Example 3.100, starting from combined (R)-4-((R)-1-((5-bromo-1-cyclopropyl-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one (250 mg, 0.69 mmol) and tert-butyl 4-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate (... | C[C@@H](Oc1cc(-c2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)c(F)c2)cc2ncn(C3CC3)c12)[C@H]1CNC(=O)C1 | null | CC(C)(C)OC(=O)N1CCN(c2ccc(B3OC(C)(C)C(C)(C)O3)cc2F)CC1 | C[C@@H](Oc1cc(Br)cc2ncn(C3CC3)c12)[C@H]1CNC(=O)C1 | null | Br[C:2]1[CH:13]=[C:12]([O:14][C@@H:15]([C@H:17]2[CH2:21][NH:20][C:19](=[O:22])[CH2:18]2)[CH3:16])[C:5]2[N:6]([CH:9]3[CH2:11][CH2:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[F:23][C:24]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:26][C:25]=1[N:39]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[... | null | null | null | null | null | null | null |
13,912 | 339,331 | Cl | null | null | null | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | 1996-01-01T00:09:00 | true | 5 ml of a 4N solution of hydrogen chloride in dioxane were added to a solution of 0.91 g of 1-t-butoxycarbonyl-2-(2-{2-[2-(4-ethylphenyl)ethyl]phenoxy}ethyl)piperidine [prepared as described in step (a) above] in 5 ml of dioxane, and the resulting solution was allowed to stand at room temperature for 1 hour. At the end... | CCc1ccc(CCc2ccccc2OCCC2CCCCN2)cc1 | null | CCc1ccc(CCc2ccccc2OCCC2CCCCN2C(=O)OC(C)(C)C)cc1 | null | null | [ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[CH2:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[C... | 1 | C1COCCO1 | null | null | null | 88 | null |
697,727 | 1,710,360 | Cl | null | null | null | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | 2016-01-01T00:04:00 | true | A mixture of tert-butyl 3-hydroxy-1-oxa-7-azaspiro[4.4]nonane-7-carboxylate (CAN 1331825-50-3, 33 mg, 136 μmol) and a 4 M solution of HCl in dioxane (339 μL, 1.36 mmol) in dioxane (0.3 mL) was stirred at ambient temperature for 3 h to give the title compound (14 mg, 58%) as light brown oil which was sufficiently pure t... | OC1COC2(CCNC2)C1 | null | CC(C)(C)OC(=O)N1CCC2(CC(O)CO2)C1 | null | null | [OH:1][CH:2]1[CH2:6][C:5]2([CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]2)[O:4][CH2:3]1.[ClH:18]>O1CCOCC1>[ClH:18].[O:4]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7]2)[CH2:6][CH:2]([OH:1])[CH2:3]1 | null | C1COCCO1 | null | null | null | 58 | null |
894,900 | 844,174 | null | null | null | null | ord_dataset-e2b35e721c2741999b0005d12691f9fe | 2008-01-01T00:10:00 | true | The title compound is prepared from 2-chloro-N-(4-methoxy-phenyl)-acetamide [J. Heterocycl. Chem., 32, 1429. (1995)] and 4-benzyl-piperidine according to the method described in Example 143b. Melting Point: 81-83° C. (hexane) | COc1ccc(NC(=O)CN2CCC(Cc3ccccc3)CC2)cc1 | null | c1ccc(CC2CCNCC2)cc1 | COc1ccc(NC(=O)CCl)cc1 | null | Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[O:4].[CH2:14]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCCC>[CH2:14]([CH:21]1[CH2:26][CH2:25][N:24]([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)=[O:4... | null | CCCCCC | null | null | null | null | null |
140,505 | 1,666,444 | [Au] | CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C | null | null | ord_dataset-9cc455db05a444779921f786a45b21a6 | 2015-01-01T00:12:00 | true | A gold (Ag(I)) catalyst {[Au(JohnPhos)NCCH3]|SbF6—} [JohnPhos:(2-biphenyl)di-tert-butylphosphine] (11.3 mg, 0.015 mmol) was put into a reaction container, and dichloroethane (0.4 mL) was put thereinto. After stirring at room temperature for 5 minutes, ethyl hydrogen hex-1-ynylphosphonate (57.0 mg, 0.3 mmol) diluted wit... | CCCCC1=CP(=O)(OCC)OC(C2CCCCC2)=C1 | null | C#CC1CCCCC1 | CCCCC#CP(=O)(O)OCC | null | CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.[C:22]([P:28](=[O:33])([OH:32])[O:29][CH2:30][CH3:31])#[C:23][CH2:24][CH2:25][CH2:26][CH3:27].[C:34]([CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)#[CH:35]>[Au].ClC(Cl)C>[CH2:30]([O:29][P:28]1(=[O:32])[CH:22]=[C:23]([CH2:24][CH2:25][CH2:26][CH3:27])[CH:35]=[C:34]([CH:36]2... | 0.08 | CC(Cl)Cl | null | null | 25 | null | 47 |
291,225 | 439,576 | null | null | null | null | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | 1999-01-01T00:09:00 | true | A solution of 7.5 g of (4-hydroxy-phenoxy)-acetonitrile dissolved in 60 ml of nitromethane was cooled in an ice bath and 3.88 ml of 70% nitric acid was added dropwise. After 45 minutes, the reaction mixture was poured into ethyl acetate, washed with brine, dried (MgSO4), and evaporated to dryness. The crude product was... | N#CCOc1ccc(O)c([N+](=O)[O-])c1 | null | N#CCOc1ccc(O)cc1 | O=[N+]([O-])O | null | [OH:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13].C(OCC)(=O)C>[N+](C)([O-])=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13] | 0.75 | CCOC(C)=O | C[N+](=O)[O-] | null | null | null | null |
695,863 | 945,863 | [Na+] | null | null | null | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | 2010-01-01T00:03:00 | true | A solution of biphenyl-2-ylcarbamic acid 1-(2-{[3-(2-aminoethylcarbamoyl)benzoyl]methylamino}ethyl)piperidin-4-yl ester (9.31 g, 17.1 mmol; prepared as described in Preparation 8) and 4-hydroxybenzaldehyde10,411,879 (2.30 g, 18.8 mmol, 1.1 eq) in 125 mL MeOH was stirred at room temperature for 2 hours. Na(OAc)3BH (7.26... | O=C(Nc1ccccc1-c1ccccc1)OC1CCN(CCNCC(=O)c2cccc(C(=O)NCCNCc3ccc(O)cc3)c2)CC1 | null | NCCNC(=O)c1cccc(C(=O)CNCCN2CCC(OC(=O)Nc3ccccc3-c3ccccc3)CC2)c1 | CC(=O)O[BH-](OC(C)=O)OC(C)=O | null | [NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[C:9]([CH:38]=[CH:39][CH:40]=1)[C:10]([CH2:12][NH:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([O:22][C:23](=[O:37])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:18][CH2:17]1)=[O:11])=[O:6].[BH-](O[C:51]([CH3:53... | null | CO | null | null | null | null | null |
636,695 | 1,353,608 | null | null | null | null | ord_dataset-6034127657614f02860ed057b62b882e | 2013-01-01T00:10:00 | true | A 50 mL round bottom flask was charged with 8-methoxy-5-(thiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine (0.30 g, 1.3 mmol) and POCl3 (3 mL). The mixture was heated at 130° C. overnight. TLC indicated a complete conversion. Work-up: the reaction mixture was concentrated in vacuo. The residue was carefully poured into ice... | Clc1ncc(-c2cccs2)n2cnnc12 | null | O=P(Cl)(Cl)Cl | COc1ncc(-c2cccs2)n2cnnc12 | null | CO[C:3]1[C:4]2[N:5]([CH:14]=[N:15][N:16]=2)[C:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:7][N:8]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:3]1[C:4]2[N:5]([CH:14]=[N:15][N:16]=2)[C:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:7][N:8]=1 | null | null | null | null | 130 | null | 75 |
551,929 | 676,796 | O=C([O-])O | [Na+] | null | null | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | 2005-01-01T00:07:00 | true | To a solution of 1 g (20S)-4,4,20-trimethyl-pregna-8,14-dien-3β,21-diol in 10 ml dichloromethane 5.4 ml of a 0.5 M Dess-Martin-Periodinane solution were added at room temperature. The mixture was stirred for one hour, poured into saturated sodium bicarbonate solution, extracted with ethyl acetate and washed with brine.... | C[C@H](C=O)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3 | null | C[C@H](CO)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3 | null | null | [CH3:1][C:2]1([CH3:26])[C@@H:22]([OH:23])[CH2:21][CH2:20][C@@:19]2([CH3:24])[CH:3]1[CH2:4][CH2:5][C:6]1[C:7]3[C@:15]([CH3:25])([CH2:16][CH2:17][C:18]=12)[C@@H:10]([C@H:11]([CH3:14])[CH2:12][OH:13])[CH2:9][CH:8]=3.C(=O)(O)[O-].[Na+]>ClCCl>[OH:23][C@H:22]1[CH2:21][CH2:20][C@@:19]2([CH3:24])[CH:3]([CH2:4][CH2:5][C:6]3[C:7... | 1 | ClCCl | null | null | null | null | 23.1 |
76,590 | 210,892 | null | null | null | null | ord_dataset-e0a818f9350b46cdb184d2ac404ede9f | 1990-01-01T00:06:00 | true | A mixture of 3-amino-4-(4'-cyanophenyl)aminopyridine (9.31 g, 44.3 mmol), triethyl-orthoacetate (40 ml) and acetic anhydride (30 ml) was heated at reflux for 2 hours under nitrogen, cooled, then concentrated under reduced pressure. The brown residue was dissolved in 1M hydrochloric acid and washed with ethyl acetate (2... | Cc1nc2cnccc2n1-c1ccc(C#N)cc1 | null | N#Cc1ccc(Nc2ccncc2N)cc1 | CCC(CC)(CC)C([O-])([O-])[O-] | null | [NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1.[CH2:17](C(CC)(CC)C([O-])([O-])[O-])[CH3:18]>C(OC(=O)C)(=O)C>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=[C:17]2[CH3:18])=[CH:10][CH:11]=1)#[N:16] | null | CC(=O)OC(C)=O | null | null | null | null | null |
307,925 | 1,576,362 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-9741bb5fd93044078df2a45f45733054 | 2015-01-01T00:04:00 | true | To the crude material from Step 1 was added DMF (1.5 ml) followed by cesium carbonate (175 mg, 0.538 mmol) and bromoacetonitrile (24.99 μl, 0.359 mmol). The resulting mixture was stirred at 60° C. overnight affording clean conversion to desired product according to LC-MS. The mixture was filtered through Celite with th... | COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(-c4ccc(Cl)cc4OCC#N)nccc3c2)cc1 | null | COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(-c4ccc(Cl)cc4O)nccc3c2)cc1 | N#CCBr | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([N:21]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[C:4]([OH:36])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:44][C:45]#[N:46]... | 8 | CN(C)C=O | null | null | 60 | null | null |
733,951 | 1,501,396 | null | null | null | null | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | 2014-01-01T00:10:00 | true | To a solution of methyl 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-cyclobutyl-4-ethylbenzoate (compound 215.5, 2.15 g, 4.99 mmol, 1.00 equiv) in methanol (20 mL), was added hydrazine hydrate (80%, 15 mL) batchwise. The reaction was stirred at 80° C. overnight. After cooling to ambient temperature, the mixture was con... | CCc1cc(C2CCC2)c(C(=O)NN)cc1C(=O)N1CCC(c2ccc(C#N)cc2)CC1 | null | NN | CCc1cc(C2CCC2)c(C(=O)OC)cc1C(=O)N1CCC(c2ccc(C#N)cc2)CC1 | null | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:18]([CH2:31][CH3:32])=[CH:19][C:20]([CH:27]4[CH2:30][CH2:29][CH2:28]4)=[C:21]([CH:26]=3)[C:22]([O:24]C)=O)=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].O.[NH2:34][NH2:35]>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:1... | 8 | O | CO | null | 80 | null | 53 |
201,383 | 406,263 | null | null | null | null | ord_dataset-55e306db9b6b4befbc22504c12b7113d | 1998-01-01T00:06:00 | true | A solution of 1.17 g of the compound obtained in EXAMPLE 222 in 7.5 ml of DCM is cooled to +4° C., 15 ml of TFA are added and the reaction mixture is stirred for 3 hours 15 minutes at +4° C. It is concentrated under vacuum, the residue is taken up with DCM and the solvent is evaporated off under vacuum, this operation ... | CCN(CC)C(=O)N1CCc2cc(S(=O)(=O)N3C(=O)C(NCCC4CCNCC4)(c4ccccc4Cl)c4cc(Cl)ccc43)ccc21 | O | CCC(C)(CC)NC(=O)N1CCc2cc(S(=O)(=O)N3C(=O)C(NCCC4CCN(C(=O)OC(C)(C)C)CC4)(c4ccccc4Cl)c4cc(Cl)ccc43)ccc21 | null | null | C([O:5]C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17]2([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[Cl:55])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[N:19]([S:27]([C:30]3[CH:31]=[C:32]4[C:36](=[CH:37][CH:38]=3)[N:35]([C:39]([NH:41][C:42]([CH2:46]C)(CC)C)=[O:40])[CH2:34][CH2:33]4)(=[O:29])=[... | 0.25 | O=C(O)C(F)(F)F | ClCCl | null | null | null | null |
364,774 | 1,260,598 | COc1ccc2c(O)cc(-c3nc(C(C)C)cs3)nc2c1 | null | null | null | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | 2013-01-01T00:02:00 | true | Compound 269a was synthesized from compound 268a (3.50 g, 1 eq) as an orange solid in 84% yield, following the procedure as described for compound 218a (80° C. overnight). 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.04-1.07 (m, 4H), 2.13-2.18 (m, 1H), 4.06 (s, 3H), 6.75 (s, 1H), 7.06 (d, J=9.10 Hz, 1H), 7.09 (s, 1H), 8.27 (d, J... | COc1ccc2c(O)cc(-c3nc(C4CC4)cs3)nc2c1Cl | null | COc1ccc(C(C)=O)c(NC(=O)c2nc(C3CC3)cs2)c1Cl | null | null | [C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[S:14][CH:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[N:17]=2)=O)=[C:8]([Cl:21])[C:7]([O:22][CH3:23])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(C1N=C(C2C=C(O)C3C(=CC(OC)=CC=3)N=2)SC=1)(C)C>>[Cl:21][C:8]1[C:7]([O:22][CH3:23])=[CH:6][CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([C:13]1[S:14][CH:15]=[C:16]([CH... | null | null | null | null | null | null | 84 |
315,188 | 464,334 | [Li]CCCC | null | null | null | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | 2000-01-01T00:05:00 | true | To a solution of 2.4 mL (18.49 mmol, 1.5 eq) of isopropylamine in 50 mL of dry THF at -78° C. under argon is added 9.3 mL (14.8 mmol, 1.2 eq) of 1.6 M BuLi in hexanes solution. This is stirred at -78° C. for 1 hour at which time 1.8 mL (13.56 mmol, 1.1 eq) of methyl isovalerate is added dropwise. This mixture is stirre... | COC(=O)CC(O)(CCCCc1ccccc1)C(C)C | null | COC(=O)CC(C)C | O=CCCCCc1ccccc1 | CC(C)N | [CH:1](N)([CH3:3])[CH3:2].[Li]CCCC.[C:10]([O:16][CH3:17])(=[O:15])[CH2:11]C(C)C.[C:18]1([CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[O:29])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[OH:29][C:28]([CH:1]([CH3:3])[CH3:2])([CH2:27][CH2:26][CH2:25][CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:11][C:10]([O:16... | 1 | C1CCOC1 | null | null | -78 | null | null |
391,019 | 188,591 | null | null | null | null | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | 1989-01-01T00:04:00 | true | 0.53 gram of daunorubicin in a free base is dissolved in 100 ml of methylene chloride. 1 ml of ethyl acetylacetate is added to the solution by constant stirring. The entire mixture is agitated for 12 hours at room temperature in a nitrogenic atmosphere. The reaction is checked by means of thin-layer chromatography on a... | CCOC(=O)/C=C(\C)N[C@H]1C[C@H](O[C@H]2C[C@](O)(C(C)=O)Cc3c(O)c4c(c(O)c32)C(=O)c2c(OC)cccc2C4=O)O[C@@H](C)[C@H]1O | null | COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)=O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 | CCOC(=O)CC(C)=O | null | [CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3=[C:15]([OH:32])[C:16]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]=5[O:30][CH3:31])[C:20](=[O:21])[C:17]=4[C:18]([OH:19])=[C:13]3[CH2:12][C@@:11]([OH:36])([C:33]([CH3:35])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:37])[C@@H:3]1[OH:38].[C:39]([CH2:42][C:43]([O... | 12 | Cc1ccccc1 | ClCCl | CC(C)=O | 25 | null | null |
547,502 | 846,200 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-e2b35e721c2741999b0005d12691f9fe | 2008-01-01T00:10:00 | true | A mixture of 6-bromopicolinic acid (2.02 g, 10 mmol), phenyboronic acid (1.22 g, 10 mmol), cesium carbonate (5.00 g) and PdCl2[(t-Bu)2P(OH)]2 (70 mg, CombiPhos Catalysts, Inc. Princeton, N.J.) in DMF (20 mL) and water (3 mL) was purged with Ar-gas and heated at 110° C. for 24 h. The reaction was incomplete and did not ... | O=C(O)c1cccc(-c2ccccc2)n1 | null | O=C(O)c1cccc(Br)n1 | OB(O)c1ccccc1 | null | Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[C:11]1([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1 | null | CN(C)C=O | O | null | 110 | 17.6 | null |
412,512 | 97,457 | null | null | null | null | ord_dataset-0bf72e95d80743729fdbb8b57a4bc0c6 | 1982-01-01T00:08:00 | true | 7β-[D-2-Amino-2-(4-hydroxyphenyl)acetamido]-7α-methoxy-3-(1-methyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid trifluoroacetic acid salt (150 mg) was subjected to suspension into ethyl acetate (7.5 ml) and was added thereto with stirring at 0° C. N,O-bis(trimethylsilyl) acetamide (417 μl). To the resulting mixtu... | O=C(Cl)c1coc2cc(O)c(O)cc2c1=O | null | C/C(=N\[Si](C)(C)C)O[Si](C)(C)C | O=C(Cl)c1c(O)oc2cccc(O)c2c1=O | CCOC(C)=O | [CH3:1]/[C:2](/[O:8][Si](C)(C)C)=N\[Si](C)(C)C.O[C:14]1C=C[CH:21]=[C:20]2[C:15]=1[C:16](=[O:28])[C:17]([C:25]([Cl:27])=[O:26])=[C:18](O)[O:19]2.C(OCC)(=[O:31])C>>[OH:31][C:1]1[CH:14]=[C:15]2[C:20](=[CH:21][C:2]=1[OH:8])[O:19][CH:18]=[C:17]([C:25]([Cl:27])=[O:26])[C:16]2=[O:28] | null | null | null | null | 0 | null | null |
154,444 | 1,581,377 | null | null | null | null | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | 2015-01-01T00:05:00 | true | Phenyl isoquinolin-1-ylcarbamate (80 mg, 0.30 mmol) and (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (87 mg, 0.32 mmol) was dissolved in dimethyl sulfoxide. Then triethylamine (0.08 mL, 0.61 mmol) was added to it. The mixture was stirred at room temperature for 12 h. The reaction mixture was ... | CC1CCN(c2nc(C(F)(F)F)ccc2CNC(=O)Nc2nccc3ccccc23)CC1 | null | O=C(Nc1nccc2ccccc12)Oc1ccccc1 | CC1CCN(c2nc(C(F)(F)F)ccc2CN)CC1 | null | [C:1]1([NH:11][C:12](=[O:20])OC2C=CC=CC=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH3:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=[C:30]([C:36]([F:39])([F:38])[F:37])[N:29]=2)[CH2:24][CH2:23]1.C(N(CC)CC)C>CS(C)=O.O>[C:1]1([NH:11][C:12]([NH:35][CH2:34][C:33]2[... | 12 | CS(C)=O | CCN(CC)CC | O | 25 | null | 34.6 |
817,996 | 138,075 | null | null | null | null | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | 1985-01-01T00:12:00 | true | One g of 1-[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]-4-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperazine is dissolved in 15 ml of pyridine and cooled in an ice bath to 0°-5° C. Acetic anhydride (0.6 g) is slowly added and the reaction mixture is stirred for 2 hr. After the addition of 100 ml of water, the reaction mi... | CC(=O)OC(CN1CCN(CC(=O)Nc2c(C)cccc2C)CC1)C1COc2ccccc2O1 | null | Cc1cccc(C)c1NC(=O)CN1CCN(CC(O)C2COc3ccccc3O2)CC1 | CC(=O)OC(C)=O | null | [O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH:11]([OH:31])[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:30])=[O:21])[CH2:15][CH2:14]1.[C:32](OC(=O)C)(=[O:34])[CH3:33].O>N1C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5... | 2 | c1ccncc1 | O | null | null | null | null |
29,387 | 549,182 | CC(=O)[O-] | Cl | [Na+] | null | ord_dataset-e967d076b4894c2c854795f019ed3c39 | 2002-01-01T00:06:00 | true | 4-Dimethylamino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione was prepared by the procedure of Example 1 from 3-dimethylaminophthalic anhydride (1.34 g, 7.0 mmol), 3-aminopiperidine-2,6-dione hydrogen chloride (1.15 g, 7.0 mmol) and sodium acetate (0.60 g, 7.3 mmol) in acetic acid (20 mL). The product was a yellow so... | CN(C)c1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O | null | NC1CCC(=O)NC1=O | CN(C)c1cccc2c1C(=O)OC2=O | null | [CH3:1][N:2]([CH3:14])[C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:6]([O:8][C:9](=[O:10])[C:4]=12)=O.Cl.[NH2:16][CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[NH:19][C:18]1=[O:24].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:14][N:2]([CH3:1])[C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:4]=1[C:9](=[O:10])[N:16]([CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[... | null | CC(=O)O | null | null | null | null | null |
38,134 | 1,143,744 | null | null | null | null | ord_dataset-68715347640045adb1b09e6a04722b0e | 2012-01-01T00:03:00 | true | 5-bromo-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one was prepared from 5-bromopyridin-2(1H)-one and 2,2,2-trifluoroethyl trifluoromethanesulfonate following a procedure analogous to that described in Example 59 Step 1. | O=c1ccc(Br)cn1CC(F)(F)F | null | O=c1ccc(Br)c[nH]1 | O=S(=O)(OCC(F)(F)F)C(F)(F)F | null | [Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.FC(F)(F)S(O[CH2:15][C:16]([F:19])([F:18])[F:17])(=O)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:15][C:16]([F:19])([F:18])[F:17])[CH:7]=1 | null | null | null | null | null | null | null |
90,373 | 427,050 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | 1999-01-01T00:03:00 | true | 2.1 g of 7-(4,6-dimethoxypyrimidin-2-yl)-4-(2-furyl)-7-hydroxyfuro[3,4-b]pyridin-5(7H)one was weighed out, and 50 ml of N,N-dimethylformamide and 0.82 g of potassium carbonate were added thereto. The mixture was stirred at room temperature. 0.8 g of methyl iodide was added thereto dropwise, and the mixture was stirred ... | COC(=O)c1c(-c2ccco2)ccnc1C(=O)c1nc(OC)cc(OC)n1 | null | CN(C)C=O | COc1cc(OC)nc(C2(O)OC(=O)c3c(-c4ccco4)ccnc32)n1 | null | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2([OH:26])[C:15]3=[N:16][CH:17]=[CH:18][C:19]([C:20]4[O:21][CH:22]=[CH:23][CH:24]=4)=[C:14]3[C:13](=[O:25])[O:12]2)[N:4]=1.[CH3:27]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].CI>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([C:15]2[N:16]=[CH:17][C... | null | O | CI | null | 25 | null | 50.7 |
23,117 | 1,513,904 | null | null | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | Ammonia in methanol (7 N solution, 15 mL) was added dropwise to stirred neat 2,4-dichloro-5-(trifluoromethyl)pyrimidine 131 (5.0 g, 23.04 mmol) under argon, and the resulting mixture was stirred at RT for 2 h. The reaction mixture was quenched with water and then extracted with ethyl acetate (2×200 mL). The combined or... | Nc1ncc(C(F)(F)F)c(Cl)n1 | null | N | FC(F)(F)c1cnc(Cl)nc1Cl | null | [NH3:1].Cl[C:3]1[N:8]=[C:7]([Cl:9])[C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1>CO>[Cl:9][C:7]1[C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=[C:3]([NH2:1])[N:8]=1 | 2 | CO | null | null | 25 | null | null |
719,689 | 717,503 | O=C([O-])O | [Na+] | null | null | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | 2006-01-01T00:07:00 | true | Into 4.0 mL of chloroform was dissolved 200 mg of Compound 19, and 194 mg of benzyltrimethylammonium tribromide was added, followed by 1 hour of stirring at room temperature. The reaction was terminated by adding water to the reaction solution and then the solvent was once removed by evaporation. The residue was adjust... | Cc1nc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)cs1 | null | CC(N)=S | Cc1c(S(=O)(=O)Nc2ccc(C(=O)CBr)cc2S(C)(=O)=O)sc2ccc(F)cc12 | null | Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([C:15]2[S:19][C:18]3[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:17]=3[C:16]=2[CH3:25])(=[O:14])=[O:13])=[C:7]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:6]=1)=O.O1CCOCC1.C(=O)([O-])O.[Na+].[C:41]([NH2:44])(=[S:43])[CH3:42]>C(O)C>[F:24][C:22]1[CH:21]=[CH:20][C:18]2[S:19][C:15... | 2 | CCO | C1COCCO1 | null | null | 42.6 | null |
133,151 | 921,749 | null | null | null | null | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | 2009-01-01T00:11:00 | true | To a chilled suspension of 3-aminobenzyl alcohol (9.24 g, 75 mmol) in THF (50 mL) was added neat acetic anhydride (8.1 mL, 86 mmol). The reaction mixture was stirred cold for 1 hr, diluted with EtOAc, washed with aq. NaOH and brine, and concentrated in vacuo to give N-[3-(hydroxymethyl)phenyl]acetamide (10.5 g, 85%). | CC(=O)Nc1cccc(CO)c1 | null | Nc1cccc(CO)c1 | CC(=O)OC(C)=O | null | [NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1COCC1.CCOC(C)=O>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([NH:1][C:10](=[O:12])[CH3:11])[CH:9]=[CH:8][CH:7]=1 | 1 | C1CCOC1 | CCOC(C)=O | null | null | null | 84.8 |
807,901 | 434,485 | null | null | null | null | ord_dataset-386da077ab2340638cada986e2ef0770 | 1999-01-01T00:07:00 | true | By the same procedure as described in the example 1, synthesis was carried out starting with 4-[1-[3-(ethylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid and using 2-(ethylamino)ethanol. Then, the product was recrystallized using ethyl acetate and hexane to give the desired compound. | CCNc1cccnc1N1CCN(C(=O)c2ccc(C(=O)N(CC)CCO)cc2)CC1 | null | CCNCCO | CCNc1cccnc1N1CCN(C(=O)c2ccc(C(=O)O)cc2)CC1 | null | [CH2:1]([NH:3][C:4]1[C:5]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=3)=[O:17])[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].[CH2:27]([NH:29][CH2:30][CH2:31][OH:32])[CH3:28]>>[CH2:27]([N:29]([CH2:30][CH2:31][OH:32])[C:22]([C:21]1[CH:20]=[CH:19][C:18]([C:1... | null | null | null | null | null | 72 | null |
278,261 | 824,240 | [BH4-] | [Na+] | null | null | ord_dataset-0ca5627a13c049a99463095023b09fe5 | 2008-01-01T00:06:00 | true | A solution of Example 227 (1.0 equiv) in MeOH (0.2 M solution) was treated with formaldehyde (5 equiv) and stirred at room temperature (r.t.) for 2 hours. Sodium Borohydride was added and stirred at r.t. overnight. The solvent was removed under vacuum and crude residue was purified by silica gel chromatography using th... | Cc1cc(CN(C)CCC(C)C)ccc1Oc1ccc(C(N)=O)cn1 | null | C=O | Cc1cc(CNCCC(C)C)ccc1Oc1ccc(C(N)=O)cn1 | null | [CH3:1][C:2]1[CH:17]=[C:16]([CH2:18][NH:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=1.[CH2:25]=O.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:17]=[C:16]([CH2:18][N:19]([CH3:25])[CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:15]=[CH:14][C:3]=1... | 2 | CO | null | null | 25 | 20 | null |
145,812 | 107,881 | [Na+] | [OH-] | null | null | ord_dataset-29d79fca4cec4a43b773d0ba25b27651 | 1983-01-01T00:08:00 | true | A solution of ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 3.6 g.), 2 N aqueous solution of sodium hydroxide (14.1 ml.), tetrahydrofuran (14.1 ml.) and methanol (15 ml.) was stirred at 40° C. for 1.5 hours. The resultant solution was concentrated in vacuo, and the residue was dissolved in water. Af... | C=CCON=C(C(=O)O)c1csc(N)n1 | null | C=CCON=C(C(=O)OCC)c1csc(N)n1 | null | null | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH:16]=[CH2:17])[C:8]([O:10]CC)=[O:9])[N:6]=1.[OH-].[Na+].O1CCCC1>CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH:16]=[CH2:17])[C:8]([OH:10])=[O:9])[N:6]=1 | null | CO | C1CCOC1 | null | null | null | 59.6 |
162,516 | 1,278,911 | null | null | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | Following a procedure analogous to the procedure described in Example 1 using 2-aminoethyl-methyl-sulfone (923 mg, 7.49 mmol) and N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide (400 mg, 0.749 mmol) the title compound was obtained as a white solid (27 mg, 4% y... | CS(=O)(=O)CCNc1nccc(-c2sc(N3CCCC3)nc2-c2cccc(NS(=O)(=O)c3c(F)cccc3F)c2)n1 | null | CS(=O)(=O)CCN | O=S(=O)(Nc1cccc(-c2nc(N3CCCC3)sc2-c2ccnc(Cl)n2)c1)c1c(F)cccc1F | null | [NH2:1][CH2:2][CH2:3][S:4]([CH3:7])(=[O:6])=[O:5].Cl[C:9]1[N:14]=[C:13]([C:15]2[S:19][C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[N:17][C:16]=2[C:25]2[CH:26]=[C:27]([NH:31][S:32]([C:35]3[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=3[F:42])(=[O:34])=[O:33])[CH:28]=[CH:29][CH:30]=2)[CH:12]=[CH:11][N:10]=1>>[F:42][C:3... | null | null | null | null | null | null | null |
432,958 | 310,655 | O=S(=O)([O-])O | [K+] | null | null | ord_dataset-081613ef79bd4110aacc146b4465f086 | 1995-01-01T00:05:00 | true | A solution of 1.5 g (5. mmol) of 1-[2-(4-fluorophenyl) cyclopenten-1-yl]-4-(methylthio)benzene (Step 3) in 46 mL of methanol/thf (1:1) was slowly treated with 5.2 g (8.4 mmol) of Oxone® [2 KHSO5.KHSO4.K2SO4 ] in 23 mL of water. After stirring for 4 h, the solvent was removed in vacuo. The residue was dissolved in ethyl... | CS(=O)(=O)c1ccc(C2=C(c3ccc(F)cc3)CCC2)cc1 | null | O=S([O-])OO | CSc1ccc(C2=C(c3ccc(F)cc3)CCC2)cc1 | CO | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:13]2[CH:18]=[CH:17][C:16](SC)=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.O[O:22][S:23]([O-:25])=O.[K+].OS([O-])(=O)=O.[K+].[CH3:33]O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:13]2[CH:14]=[CH:15][C:16]([S:23]([CH3:33])(=[O:25])=[O:... | 4 | O | null | null | null | null | 54 |
746,562 | 1,038,375 | null | null | null | null | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | 2011-01-01T00:03:00 | true | The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate was reacted with (4-fluoro-2-methylbenzyl)magnesium bromide) according to General Procedure 3. The resulting product was then converted to the title compound by hydrogenation according to General Pr... | COC(=O)c1cc2c([nH]1)CCC2Cc1ccc(F)cc1C | null | COC(=O)c1cc2c([nH]1)CCC2=O | Cc1cc(F)ccc1C[Mg]Br | null | O=[C:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=2[CH2:4][CH2:3]1.[F:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][Mg]Br)=[C:17]([CH3:24])[CH:16]=1>>[F:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][CH:2]2[C:9]3[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=3[CH2:4][CH2:3]2)=[C:17]([CH3:24])[CH:16]=1 | null | null | null | null | null | null | null |
91,633 | 1,183,466 | CC(C)(C)[O-] | O=C(O)CC(O)(CC(=O)O)C(=O)O | [K+] | null | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | 2012-01-01T00:07:00 | true | N-BOC-4-hydroxy-L-proline (A; 281 mg; 1.21 mmol) was dissolved in dimethylsulfoxide (3 mL) at room temperature then potassium t-butoxide (270 mg; 2.4 mmol) was added. The resulting solution was stirred at room temperature for 2 hours, then cooled to 0° C. A solution of 1-chloro-6-methoxy-3-methylisoquinoline in dimethy... | COc1ccc2c(O[C@@H]3C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C3)nc(C)cc2c1 | null | CC(C)(C)OC(=O)N1CC(O)C[C@H]1C(=O)O | COc1ccc2c(Cl)nc(C)cc2c1 | null | [C:1]([N:8]1[CH2:15][CH:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)([O-])C.[K+].Cl[C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=2)[CH:27]=[C:26]([CH3:36])[N:25]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[C:4]([O:3][C:1]([N:8]1[CH2:15][C@H:14]([O... | 2 | CS(C)=O | null | null | 25 | null | null |
512,201 | 637,984 | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | ord_dataset-a192df1b44174b5886ef2005f759d553 | 2004-01-01T00:05:00 | true | 44 g (167 mmol) of triphenylphosphine were added to a solution of 24 g (152 mmol) of 5-hydroxymethyl-3-methylthiophene-2-carbonitrile in 180 ml of tetrahydrofuran. Then, a solution of 55 g (167 mmol) of tetrabromomethane in 100 ml of tetrahydrofuran was added. The mixture was stirred for 90 minutes at room temperature.... | Cc1cc(CBr)sc1C#N | null | Cc1cc(CO)sc1C#N | BrC(Br)(Br)Br | null | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[S:26][C:25]([C:27]#[N:28])=[C:24]([CH3:29])[CH:23]=1.[Br:30]C(Br)(Br)Br>O1CCCC1>[Br:30][CH2:21][C:22]1[S:26][C:25]([C:27]#[N:28])=[C:24]([CH3:29])[CH:23]=1 | 1.5 | C1CCOC1 | null | null | 25 | null | null |
353,778 | 19,200 | [Cu] | null | null | null | ord_dataset-8ca24382d55b4303bc34393399f4110e | 1977-01-01T00:01:00 | true | 4-Iodophenyl acetate (7.86 g, 0.030 mole), 1,17-diiodoperfluoro-3,6,9,15-tetraoxaheptadecane (9.68 g, 0.010 mole), and copper bronze (5.08 g, 0.080 g atom) were stirred together under nitrogen at 113°-117° C for 48 hours. The cooled reaction mixture was added to 200 ml of ether. The cuprous salts and excess copper were... | CC(=O)Oc1ccc(C(F)(F)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)c2ccc(OC(C)=O)cc2)cc1 | null | CC(=O)Oc1ccc(I)cc1 | FC(F)(I)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)I | CC(=O)OC(C)=O | [C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].I[C:13]([F:56])([F:55])[C:14]([F:54])([F:53])[O:15][C:16]([F:52])([F:51])[C:17]([F:50])([F:49])[O:18][C:19]([F:48])([F:47])[C:20]([F:46])([F:45])[O:21][C:22]([F:44])([F:43])[C:23]([F:42])([F:41])[C:24]([F:40])([F:39])[C:25]([F:38])([F:37])[C:26]([F:... | null | CCOCC | null | null | null | null | null |
902,464 | 1,154,343 | Cl | O=C(n1ccnc1)n1ccnc1 | null | null | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | 2012-01-01T00:04:00 | true | Treat a solution of 3′-chloro-4′-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid (0.2 g, 0.34 mmol) in CH2Cl2 (15 mL) with 1,1′-carbonyldiimidazole (0.11 g, 0.68 mmol) and stir for 1 hour at room temperature. Treat the reaction with 4,4-difluoropiperidine hydrochlori... | CC(C)[Si](OC1CCN(N2CC[C@@H](Cc3ccc(-c4ccc(C(=O)N5CCC(F)(F)CC5)cc4)cc3Cl)C2=O)CC1)(C(C)C)C(C)C | null | FC1(F)CCNCC1 | CC(C)[Si](OC1CCN(N2CCC(Cc3ccc(-c4ccc(C(=O)O)cc4)cc3Cl)C2=O)CC1)(C(C)C)C(C)C | null | [Cl:1][C:2]1[CH:3]=[C:4]([C:32]2[CH:37]=[CH:36][C:35]([C:38](O)=[O:39])=[CH:34][CH:33]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]2)[C:10]1=[O:31].C(N1C=CN=C1)(N1C=... | 1 | ClCCl | CCN(C(C)C)C(C)C | CCOC(C)=O | 25 | 64.1 | null |
916,829 | 820,137 | Cl | null | null | null | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | 2008-01-01T00:05:00 | true | To a solution of 2-ethyl-4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-oxazole (2.57 g) in methanol (30 mL) was added concentrated hydrochloric acid (1.33 mL) at room temperature, and the mixture was stirred at 50° C. for 1 hr. The reaction mixture was evaporated under reduced pressure, and the res... | CCc1nc(/C=C/c2cn(-c3ccccc3)nc2O)co1 | null | CCc1nc(/C=C/c2cn(-c3ccccc3)nc2OCOC)co1 | null | null | [CH2:1]([C:3]1[O:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[C:11]([O:21]COC)=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[N:7]=1)[CH3:2].[ClH:25]>CO>[ClH:25].[CH2:1]([C:3]1[O:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[C:11]([OH:21])=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[... | 1 | CO | null | null | 50 | 90 | null |
457,009 | 969,809 | C[Al](C)C | Cl | null | null | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | 2010-01-01T00:06:00 | true | Morpholine (269 μl, 3.08 mmol) was dissolved in dichloromethane (3 ml), and under nitrogen atmosphere at room temperature, trimethylaluminium (1.03 M hexane solution, 2.99 ml, 3.08 mmol) was added. After stirring at the same temperature for 15 minutes, a solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxaz... | Cc1c(-c2ccccc2)c(F)c2oc(C(=O)N3CCOCC3)nc2c1C#N | null | C1COCCN1 | CCOC(=O)c1nc2c(C#N)c(C)c(-c3ccccc3)c(F)c2o1 | null | [NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C[Al](C)C.[C:11]([C:13]1[C:18]2[N:19]=[C:20]([C:22](OCC)=[O:23])[O:21][C:17]=2[C:16]([F:27])=[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14]=1[CH3:34])#[N:12].Cl>ClCCl>[F:27][C:16]1[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:14]([CH3:34])[C:13]([C:11]... | 0.25 | ClCCl | null | null | null | null | 81.8 |
432,970 | 336,425 | null | null | null | null | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | 1996-01-01T00:08:00 | true | Indole-2-carboxylic acid was coupled to the resultant compound of Example 173 using the carbodiimide coupling procedure of Example 55 to provide the desired compound. | CC(C)[C@H](NC(=O)c1cc2ccccc2[nH]1)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)[C@H](O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)c1cc2ccccc2[nH]1)C(C)C | null | N=C=N | CC(C)[C@H](N)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)[C@H](O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)C(C)C | O=C(O)c1cc2ccccc2[nH]1 | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.[NH2:13][C@H:14]([C:18]([NH:20][C@H:21]([C@@H:29]([OH:48])[C@H:30]([OH:47])[C@@H:31]([NH:39][C:40](=[O:46])[C@H:41]([CH:43]([CH3:45])[CH3:44])[NH2:42])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:2... | null | null | null | null | null | null | null |
694,883 | 178,224 | null | null | null | null | ord_dataset-4d84abdf99524e0fb6c42ab2a3300790 | 1988-01-01T00:10:00 | true | Prepared by the method described in Example 1 from N,N'-bis(4-methoxyphenyl)thiourea (11.5 g, 40 mmoles) and acetylenedicarboxylic acid (4.6 g, 40 mmoles). Recrystallization from methanol gave the product (10.1 g), mp 184°-187° C. | COc1ccc(N=C2SC(=CC(=O)O)C(=O)N2c2ccc(OC)cc2)cc1 | null | O=C(O)C#CC(=O)O | COc1ccc(NC(=S)Nc2ccc(OC)cc2)cc1 | null | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[S:11])=[CH:5][CH:4]=1.[C:21]([C:26](O)=[O:27])#[C:22][C:23]([OH:25])=[O:24]>>[O:27]=[C:26]1[C:21](=[CH:22][C:23]([OH:25])=[O:24])[S:11][C:10](=[N:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]... | null | null | null | null | null | null | 65.7 |
161,570 | 1,081,215 | C[O-] | Cl | [Na+] | null | ord_dataset-afd812677c134591a99f46ce28de2524 | 2011-01-01T00:08:00 | true | A mixture of ethyl 4,4-difluoro-3-oxobutanoate (5.0 g), butanimidamide hydrochloride (4.1 g) and sodium methoxide (28% methanol solution, 15 mL) in methanol (50 mL) was stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid, dried over sodium sulfate and concentrated. ... | CCCc1nc(C(F)F)cc(=O)[nH]1 | null | CCOC(=O)CC(=O)C(F)F | CCCC(=N)N | null | [F:1][CH:2]([F:11])[C:3](=O)[CH2:4][C:5]([O:7]CC)=O.Cl.[C:13](=[NH:18])([NH2:17])[CH2:14][CH2:15][CH3:16].C[O-].[Na+]>CO.C(OCC)(=O)C>[F:11][CH:2]([F:1])[C:3]1[N:17]=[C:13]([CH2:14][CH2:15][CH3:16])[NH:18][C:5](=[O:7])[CH:4]=1 | 8 | CCOC(C)=O | CO | null | null | null | 98.9 |
3,418 | 1,743,480 | null | null | null | null | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | 2016-01-01T00:07:00 | true | To a mixture of N-(3-(1H-pyrazol-4-yl)-5-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide (50 mg, 0.081 mmol) in DCM (10 mL) was added TFA (1 mL, 12.98 mmol). The mixture was stirred at 25° C. for 2 h. The mixture was concentrated and NH4OH (0.5 mL) was added. Then ... | CCOc1cc(-c2ccc(CC(=O)Nc3cc(-c4cn[nH]c4)cc(C(F)(F)F)c3)c(F)c2)c[nH]c1=O | Cl | ClCCl | CCOc1cc(-c2ccc(CC(=O)Nc3cc(-c4cn[nH]c4)cc(C(F)(F)F)c3)c(F)c2)cnc1OCc1ccc(OC)cc1 | null | [NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([NH:16][C:17](=[O:45])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:26]=[N:27][C:28]([O:34]CC5C=CC(OC)=CC=5)=[C:29]([O:31][CH2:32][CH3:33])[CH:30]=4)=[CH:21][C:20]=3[F:44])[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)[CH:3]=[N:2]1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:54]>>[ClH:54].... | 2 | O=C(O)C(F)(F)F | null | null | 25 | 15.9 | null |
416,362 | 1,607,329 | null | null | null | null | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | 2015-01-01T00:07:00 | true | The title compound was prepared using methods analogous to those described in Example 376 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazin-2-amine and 3-bromo-2-(isopropylthio)pyridine. MS (ESI): mass calcd. for C18H17FN4S, 340.12; m/z found, 341.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.62-8... | CC(C)Sc1ncccc1-c1ccc(-c2cnc(N)cn2)c(F)c1 | null | CC(C)Sc1ncccc1Br | CC1(C)OB(c2ccc(-c3cnc(N)cn3)c(F)c2)OC1(C)C | null | [F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[C:26]([S:31][CH:32]([CH3:34])[CH3:33])=[N:27][CH:28]=[CH:29][CH:30]=1>>[F:1][C:2]1[CH:7]=[C:6]([C:25]2[C:26]([S:31][CH:32]([CH3:34])[CH3:33])=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:5]=[CH:4][C:3]=... | null | null | null | null | null | null | null |
350,079 | 83,960 | O=C([O-])O | [Na+] | null | null | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | 1981-01-01T00:07:00 | true | For example, p-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate is reacted with phenylacetyl chloride in cold aqueous acetone containing sodium bicarbonate to provide p-nitrobenzyl 7-phenylacetamido-3-chloro-3-cephem-4-carboxylate. | O=C(Cc1ccccc1)NC1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(Cl)CS[C@H]12 | null | O=C(Cl)Cc1ccccc1 | NC1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(Cl)CS[C@H]12 | null | [NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12.[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)(O)[O-].[Na+]>CC(C)=O>[C:25]1([CH2:31][C:32]([NH:1][CH:2]2[C:23]... | null | CC(C)=O | null | null | null | null | null |
902,244 | 313,407 | null | null | null | null | ord_dataset-abe42048f0b84fa88446cee56a31e967 | 1995-01-01T00:07:00 | true | Dissolve ethyl-4-[4-(phenylmethyl)-1-piperazinyl]-benzo[b]thiophene-2-carboxylate (2.00 g, 5.26 mmol, prepared in example 1) in 1,2-dichloroethane (40 mL) under an atmosphere of nitrogen and cool the solution with an ice bath. Add 1-chloroethyl chloroformate (1.40 mL, 13.1 mmol) and warm the reaction to room temperatur... | CCOC(=O)c1cc2c(N3CCNCC3)cccc2s1 | Cl | CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2s1 | CC(Cl)OC(=O)Cl | null | [CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([N:15]3[CH2:20][CH2:19][N:18](CC4C=CC=CC=4)[CH2:17][CH2:16]3)[C:8]=2[CH:7]=1)=[O:5])[CH3:2].[Cl:28]C(OC(Cl)C)=O>ClCCCl>[ClH:28].[N:15]1([C:14]2[C:8]3[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:10][C:9]=3[CH:11]=[CH:12][CH:13]=2)[CH2:20][CH2:19][NH:... | 0.5 | ClCCCl | null | null | null | null | 66.3 |
741,529 | 151,850 | [Na+] | null | null | null | ord_dataset-5944a40bb4504bbe8185cfdf2a811d03 | 1987-01-01T00:01:00 | true | 195.5 g of 1 was added, drop-by-drop over 45 minutes, to a stirred mixture of 164 g of anhydrous sodium acetate and 1.8 liters of dimethylformamide, at 130° C. The mixture was held at 130° C. for an additional 2.25 hours, then most of the solvent was evaporated under reduced pressure and the cooled residue and treated ... | CC(=O)OCC1CN(Cc2ccccc2)C1 | null | ClCC1CN(Cc2ccccc2)C1 | CC(=O)[O-] | null | [CH2:1]([N:8]1[CH2:11][CH:10]([CH2:12]Cl)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O-:17])(=[O:16])[CH3:15].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:11][CH:10]([CH2:12][O:17][C:14](=[O:16])[CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | 2.25 | CN(C)C=O | null | null | null | null | null |
79,236 | 949,302 | Cl[Sn]Cl | null | null | null | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | 2010-01-01T00:04:00 | true | Reduction of 4,6-dichloro-N-cyclopropyl-3-hydroxy-2-nitrobenzamide with tin (II) chloride hydrate using the conditions as described in Step B yielded 2-amino-4,6-dichloro-N-cyclopropyl-3-hydroxybenzamide (93%).—1H NMR (CD3OD): δ 6.67 (s, 1H), 2.86 (m, 1H), 0.79 (m, 2H), 0.62 (m, 2H). | Nc1c(O)c(Cl)cc(Cl)c1C(=O)NC1CC1 | null | O=C(NC1CC1)c1c(Cl)cc(Cl)c(O)c1[N+](=O)[O-] | null | null | [Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:5]([C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[O:7])=[C:4]([N+:15]([O-])=O)[C:3]=1[OH:18].O.[Sn](Cl)Cl>>[NH2:15][C:4]1[C:3]([OH:18])=[C:2]([Cl:1])[CH:13]=[C:12]([Cl:14])[C:5]=1[C:6]([NH:8][CH:9]1[CH2:11][CH2:10]1)=[O:7] | null | O | null | null | null | 93 | null |
262,533 | 979,884 | C[O-] | [Na+] | null | null | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | 2010-01-01T00:07:00 | true | A solution of sodium methoxide in MeOH (30 wt %, 202.2 g) was added to absolute EtOH (360 mL) followed by 1,3-dimethyluracil (75 g) and 2-cyano-N-phenyl-thioacetamide (Adhikari et al, Australian J. Chem., 1999, 52, 63-67) (90 g). The resulting mixture was heated at reflux for 8 h and then allowed to cool to ambient tem... | N#Cc1ccc(=O)n(-c2ccccc2)c1[S-] | null | N#CCC(=S)Nc1ccccc1 | Cn1ccc(=O)n(C)c1=O | null | C[O-].[Na+:3].CCO.CN1[CH:15]=[CH:14][C:12](=[O:13])N(C)C1=O.[C:17]([CH2:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[S:21])#[N:18]>CO>[C:17]([C:19]1[CH:15]=[CH:14][C:12](=[O:13])[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]=1[S-:21])#[N:18].[Na+:3] | null | CCO | CO | null | 25 | null | null |
731,176 | 264,922 | null | null | null | null | ord_dataset-a7bd0db0684c464bb02ff6a36065fee3 | 1993-01-01T00:03:00 | true | A mixture of 2-[(ethoxycarbonyl)amino]benzoic acid ethyl ester (65.75 g, 0.277 mol) and 2-aminoethanol (16.9 g, 0.277 mol) was refluxed for 2.5 days in 350 mL of xylenes. The reaction was cooled to room temperature and xylene was removed. Chloroform was added to the residue and a brown solid crystallized. The brown sol... | O=c1[nH]c2ccccc2c(=O)n1CCO | null | NCCO | CCOC(=O)Nc1ccccc1C(=O)OCC | null | C(O[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([O:14]CC)=O)C.[NH2:18][CH2:19][CH2:20][OH:21]>>[OH:21][CH2:20][CH2:19][N:18]1[C:4](=[O:17])[C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:11][C:12]1=[O:14] | null | null | null | null | 25 | null | 71.3 |
291,874 | 470,644 | null | null | null | null | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | 2000-01-01T00:07:00 | true | 3-Iodoaniline (8.50 mL) and diethyl ethoxymethylenemalonate (14.30 mL) are heated at 130° C. for 1 hour. The reaction is cooled to room temperature and 70 mL diphenyl ether is added. The solution is heated at 250° C. for 1.5 hours with removal of ethanol by a Dean-Stark trap. The reaction is cooled to room temperature ... | O=C(NCc1ccc(Cl)cc1)c1cnc2cc(I)ccc2c1O | null | NCc1ccc(Cl)cc1 | CCOC(=O)c1cnc2cc(I)ccc2c1O | null | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=O.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>C(OCC)C>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:13]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[C:8]([I:12])[CH:7]=3)=... | null | CCOCC | null | null | 180 | null | null |
760,379 | 1,368,319 | Oc1cc(C2CCC3(CC2)OCCO3)nc2ccnn12 | null | null | null | ord_dataset-d932d1d683704a8bad3d064bcb197acc | 2013-01-01T00:11:00 | true | tert-Butyl 4-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate was synthesized in a manner similar to the synthesis of 7-chloro-5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidine, but with tert-butyl 4-(7-hydroxypyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate substituted for 5-(1,4-dioxaspi... | CC(C)(C)OC(=O)N1CCC(c2cc(Cl)n3nccc3n2)CC1 | null | CC(C)(C)OC(=O)N1CCC(c2cc(O)n3nccc3n2)CC1 | Clc1cc(C2CCC3(CC2)OCCO3)nc2ccnn12 | null | [Cl:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH:11]2[CH2:20][CH2:19]C3(OCCO3)[CH2:13][CH2:12]2)[CH:3]=1.OC1N2N=CC=C2N=C(C2CC[N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])CC2)C=1.O1C2(CCC(C3C=C(O)N4N=CC=C4N=3)CC2)OCC1>>[Cl:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH:11]2[CH2:12][... | null | null | null | null | null | null | null |
752,773 | 574,695 | C[C@H](N)C(=O)O | Cl | Clc1nc2ccccc2s1 | null | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | 2002-01-01T00:12:00 | true | Following General Procedure B and using 2-chlorobenzothiazole (Aldrich) and L-alanine (Aldrich), N-(benzothiazol-2-yl)-L-alanine was prepared. This compound was then coupled to L-norleucine methyl ester hydrochloride (Sigma) using General Procedure D (without the 1N HCl wash) to provide for the title compound as a soli... | CCCC[C@H](NC(=O)[C@H](C)Nc1nc2ccccc2s1)C(=O)OC | null | CCCC[C@H](N)C(=O)OC | C[C@H](Nc1nc2ccccc2s1)C(=O)O | null | ClC1SC2C=CC=CC=2N=1.N[C@H](C(O)=O)C.[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[NH:26][C@H:27]([C:29]([OH:31])=O)[CH3:28].Cl.[CH3:33][O:34][C:35](=[O:42])[C@H:36]([CH2:38][CH2:39][CH2:40][CH3:41])[NH2:37].Cl>>[CH3:33][O:34][C:35](=[O:42])[C@@H:36]([NH:37][C:29](=[O:31])[C@H:27]([CH3:28])[NH:26][C... | null | null | null | null | null | null | null |
267,354 | 278,044 | [BH4-] | [Na+] | null | null | ord_dataset-ad17798fcea64e26ba91604fca520090 | 1993-01-01T00:10:00 | true | To a cooled (0° C.) mixture of NaBH4 (2.15 g, 0.057 mol) and isopropanol (70 mL) was added N-acetyl-4-piperidone (8.00 g, 0.057 mol). The mixture was allowed to warm to room temperature and stirred for 16 hours. CO2 was bubbled into the reaction mixture, EtOAc (120 mL) was added, and the precipitate was removed by filt... | CC(=O)N1CCC(O)CC1 | null | CC(=O)N1CCC(=O)CC1 | null | null | [BH4-].[Na+].[C:3]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4]>C(O)(C)C>[C:3]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4] | 16 | CC(C)O | null | null | 25 | 98 | null |
531,618 | 160,816 | [Na+] | [OH-] | null | null | ord_dataset-e402405fd21e4770a14f157cb62ca439 | 1987-01-01T00:07:00 | true | The compound of Example 28 (37.5 g, 0.10 mole) was suspended in 1,000 ml of ethanol and treated with 1N NaOH (100 ml, 0.10 mole). The mixture was warmed and stirred until clear; the ethanol and water were evaporated at reduced pressure to give 39.6 g of the white solid sodium 2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3... | Cc1c(-c2ccc(-c3ccccc3F)cc2)nc2ccc(F)cc2c1C(=O)[O-] | null | Cc1c(-c2ccc(-c3ccccc3F)cc2)nc2ccc(F)cc2c1C(=O)O | null | null | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]([CH3:24])=[C:22]([C:25]([OH:27])=[O:26])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:28])[CH:20]=3)[N:15]=2)=[CH:10][CH:9]=1.[OH-].[Na+:30]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]([CH3:24... | null | CCO | null | null | null | null | 99.7 |
549,758 | 289,958 | null | null | null | null | ord_dataset-5fb693db3950403e9ce1a516570153bf | 1994-01-01T00:05:00 | true | After 1 g (2.7 mmols) of 5'-O-acetyl-3'-deoxy-3'-bromoadenosine was added to 10 ml of pyridine, 418 mg (1.1 eq.) of benzoyl chloride was added to the mixture. The mixture was stirred at room temperature for 2 hours and pyridine was distilled off under reduced pressure. The residue was added to 30 ml of water followed b... | CC(=O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](OC(=O)c2ccccc2)[C@@H]1Br | null | O=C(Cl)c1ccccc1 | CC(=O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1Br | null | [C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:21])[C@@H:7]1[Br:22])(=[O:3])[CH3:2].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[C:23]([O:21][C@@H:8]1[C@H:7]([Br:22])[C@@H:6]([CH2:5][O:4][C:1](=[O:3])[CH3:... | 2 | c1ccncc1 | null | null | 25 | null | 91.8 |
851,990 | 118,324 | C[O-] | [Na+] | [Na] | null | ord_dataset-7a32ed4947a84db9890d8863ca9e55fb | 1984-01-01T00:06:00 | true | Slices of metal sodium (17.4 g, 0.755 mol) were added in small portions to methyl alcohol (250 ml) agitated at room temperature, to prepare sodium methoxide. After metal sodium pieces disappeared, a solution obtained by dissolving compound (C) (200.0 g, 0.581 mol) previously obtained, in dry toluene (600 ml) was gradua... | COC[C@H]1CC[C@H](c2ccccc2)CC1 | null | Cc1ccccc1 | CO | null | [Na].[CH3:2][OH:3].C[O-].[Na+].O.[C:8]1([CH3:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH3:2][O:3][CH2:14][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:10][CH2:9]1 | null | O | null | null | 25 | null | null |
87,996 | 553,483 | C[O-] | O=C([O-])O | [Na+] | null | ord_dataset-ec9decb576c4424c9685993f6262bd9c | 2002-01-01T00:07:00 | true | (S)-2,3-Dihydroxy-1-propylcarbamate benzyl ester (2.11 g, 0.01 mol) in 100 ml flask was dissolved in CHCl3 (30 ml). 1-Chlorocarbonyl-1-methylethylacetate (1.8 ml, 0.013 mol) was added and stirred for 3 hours at ambient temperature. Sat. aqueous solution of NaHCO3 (20 ml) was added and extracted three times with ethyl a... | O=C(NC[C@H]1CO1)OCc1ccccc1 | null | O=C(NC[C@H](O)CO)OCc1ccccc1 | null | null | [CH2:1]([O:8][C:9](=[O:16])[NH:10][CH2:11][C@H:12]([OH:15])[CH2:13]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].C[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:16])[NH:10][CH2:11][C@@H:12]1[O:15][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | 3 | ClC(Cl)Cl | null | null | 25 | 90 | null |
367,426 | 611,395 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-5c4ee54447b84205a10f9c0473172972 | 2003-01-01T00:10:00 | true | A mixture of 4-chloro-7-methoxy-N-(3-morpholinopropyl)quinoline-6-carboxamide (0.154 g), 4-phenoxyphenol (0.11 g), potassium carbonate (0.207 g) and DMF (4 ml) was stirred and heated to 100° C. for 16 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The aqueous phase wa... | COc1cc2nccc(Oc3ccc(Oc4ccccc4)cc3)c2cc1C(=O)NCCCN1CCOCC1 | null | Oc1ccc(Oc2ccccc2)cc1 | COc1cc2nccc(Cl)c2cc1C(=O)NCCCN1CCOCC1 | null | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:24][CH3:25])=[C:9]([C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[O:26]([C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=... | null | CN(C)C=O | null | null | 100 | null | 59.8 |
249,342 | 1,169,797 | null | null | null | null | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | 2012-01-01T00:05:00 | true | The title compound was prepared from 2-(4-bromo-imidazol-1-yl)-4-difluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (example E.7) (0.21 g, 0.5 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.14 g, 0.64 mmol) according to the general procedure VI. Obtained as a yel... | Nc1ccc(-c2cn(-c3nc(-c4ccc(C(F)(F)F)cc4)cc(C(F)F)n3)cn2)cn1 | null | FC(F)c1cc(-c2ccc(C(F)(F)F)cc2)nc(-n2cnc(Br)c2)n1 | CC1(C)OB(c2ccc(N)nc2)OC1(C)C | null | Br[C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:12]=[C:11]([CH:13]([F:15])[F:14])[CH:10]=[C:9]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[N:8]=2)[CH:6]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1>>[F:14][CH:13]([F:15])[C:11]1[CH:10]=[C:9]([C:16]2[CH:21]=[CH:20][C:19]... | null | null | null | null | null | null | null |
272,373 | 1,624,021 | null | null | null | null | ord_dataset-35c51552812941cda45194a013d34bb9 | 2015-01-01T00:08:00 | true | Methanesulphonyl chloride (6.29 g) was added dropwise to a solution of 6-(4-(3-hydroxypropoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]-pyridine-4-carbonitrile (10.34 g) and diisopropylethylamine (22.7 ml) in DCM (300 ml) at 0° C. The mixture was stirred at room temperature for 2 hours. The DCM was... | Cn1nnc2c(C#N)cc(-c3ccc(OCCCOS(C)(=O)=O)c(C(F)(F)F)c3)cc21 | null | CS(=O)(=O)Cl | Cn1nnc2c(C#N)nc(-c3ccc(OCCCO)c(C(F)(F)F)c3)cc21 | CCN(C(C)C)C(C)C | [CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2N=[C:21]([C:23]#[N:24])[C:20]3[N:25]=[N:26][N:27]([CH3:28])[C:19]=3[CH:18]=2)=[CH:13][C:12]=1[C:29]([F:32])([F:31])[F:30].[CH:33](N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15... | 2 | ClCCl | null | null | 25 | null | null |
169,601 | 1,279,155 | null | null | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | Following a procedure analogous to the procedure described in example 300 using N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide (110 mg, 0.211 mmol), isobutylamine (77 mg, 1.056 mmol) in 1,4-dioxane (2 mL), the title compound was obtained as a yellow fo... | CC(C)CNc1nccc(-c2sc(C3CCOCC3)nc2-c2cccc(NS(=O)(=O)c3ccoc3)c2F)n1 | null | CC(C)CN | O=S(=O)(Nc1cccc(-c2nc(C3CCOCC3)sc2-c2ccnc(Cl)n2)c1F)c1ccoc1 | null | Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:10][C:9]=2[C:19]2[C:20]([F:34])=[C:21]([NH:25][S:26]([C:29]3[CH:33]=[CH:32][O:31][CH:30]=3)(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=2)[CH:5]=[CH:4][N:3]=1.[CH2:35]([NH2:39])[CH:36]([CH3:38])[CH3:37]>O1CCOCC1>[F:34][C:20]1[C:19]([C... | null | C1COCCO1 | null | null | null | null | null |
117,959 | 987,261 | null | null | null | null | ord_dataset-35b56288528641309a040cc2b6710b61 | 2010-01-01T00:08:00 | true | N-(1-Methylpiperidin-4-yl)-2-phenylbenzoxazole-7-carboxamide was prepared from 2-phenylbenzoxazole-7-carboxylic acid and 4-amino-1-methylpiperidine using the method outlined in Step C of Example 7. This compound was obtained in 58% yield and obtained as a white solid: mp 209-210° C.; 1H NMR (300 MHz, CDCl3) δ 8.22 (m, ... | CN1CCC(NC(=O)c2cccc3nc(-c4ccccc4)oc23)CC1 | null | O=C(O)c1cccc2nc(-c3ccccc3)oc12 | CN1CCC(N)CC1 | null | [C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1>>[CH3:26][N:23]1[CH2:24][CH2:25][CH:20]([NH:19][C:16]([C:15]2[C:9]3[O:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:1... | null | null | null | null | null | 58 | null |
580,380 | 1,445,449 | null | null | null | null | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | 2014-01-01T00:07:00 | true | The title compound (40 mg, 67%) was synthesized as an orange solid according to the method described for Example A67 (oil temp 75° C., reflux 30 min) using 5-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (33.7 mg, 0.2 mmol) and 1H-indazole-6-carbaldehyde (29.2 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.56 (s, 1H), 10.90... | O=C1Nc2ccc(Cl)nc2/C1=C\c1ccc2cn[nH]c2c1 | null | O=Cc1ccc2cn[nH]c2c1 | O=C1Cc2nc(Cl)ccc2N1 | null | [Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=O)[CH:19]=2)[CH:14]=[N:13]1>>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18](/[CH:21]=[C:8]3/[C:9](=[O:11])[NH:10][C:5]4[C:6]/3=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[CH:19]=2)[CH:14]=[N:13]1 | null | null | null | null | null | 67.4 | null |
710,981 | 1,021,671 | [Pd] | null | null | null | ord_dataset-136cfada6ce247b4919085a57363459e | 2011-01-01T00:01:00 | true | 100 mg (18% by mass) of 10% palladium-on-charcoal are added to a solution of 560 mg (1.88 mmol, 1 eq) of methyl (E)-3-(2-methoxy-3′-methylaminobiphenyl-4-yl)acrylate in 10 ml of methanol. The reaction mixture is stirred at room temperature under a hydrogen atmosphere for 4 hours. The reaction medium is filtered through... | CNc1cccc(-c2ccc(CCC(=O)OC)cc2OC)c1 | null | CNc1cccc(-c2ccc(/C=C/C(=O)OC)cc2OC)c1 | null | null | [CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH:16]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH... | 4 | CO | null | null | 25 | 88 | null |
379,247 | 1,412,219 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | 2014-01-01T00:04:00 | true | To a solution of 3-chloro-4-(trifluoromethyl)phenol (Preparation 16, 100 mg, 0.470 mmol) in DMSO (1 mL) was added potassium carbonate (0.84 mg, 0.611 mmol) and the mixture stirred for 5 minutes. 4-methylphenyl-5-chloro-2,4-difluorobenzoate (Preparation 10, 0.133 mg, 0.470 mmol) was then added and the reaction stirred u... | Cc1ccc(OC(=O)c2cc(Cl)c(Oc3ccc(C(F)(F)F)c(Cl)c3)cc2F)cc1 | null | Oc1ccc(C(F)(F)F)c(Cl)c1 | Cc1ccc(-c2c(F)c(Cl)cc(C(=O)[O-])c2F)cc1 | null | [Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(=O)([O-])[O-].[K+].[K+].CC1C=CC([C:26]2[C:27]([F:37])=[C:28]([CH:32]=[C:33]([Cl:36])[C:34]=2F)[C:29]([O-:31])=[O:30])=CC=1>CS(C)=O>[Cl:36][C:33]1[C:34]([O:12][C:4]2[CH:5]=[CH:6][C:7]([C:8]([F:10])([F:11])[F:9])=[C:2]([Cl:1])[CH:3]=2)=[CH:... | 0.08 | CS(C)=O | null | null | null | null | 92.7 |
479,171 | 563,580 | O=C([O-])[O-] | [Na+] | null | null | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | 2002-01-01T00:09:00 | true | An ethanolic solution of 2-bromo-5-chloro-6-methylthio-1-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.047 g, 0.09 mmol) was deprotected in a modification of General Procedure VI with 0.036 g (0.34 mmol) of sodium carbonate in 0.5 ml of water. After stirring 1 h at ambient temperature, the mixture was t... | CSc1cc2c(cc1Cl)nc(Br)n2[C@@H]1OC[C@@H](O)[C@@H](O)[C@H]1O | null | CSc1cc2c(cc1Cl)nc(Br)n2[C@@H]1OC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O | null | null | [Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@@H:18]([O:19]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[C:26]([S:30][CH3:31])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@@H:18]([OH:19])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[C:... | 1 | O | null | null | 25 | 100 | null |
821,498 | 1,516,313 | [Na+] | null | null | null | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | 2014-01-01T00:12:00 | true | To a solution of 10-chloro-1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-amine (29 mg, 0.075 mmol) in methanol (5.0 mL) and acetic acid (1.0 mL) was added acetaldehyde (0.05 mL, 0.84 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was adde... | CCc1c(CC)c(N)c2c(nc3n2CCCCN3c2ccc(Cl)cc2Cl)c1Cl | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | CC=O | Nc1ccc(Cl)c2nc3n(c12)CCCCN3c1ccc(Cl)cc1Cl | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[CH2:12][CH2:13][CH2:14][CH2:15][N:7]21.[CH:25](=O)[CH3:26].[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:29].[Na+]>CO.C(O)(=O)C>[Cl:1][C:2]1[C:3]([CH2:25][CH3:26])=[C:4]([CH2:28][CH3:29])[C:5... | 5 | CC(=O)O | CO | null | 25 | 24 | null |
172,715 | 829,409 | null | null | null | null | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | 2008-01-01T00:07:00 | true | tert-Butyl {[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]sulfonyl}acetate (0.10 g, 0.24 mmol) was dissolved in trifluoroacetic acid (5 ml), and the mixture was stirred f or 0.5 hr. Diisopropyl ether was added to the mixture. The obtained precipitates were recrystallized from ethanol to give the titled compound (0.048 ... | O=C(O)CS(=O)(=O)c1cccc(-c2nc(=O)c3ccccc3s2)n1 | null | CC(C)(C)OC(=O)CS(=O)(=O)c1cccc(-c2nc(=O)c3ccccc3s2)n1 | null | null | [O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([S:18]([CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])(=[O:20])=[O:19])[CH:15]=[CH:14][CH:13]=2)=[N:3]1.C(OC(C)C)(C)C>FC(F)(F)C(O)=O>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([S:18]([CH2:21][C:22]([OH:... | 0.5 | CC(C)OC(C)C | O=C(O)C(F)(F)F | null | null | null | 55.2 |
293,709 | 1,391,926 | N | null | null | null | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | 2014-01-01T00:02:00 | true | 30% Aqueous NH3 solution (250 μL) and 35% aqueous H2O2 solution (83 μl) are added at 0° C. to a solution of 2-((S)-6-((R)-4-(4-cyano-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid (19 mg) in ethanol (2 mL). The mixture is stirred at room temperature for 12 hours, while... | Cc1cc(C(N)=O)cc(C)c1-c1ccc(F)c2c1CC[C@H]2Oc1ccc2c(c1)OC[C@H]2CC(=O)O | null | Cc1cc(C#N)cc(C)c1-c1ccc(F)c2c1CC[C@H]2Oc1ccc2c(c1)OC[C@H]2CC(=O)O | OO | null | N.[OH:2]O.[C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]3[C:14]=2[CH2:15][CH2:16][C@H:17]3[O:23][C:24]2[CH:36]=[CH:35][C:27]3[C@H:28]([CH2:31][C:32]([OH:34])=[O:33])[CH2:29][O:30][C:26]=3[CH:25]=2)=[C:8]([CH3:37])[CH:7]=1)#[N:5]>C(O)C>[C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:1... | 12 | CCO | null | null | 25 | null | null |
201,976 | 1,647,584 | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 | null | null | null | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | 2015-01-01T00:10:00 | true | See FIG. 16(b). 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (200 mg, 0.67 mmol) was taken in DCM (10 mL). Added 1-Propanephosphonic acid cyclic anhydride (427 mg, 1.34 mmol) followed by the addition of Triethyl amine (339 mg, 3.35 mmol) and cyclopropylmethanamine (95 mg, 1.3... | COc1ncnc(Cn2cc(C(=O)NCC3CC3)c3ncccc32)c1C | null | NCC1CC1 | COc1ncnc(Cn2cc(C(=O)O)c3ncccc32)c1C | null | [CH3:1][O:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([OH:21])=O)=[CH:11]2)[C:4]=1[CH3:22].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(N(CC)CC)C.[CH:48]1([CH2:51][NH2:52])[CH2:50][CH2:49]1>C(Cl)Cl.O>[CH:48]1([CH2:51][NH:52][C:19]([C:12]2[C:13]3=[N:14][CH:15]=[CH:16]... | 8 | ClCCl | O | CCN(CC)CC | 25 | null | 74 |
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