original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
423,573 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([NH:14]C(=O)C)[C:3]=1[C:4]([OH:6])=[O:5].Cl>[OH-].[Na+]>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([NH2:14])[C:3]=1[C:4]([OH:6])=[O:5] | CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 95 | 1 | 450 ml of 2N NaOH are initially taken and 75.6 g (0.317 mol) of 2-methyl-3-nitro-6-acetamidobenzoic acid are added. The reaction mixture is then warmed to 95° C. and is stirred at this temperature for one hour. After cooling to 10° C., it is acidified by addition of 425 ml of 2N HCl, and the precipitate which deposits ... | Cc1c([N+](=O)[O-])ccc(N)c1C(=O)O | null | null | null |
697,199 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | C(O)(=O)C.[C:5]1([CH3:20])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[C:13]1[C:14]([CH3:19])=[N:15][NH:16][C:17]=1[NH2:18].[C:21]([CH:24]([C:30](OCC)=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])(=O)[CH3:22]>C1(C)C(C)=CC=CC=1>[C:5]1([CH3:20])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[C:13]1[C:14]([CH... | CCOC(=O)C(C(C)=O)C(=O)OCC | Cc1cc(C)c(-c2c(C)n[nH]c2N)c(C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | Acetic acid (5 mL) was added to a solution of 4-mesityl-3-methyl-1H-5-pyrazoleamine (5 g, 23.22 mmol) and diethyl 2-acetylmalonate (4.7 g, 23.22 mmol) in xylene (40 mL), followed by heating under reflux for seven hours. The reaction mixture was evaporated as it was, and water was added thereto. After extracting with et... | CCOC(=O)c1c(C)[nH]c2c(-c3c(C)cc(C)cc3C)c(C)nn2c1=O | null | 36.6 | null |
74,766 | ord_dataset-b9d8ddf9c2884d40859b6b5f24815a7d | null | 1980-01-01T00:12:00 | true | [NH2:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]1=O.C(O[C:18](=[NH:27])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)C>>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3]1=[N:27][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)=[N:1... | COc1ccc2c(c1)CCN(N)C2=O | CCOC(=N)c1cccc(OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The compound is prepared according to the procedure of Example 1 from 2-amino-6-methoxy-3,4-dihydro-1(2H)-isoquinolinone (prepared according to the procedure described in Belgian Pat. No. 780,885; m.p. 101°-3° C.) and m-methoxybenzimidic acid ethyl ester; m.p. 132°-3° C. | COc1cccc(-c2nc3n(n2)CCc2cc(OC)ccc2-3)c1 | null | null | null |
49,310 | ord_dataset-0bb2e99daa66408fb8dbd6a0781d241c | null | 1978-01-01T00:12:00 | true | [O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH3:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([CH3:19])=[CH:13][C:10]=1[CH:11]=O>CCO.Cl>[CH3:18][O:17][C:15]1[C:14]([CH3:19])=[CH:13][C:10]([CH:11]=[C:3]2[C:4](=[O:7])[C:5](=[CH:11][C:10]3[CH:13]=[C:14]([CH3:19])[C:15]([O:17][CH3:18])=[CH:16][C:9]=3[CH3:8])[CH2:6][O:... | COc1cc(C)c(C=O)cc1C | O=C1CCOCC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 24 | A solution of 7.0 g (0.07 mole) of tetrahydro-4H-pyran-4-one and 25.2 g (0.15 mole) of 2,5-dimethyl-p-anisaldehyde in 75 ml of EtOH and 10 ml of concentrated HCl is stirred and heated at reflux for 3 hours. The resulting mixture is kept at room temperature for 24 hours, yielding 10.7 g (39%) of yellow solid, m.p. 182°-... | COc1cc(C)c(C=C2COCC(=Cc3cc(C)c(OC)cc3C)C2=O)cc1C | null | 38.9 | null |
448,499 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | CCOC(/N=N/C(OCC)=O)=O.[F:13][C@H:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][OH:16].[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:27]=[CH:26][C:25]=1[C:36]1[N:41]=[CH:40][C:39](O)=[CH:38][N:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:23][C:24]1[C:29]([F:30... | CCCCCC[C@@H](F)CO | CCCCCc1ccc(-c2ncc(O)cn2)c(F)c1F | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | --DEAD (470 mg, 2.70 mmol) in THF (3 ml) was added dropwise via syringe to a stirring solution of (R)-(+)-2-fluorooctanol (396 mg, 2.70 mmol), the hydroxypyrimidine 33 (750 mg, 2.70 mmol) and triphenylphosphine (707 mg, 2.70 mmol) in THF (10 ml) under nitrogen at ambient temperature for 15 h. The solvent was removed in... | CCCCCC[C@@H](F)COc1cnc(-c2ccc(CCCCC)c(F)c2F)nc1 | null | 55.3 | null |
783,031 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:14]1([S:20][CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:21][S:20][C:14]1[CH:19]=[CH:18][C:17]([C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[O:13])=[CH:16][CH:15]=1 | O=C(O)c1cccc2ccccc12 | CSc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of 1-naphthoic acid (10 g, 58.08 mmol), thioanisol (8.19 ml, 69.7 mmol) and polyphosphoric acid (100 g) was heated for 12 hours on water bath at 80° C. Reaction mixture was poured onto ice water and extracted with ethylacetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and c... | CSc1ccc(C(=O)c2cccc3ccccc23)cc1 | null | null | null |
916,065 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | C(OC([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:26])[NH:15][C@@:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][C@@H:17]1[CH:19]=[CH2:20])=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH2:24]([O:23][C:21]([C@:16]1([NH:15][C:14]([C@@H:9]2[CH2:10][C@@H:11]([OH:13])[CH2:12][NH:8]2)=[O:26])[CH2:18][C@@H:17]1[CH:19]=[... | C=C[C@H]1C[C@@]1(NC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C)C(=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | Compound 90 was kept in 30% trifluoroacetic acid in dichloromethane and 1% MeOH for 2 hrs before it was concentrated to dryness. The residue was re-dissolved In dichloromethane and during stirring 1N NaOH was added to pH 10-11. The organic layer was separated and concentrated which gave 1.6 g of the title product. HPLC... | C=C[C@H]1C[C@@]1(NC(=O)[C@@H]1C[C@@H](O)CN1)C(=O)OCC | null | null | null |
1,754,141 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH:1]1([C:4]2[C:5]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:6][C:7]([C:10]([NH:12][C:13]([C:20]3[N:24]=[C:23]([CH3:25])[O:22][N:21]=3)([CH3:19])[C:14](OCC)=[O:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.CO.[NH3:34]>>[NH2:34][C:14](=[O:15])[C:13]([NH:12][C:10]([C:7]1[CH:6]=[C:5]([O:26][CH2:27][C:28]([F:31])([F:30... | N | CCOC(=O)C(C)(NC(=O)c1cc(OCC(F)(F)F)c(C2CC2)cn1)c1noc(C)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of ethyl 2-[[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonyl]amino]-2-(5-methyl-1,2,4-oxadiazol-3-yl)propanoate (example 147b, 0.05 g, 113 μmol) in ammonia 7N in MeOH (1.00 ml, 7.01 mmol) was stirred at room temperature overnight. Volatiles were removed in vacuo and the crude material was purified... | Cc1nc(C(C)(NC(=O)c2cc(OCC(F)(F)F)c(C3CC3)cn2)C(N)=O)no1 | null | 69 | null |
1,198,818 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:17]#[N:18])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:20][NH2:21]>C(O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:17]([NH:20][NH2:21])=[NH:18])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | NN | Cc1cc(C#N)sc1C(=O)NCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of N-benzyl-5-cyano-3-methylthiophene-2-carboxamide (0.80 g, 3.12 mmol) and hydrazine monohydrate (8.00 mL, 164.9 mmol) in ethanol was stirred at reflux for 18 h. The reaction mixture was allowed to cool to ambient temperature, and concentrated in vacuo. The residue was triturated with ethyl acetate to afford... | Cc1cc(C(=N)NN)sc1C(=O)NCc1ccccc1 | null | 72.2 | null |
907,413 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | C([O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:23])[C:10]3[C:15]([O:16][C:17]=2[C:18]=1[O:19][CH2:20][CH:21]=[CH2:22])=[CH:14][CH:13]=[CH:12][CH:11]=3)C=C.[C:24]1(OC2C=CC=CC=2)[CH:29]=CC=C[CH:25]=1>>[CH2:29]([C:18]12[C:5](=[O:4])[CH:6]3[CH:7]=[C:8]4[C:17]1([CH:21]([CH2:22]3)[CH2:20][O:19]2)[O:16][C:15]1[CH:14]=[CH:13][CH:12... | C=CCOc1ccc2c(=O)c3ccccc3oc2c1OCC=C | c1ccc(Oc2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | A stirred solution of 3,4-bis-allyloxy-xanthen-9-one (236.4 mg, 0.767 mmol) and diphenyl ether (3.0 mL) was refluxed in an oil bath at 190° C. for 11 h. The solution was cooled to room temperature and product was purified twice by flash column chromatography (dichloromethane) to yield 28.0 mg (12%) of the title compoun... | C=CCC12OCC3CC(C=C4C(=O)c5ccccc5OC431)C2=O | null | 12 | null |
1,636,634 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[CH2:14][CH:13]2[CH:10]([CH2:11][NH:12]2)[CH2:9]1)=[O:7].Br[C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=1>>[CH2:28]([O:27][C:25](=[O:26])[C:24]1[CH:30]=[CH:31][C:21]([N:12]2[CH2:11][CH:10]3[CH:13]2[CH... | O=C(NCc1ccc(Cl)cc1Cl)N1CC2CNC2C1 | CCOC(=O)c1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the experimental procedure of example 20) rac-3-(2,4-Dichloro-benzylcarbamoyl)-3,6-diaza-bicyclo[3.2.0]heptane using ethyl 4-bromobenzoate instead of 2-bromopyrimidine was converted into the title compound which was obtained as a white solid and directly used without further purification. | CCOC(=O)c1ccc(N2CC3CN(C(=O)NCc4ccc(Cl)cc4Cl)CC32)cc1 | null | null | null |
102,965 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][C:28]2[N:29]=[C:30]([CH3:33])[S:31][CH:32]=2)[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.[ClH:34]>CO>[ClH:34].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][C:28]2[N:... | Cc1nc(CON=C(C(=O)NC2C(=O)N3C(C(=O)O)=CCS[C@H]23)c2csc(NC=O)n2)cs1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 6.5 | A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-methylthiazol-4-ylmethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 240 mg.) and conc. hydrochloric acid (71 mg.) in methanol (2.5 ml.) was stirred at room temperature for 6.5 hours. After removing the solvent from the resultant solution in vacuo, the resid... | Cc1nc(CON=C(C(=O)NC2C(=O)N3C(C(=O)O)=CCS[C@H]23)c2csc(N)n2)cs1 | null | 96.7 | null |
1,448,956 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([C:8]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH:11]([CH3:13])[N:10]([CH3:14])[C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[C:27]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>ClCCl>[Si:31]([O:1][C:2]1[CH:3]=[C:4]([C:8]2([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21... | CC1CC(c2ccccc2)(c2cccc(O)c2)C(=O)N1C | CC(C)(C)[Si](C)(C)Cl | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 16 | Product of Step 6 (4.9 g) was dissolved in dichloromethane (200 mL). To this, imidazole (5 g) and tertiarybutyldimethylsilyl chloride (5 g) was added. The reaction mixture was stirred at 25° C. for 16 hrs. Then, the reaction mixture was extracted with water (200 mL) and the organic layer was dried on anhydrous magnesiu... | CC1CC(c2ccccc2)(c2cccc(O[Si](C)(C)C(C)(C)C)c2)C(=O)N1C | null | null | null |
450,370 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | [CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][N+:15]([O-])=[C:14]([CH3:19])[C:13]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:24]C(=O)C)(=[O:23])[CH3:22]>>[C:21]([O:24][CH2:19][C:14]1[C:13]([CH3:20])=[C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:17]=[CH... | CC(=O)OC(C)=O | Cc1c(OCCOCc2ccccc2)cc[n+]([O-])c1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 85 | 1 | A mixture comprising 6.5 g of 4-(2-benzyloxyethoxy-2,3-dimethylpyridine N-oxide and 56 ml of acetic anhydride was stirred at 80 to 90° C. for one hour and distilled to remove the acetic anhydride. The obtained residue was made weakly basic with an aqueous solution of sodium carbonate and extracted with methyl ethyl ket... | CC(=O)OCc1nccc(OCCOCc2ccccc2)c1C | null | null | null |
1,240,955 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [C:1]([C:3]1[S:7][C:6]([O:8][C:9]2[CH:10]=[C:11]([CH3:25])[C:12]3[CH:16]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:15][B:14]([OH:23])[C:13]=3[CH:24]=2)=[N:5][N:4]=1)#[N:2].Cl.[NH2:27][OH:28].C(N(CC)CC)C>CO>[OH:23][B:14]1[C:13]2[CH:24]=[C:9]([O:8][C:6]3[S:7][C:3]([C:1](=[NH:2])[NH:27][OH:28])=[N:4][N:5]=3)[CH:10]... | NO | CCOC(=O)CC1OB(O)c2cc(Oc3nnc(C#N)s3)cc(C)c21 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CO | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of ethyl 2-(6-(5-cyano-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (1.63 g, 4.54 mmol, 1 eq.) and hydroxylamine hydrochloride (0.79 g, 11.35 mmol, 2.5 eq.) in methanol was added triethylamine (2.22 ml, 15.88 mmol, 3.5 eq.). After stirring at room temperature ... | CCOC(=O)CC1OB(O)c2cc(Oc3nnc(C(=N)NO)s3)cc(C)c21 | null | 97.2 | null |
938,350 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [Cl:1][C:2]1[N:3]=[C:4]([O:9][CH3:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[S:19](Cl)(=[O:21])=[O:20]>>[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[S:19]([NH:8][C:5]1[C:4]([O:9][CH3:10])=[N:3][C:2]([Cl:1])=[CH:7][N:6]=1)(=[O:21])=[O:20] | O=S(=O)(Cl)c1cccc(Cl)c1Cl | COc1nc(Cl)cnc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by the method of Example I (reaction performed at room temperature) using 5-chloro-3-methoxy-2-pyrazinamine (0.1 g) and 2,3-dichlorobenzenesulphonyl chloride (0.15 g). Yield 0.05 g. | COc1nc(Cl)cnc1NS(=O)(=O)c1cccc(Cl)c1Cl | null | null | null |
1,104,709 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [N:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:14][C:15]#[N:16]>>[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:14][C:15]#[N:16])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | C1CCN(C2CCNCC2)CC1 | N#CCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is synthesized by coupling of [1,4′]Bipiperidinyl (commercially available from Fluorochem Ltd) and bromoacetonitrile analogously to the preparation of Intermediate 149.2 as a colorless oil; ES-MS: M+=208.2. | N#CCN1CCC(N2CCCCC2)CC1 | null | null | null |
1,460,252 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl.[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C@@H:16]([CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[O:18]>>[CH2:36]([... | N[C@@H](COCc1ccccc1)C(=O)Nc1ccc(Oc2ccc(F)cc2)cc1 | O=C(O)CCCCc1ccccc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Proceeding as in Example 1, but substituting 5-phenylpentanoic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 104, (S)—N-(3-(benzyloxy)-1-(4-(4-fluorophenoxy)phenylamino)-1-oxopropan-2-yl)-5-phenylpentanamide (3 mg, 46.2%). | O=C(CCCCc1ccccc1)N[C@@H](COCc1ccccc1)C(=O)Nc1ccc(Oc2ccc(F)cc2)cc1 | null | 46.2 | null |
355,360 | ord_dataset-930bf31b476c482e8ba87824089eb600 | null | 1997-01-01T00:02:00 | true | N.[F:2][C:3]1[N:4]=[C:5]([NH2:30])[C:6]2[N:7]=[CH:8][N:9]([C:28]=2[N:29]=1)[C@@H:10]1[O:27][C@H:21]([CH2:22][O:23]C(=O)C)[C@@H:16]([O:17]C(=O)C)[C@H:11]1[O:12]C(=O)C>C(O)C>[F:2][C:3]1[N:4]=[C:5]([NH2:30])[C:6]2[N:7]=[CH:8][N:9]([C:28]=2[N:29]=1)[C@@H:10]1[O:27][C@H:21]([CH2:22][OH:23])[C@@H:16]([OH:17])[C@H:11]1[OH:12] | CC(=O)OC[C@H]1O[C@@H](n2cnc3c(N)nc(F)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Anhydrous ammonia was bubbled through a magnetically stirred suspension of 2-fluoro-2',3',5'-tri-O-acetyl-adenosine (2.10 g, 5.1 mmol) in absolute ethanol (500 mL) cooled in an ice-water bath. After 30 min the mixture became homogenous so the addition of ammonia was stopped. The container was tightly stoppered and was ... | Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | null | 90.7 | null |
1,467,965 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[N:12][N:13]([CH2:15][CH2:16][C@@:17]([CH3:32])([S:28]([CH3:31])(=[O:30])=[O:29])[C:18]([NH:20][O:21]C2CCCCO2)=[O:19])[CH:14]=1.Cl>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[N:12][N:13]([CH2:15][CH2:16][C@@:17]([CH... | COc1ccc(-c2cn(CC[C@](C)(C(=O)NOC3CCCCO3)S(C)(=O)=O)nn2)c(Cl)c1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 2-chloro-1-ethynyl-4-methoxybenzene (15 mg, 0.093 mmol, 1 eq) and (2R)-4-azido-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (30 mg 0.093 mmol, 1 eq) in EtOH—H2O (7 mL:1 mL) was added sodium ascorbate (19 mg, 0.093 mmol, 1 eq) and CuSO4 (9 mg, 0.037 mmol, 0.4 eq). The reaction m... | COc1ccc(-c2cn(CC[C@](C)(C(=O)NO)S(C)(=O)=O)nn2)c(Cl)c1 | null | 67.1 | null |
781,501 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1.CCOCC>CCCCCC>[Br:5][C:6]1[CH:11]=[C:10]([N+:1]([O-:4])=[O:2])[C:9]([OH:12])=[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1 | CC(C)(C)c1cc(Br)ccc1O | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CCCCCC | null | null | null | null | null | null | null | null | null | null | 2 | Concentrated nitric acid (112 ml) was gradually added dropwise to a solution of 4-bromo-2-(tert-butyl)phenol (485 g) in hexane (3000 ml) while cooling on ice. After stirring for 2 hours at below 20° C., ether (2000 ml) was added and the reaction mixture was washed with water. The organic layer was dried over anhydrous ... | CC(C)(C)c1cc(Br)cc([N+](=O)[O-])c1O | null | null | null |
612,248 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | C([O:4][CH2:5][C:6]1[C:7]([CH3:33])=[C:8]([C:14]2([C:30]([NH2:32])=[O:31])[CH:18]([S:19](=[O:29])(=[O:28])[NH:20][C:21]3[O:25][N:24]=[C:23]([CH3:26])[C:22]=3[Cl:27])[CH:17]=[CH:16][S:15]2)[C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12])(=O)C.C[O-].[Na+]>CO>[OH:4][CH2:5][C:6]1[C:7]([CH3:33])=[C:8]([C:14]2([C:30]([NH2:32])=[O:31... | CC(=O)OCc1c(C)cc(C)c(C2(C(N)=O)SC=CC2S(=O)(=O)Nc2onc(C)c2Cl)c1C | null | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | A solution of 2-(3-acetoxymethyl-2,4,6-trimethylphenyl)-3-(4-chloro-3-methyl-5-isoxazolylsulfamoyl)-2-thiophenecarboxamide (Example 15) (250 mg, 0.49 mmol) in anh. MeOH (5 mL) was cooled to 0° C. and charged with 25% solution of sodium methoxide in MeOH (1.08 g, 5.0 mmol). Stirred for 30 min at 0° C. then the methanol ... | Cc1cc(C)c(C2(C(N)=O)SC=CC2S(=O)(=O)Nc2onc(C)c2Cl)c(C)c1CO | null | null | null |
1,233,414 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [Si:1]([O:18][CH2:19][CH2:20][N:21]([CH2:42][CH:43]([OH:65])[CH2:44]OC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:22][CH2:23][O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[... | CC(C)(C)[Si](OCCN(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)CC(O)COC(c1ccccc1)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1 | O=CO | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 20 | Another batch of XIII was prepared using the following procedure: to a solution of VIII (2.0 g, 2.23 mmol) in diethyl ether (3 mL) was added 85% formic acid (8.2 mL) and the resulting reaction mixture was stirred at room temperature. After 20 h, solid NaHCO3 was added portion wise to neutralize the acidic solution. The... | CC(O)C(O)N(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | 67 | null |
1,639,925 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([NH:20][C@@H:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@H:24]([O:31][CH2:32][C:33]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=O)[CH2:23][CH2:22]2)=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].B>C1COCC1.O>[C:... | Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)N[C@H]2CC[C@@H](OCC(=O)N3CCOCC3)c3ccccc32)cc1 | null | null | B | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 60 | 23 | To a solution of Intermediate 32d (50 mg, 62.3 μmol) in THF (1.7 mL) was added borane (1M in THF, 0.12 mL, 0.12 mmol) and the mixture stirred at 60° C. After 23 h, further borane (1M in THF, 0.31 mL, 0.31 mmol) was added. After 26 h, further borane (1M in THF, 0.31 mL, 0.31 mmol) was added. After 3 d, the cooled reacti... | Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)N[C@H]2CC[C@@H](OCCN3CCOCC3)c3ccccc32)cc1 | null | null | null |
1,250,613 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | C[O:2][C:3]([C:5]1[S:6][C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)=[CH:8][C:9]=1[N:10]([CH:20]([CH3:22])[CH3:21])[C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].O.[Li+].[OH-]>O1CCOCC1>[F:29][C:25]1[CH:24]=[C:23]([C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([N:10]([CH:20]... | COC(=O)c1sc(-c2cccc(F)c2)cc1N(C(=O)C1CCC(C)CC1)C(C)C | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 3 | 5-(3-Fluoro-phenyl)-3-[isopropyl-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (25 mg, 0.060 mmol) was dissolved in a 4:1 mixture of dioxane:H2O (0.8 mL) and then LiOH 1N (0.3 ml, 0.300 mmol) was added. After 3 hours of stirring at room temperature, solvents were removed and then partit... | CC1CCC(C(=O)N(c2cc(-c3cccc(F)c3)sc2C(=O)O)C(C)C)CC1 | null | 82.6 | null |
926,513 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=2)[CH:3]=1.[N:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>>[F:20][C:15]1[CH:14]=[C:13]([C:4]2[CH:3]=[C:2]([C:24]3[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9... | OB(O)c1ccncc1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared from 6b using 4-pyridinylboronic acid according to method P. Yellow powder; Yield: 20%; mp>350° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 7.02 (d, J=2.6 Hz, 1H), 7.07 (t, J=8.8 Hz, 1H), 7.34 (dd, J=9.0, 2.6 Hz, 1H), 7.64 (d, J=5.9 Hz, 2H), 7.93 (s, 1H), 7.95-8.00 (m, 2H), 8.08 (dd, J=13.0, 2.1 H... | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccncc3)c2c1 | null | 20 | null |
202,538 | ord_dataset-19e5fc80c1554f4f8641c835e055f02b | null | 1990-01-01T00:01:00 | true | [CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([O:22]CC1C=CC=CC=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]>C(O)C.[Ni]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([OH:22])[CH:14]=[CH:13][CH:1... | CCOC(=O)c1ncc2[nH]c3cccc(OCc4ccccc4)c3c2c1COC | null | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 10 g of 5-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is refluxed for 3 hours in 100 ml of ethanol with 4 g of Raney nickel. After the catalyst has been removed by filtration, the filtrate is concentrated under vacuum. The residue is chromatographed over silica gel with methylene chloride+ethano... | CCOC(=O)c1ncc2[nH]c3cccc(O)c3c2c1COC | null | 93.6 | null |
1,313,583 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[N:10]([CH2:21][C:22]([CH3:24])=[CH2:23])[C:9]1=[O:25])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:... | [H][H] | C=C(C)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C[C@@H](c2ccccc2)[C@H]1C | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of tert-butyl[(3S,5S,6R)-6-methyl-1-(2-methylprop-2-en-1-yl)-2-oxo-5-phenylpiperidin-3-yl]carbamate (0.129 g, 0.364 mmol) in ethanol (15 mL) was added 10 wt. % palladium on carbon (39 mg, 0.036 mmol) and the mixture was stirred under a balloon of hydrogen at 23° C. for 1 h. The catalyst was removed by fil... | CC(C)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C[C@@H](c2ccccc2)[C@H]1C | null | null | null |
670,537 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[C:18](=O)(O)[O-].[Na+]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:18])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1 | O=C([O-])O | O=C(O)c1ccc2c(c1)CCO2 | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred solution of 2,3-dihydrobenzofuran-5-carboxylic acid (3.96 g, 24.1 mmol) in MeOH (200 mL) is added concentrated sulfuric acid (0.5 mL). The mixture is heated to reflux for 24 h. The mixture is cooled to rt, followed by the addition of solid sodium bicarbonate. The reaction mixture is concentrated in vacuo, ... | COC(=O)c1ccc2c(c1)CCO2 | null | 98 | null |
1,756,826 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | S(=O)(=O)(O)O.[Si]([O:13][CH2:14][CH2:15][O:16][C:17]1[C:18]([NH:39][C:40]2[C:45]([C:46]#[N:47])=[CH:44][N:43]=[CH:42][CH:41]=2)=[N:19][C:20]([C:23]2[C:24]3[CH2:38][CH2:37][CH2:36][C:25]=3[N:26]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[N:27]=2)=[N:21][CH:22]=1)(C(C)(C)C)(C)C.C(=O)([O-])[OH:49].[Na+]... | O=C([O-])O | CC(C)(C)[Si](C)(C)OCCOc1cnc(-c2nn(Cc3ccccc3F)c3c2CCC3)nc1Nc1ccncc1C#N | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | 0.23 mL sulfuric acid (4.18 mmol, 25.0 eq.) were added to 98 mg of 4-({5-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]pyrimidin-4-yl}amino)nicotinonitrile 2-3-10 (0.167 mmol, 1.00 eq.). The reaction mixture was stirred at rt over night. Aqueous saturated s... | NC(=O)c1cnccc1Nc1nc(-c2nn(Cc3ccccc3F)c3c2CCC3)ncc1OCCO | null | null | null |
1,599,325 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | CS([O:5][CH2:6][C:7]1[C:8]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=[N:9][S:10][CH:11]=1)(=O)=O.[F:19][C:20]1[C:25]([F:26])=[C:24](O)[CH:23]=[CH:22][C:21]=1[CH2:28][CH2:29][C:30]([O:32]CC)=[O:31]>>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]2[C:7]([CH2:6][O:5][C:24]3[CH:23]=[CH:22][C:21]([CH2:28][CH2:29][C:... | CS(=O)(=O)OCc1csnc1-c1ccc(Br)cc1 | CCOC(=O)CCc1ccc(O)c(F)c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the procedure described in Example 91 following Step 5 and 6 by coupling (3-(4-bromophenyl)isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (400 MHz... | O=C(O)CCc1ccc(OCc2csnc2-c2ccc(Br)cc2)c(F)c1F | null | null | null |
182,206 | ord_dataset-f25e1b7f8ef54305a5170f5395a768c7 | null | 1989-01-01T00:01:00 | true | [C:1]([Cl:4])(Cl)=[S:2].[OH:5][C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[C:9]([O:11][Si:12]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:10].C(N(CC)CC)C>C(OCC)C>[Cl:4][C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[C:9]([... | S=C(Cl)Cl | CC(C)(C)[Si](OC(=O)c1cccc(O)c1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCOCC | null | null | null | null | null | null | null | null | null | -78 | 2 | To a stirred solution of 130 ml of thiophosgene in 250 ml of dry diethyl ether at -78° C. was added dropwise a mixture of 72 g of diphenyl- (2-methylprop-2-yl)silyl 3-hydroxybenzoate and 29 ml of triethylamine in 200 ml of dry diethyl ether. The mixture was stirred at -78° C. for 30 minutes, at room temperature for 120... | CC(C)(C)[Si](OC(=O)c1cccc(OC(=S)Cl)c1)(c1ccccc1)c1ccccc1 | null | null | null |
1,482,645 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.Cl>CO.O>[OH:17][C:13]1[CH:12]=[C:11]([NH:10][C:2]2[N:7]=[C:6]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)[C:5]([F:9])=[CH:4][N:3]=2)[CH:16]=[CH:15][CH:14]=1 | Nc1cccc(O)c1 | Fc1cnc(Cl)nc1Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 2,4-dichloro-5-fluoropyrimidine (0.0167 g, 0.1 mmol) and 3-aminophenol (0.033 g, 0.3 mmol) in MeOH: H2O (1.8:0.2 mL; v/v) was shaken in a sealed tube at 100° C. for 24 h (or 80° C. for 3 days), cooled to room temperature, diluted with water (15 mL), acidified with 2N HCl (pH>2). Upon saturation with sodium... | Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | null | null | null |
402,705 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[H][H]>[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:12][C:13]3[C:... | COc1ccc(-c2[nH]c3ccccc3c2CCNCCc2ccc([N+](=O)[O-])cc2)cc1OC | [H][H] | null | [Pd+2] | Cl | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred solution of [2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]ethyl]-[2-(4-nitrophenyl)ethyl]amine (45 mg in 4 mL methanol) was added 2N hydrochloric acid (0.020 mL) and 18 mg of 10% palladium hydroxide on carbon catalyst. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen... | COc1ccc(-c2[nH]c3ccccc3c2CCNCCc2ccc(N)cc2)cc1OC | null | 76.2 | null |
633,459 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | [CH2:1]([S:3]([C:6]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([OH:15])[C:8]=2[CH:7]=1)(=[O:5])=[O:4])[CH3:2].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:20][C@H:21]1[O:23][CH2:22]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([S:3]([C:6]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:20][C@H:21]3[O:23][CH2:22]3)[C:8]=2[CH:7]... | O=[N+]([O-])c1ccc(S(=O)(=O)OC[C@@H]2CO2)cc1 | CCS(=O)(=O)c1cc2c(O)cccc2o1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By the reactions in the same manner as in Starting Material Synthesis Example 1 using 2-(ethylsulfonyl)-4-hydroxybenzo(b)furan (2.75 g), (S)-glycidyl nosylate (3.48 g) and potassium carbonate (5.05 g), a crude product of the title compound (3.62 g) was obtained as a pale-yellow oil. | CCS(=O)(=O)c1cc2c(OC[C@@H]3CO3)cccc2o1 | null | 105.5 | null |
535,289 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[O:19])[CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([O:22][CH3:23])=[C:7]([O:20][CH3:21])[CH:8]=2)[N:3]=1.[CH3:24][NH2:25]>CO>[CH3:21][O:20][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:22][CH3:23])[N:3]=[C:2]([NH:25][CH3:24])[N:11]=[C:10]2[C:12]1[CH:17]=[CH:16][CH:1... | CN | COc1cc2nc(Cl)nc(-c3cccc(C=O)c3)c2cc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 1.50 g of 2-chloro-6,7-dimethoxy-4-(3-formylphenyl)quinazoline and 15 ml of 40% methylamine in methanol, 1.00 g of the title compound was obtained as yellow crystals in the same manner as in Production Example 8. | CNc1nc(-c2cccc(C=O)c2)c2cc(OC)c(OC)cc2n1 | null | null | null |
1,075,504 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [Mg].Br[C:3]1[CH:8]=[CH:7][C:6]2[O:9][CH2:10][O:11][C:5]=2[CH:4]=1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1)=O>O1CCCC1.BrBr>[Br:21][C:17]1[CH:16]=[C:15]([C:13]([C:3]2[CH:8]=[CH:7][C:6]3[O:9][CH2:10][O:11][C:5]=3[CH:4]=2)=[CH2:12])[CH:20]=[CH:19][CH:18]=1 | CC(=O)c1cccc(Br)c1 | Brc1ccc2c(c1)OCO2 | null | BrBr | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a mixture of magnesium turnings (440 mg, 0.01 mol, 1.2 eq) in dry tetrahydrofuran (5 mL), was added 4-bromo-1,2(methylendioxy)benzene (3.1 g, 0.01 mol, 1.1 eq) in dry tetrahydrofuran (10 mL) and bromine (0.5 mL). The resulting solution was refluxed for 2 hours. Then the mixture was cooled at room temperature and a s... | C=C(c1cccc(Br)c1)c1ccc2c(c1)OCO2 | null | null | null |
1,419,787 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH3:1][CH:2]([O:4][C:5](=[O:30])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](B3OC(C)(C)C(C)(C)O3)[CH:15]=2)[N:10]([C:26](=[O:28])[CH3:27])[C@@H:9]([CH3:29])[CH2:8]1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[C:38]1[CH:39]=[N:40][N:41]([CH2:43][CH2:44][N:45]([CH3:53])[CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]... | CN(CCn1cc(Br)cn1)Cc1ccccc1 | CC(=O)N1c2ccc(B3OC(C)(C)C(C)(C)O3)cc2[C@H](NC(=O)OC(C)C)C[C@@H]1C | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 90 | null | 1-Methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (300 mg, 0.721 mmol, for a preparation see Intermediate 52), potassium carbonate (149 mg, 1.081 mmol) and 2-(4-bromo-1H-pyrazol-1-yl)-N-methyl-N-(phenylmethyl)ethanamine (317 mg, 1.078 mmol,... | CC(=O)N1c2ccc(-c3cnn(CCN(C)Cc4ccccc4)c3)cc2[C@H](NC(=O)OC(C)C)C[C@@H]1C | null | null | null |
262,099 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | [C:1]12([CH2:11][CH2:12][N:13]3[C:17]([CH2:18][OH:19])=[CH:16][N:15]=[C:14]3[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[C:1]12([CH2:11][CH2:12][N:13]3[C:17]([CH:18]=[O:19])=[CH:16][N:15]=[C:14]3[CH2:20][CH2:21][CH2:22][CH3:23]... | CCCCc1ncc(CO)n1CCC12CC3CC(CC(C3)C1)C2 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | The above prepared compound (5.4 g) was stirred at room temperature with potassium hydroxide (5.2 g) in ethanol (200 ml) for one hour. The mixture was concentrated, poured into water, stirred and filtered to give 1-[2-(1-adamantyl)ethyl]-2-n-butyl-5-hydroxymethyl-imidazole. The hydroxymethyl group was oxidized by reflu... | CCCCc1ncc(C=O)n1CCC12CC3CC(CC(C3)C1)C2 | null | null | null |
225,901 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | [C:1]([O:4][C:5]1[CH2:9][N:8]([C:10]([CH3:18])([CH3:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:19])[C:6]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:3])[CH3:2]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]([O:4][CH:5]1[CH2:9][N:8]([C:10]([CH3:18])([CH3:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12... | CC(=O)OC1=C(c2ccccc2)C(=O)N(C(C)(C)c2ccccc2)C1 | null | null | [Pd] | O=S(=O)([O-])[O-] | [Ba+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 6.4 g (20 mmol) of 4-acetoxy-1-(α,α-dimethylbenzyl)-2-oxo-3-phenyl-3-pyrroline prepared by the method of reference Example 14, was dissolved in 100 ml of methanol and subjected to hydrogenation at normal temperature under atmospheric pressure by an addition of 0.4 g of Pd-BaSO4. After completion of the reaction, the ca... | CC(=O)OC1CN(C(C)(C)c2ccccc2)C(=O)C1c1ccccc1 | null | 14.8 | null |
1,309,465 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25]([O:32][CH3:33])[CH:24]=3)[CH2:18]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(O)(=O)C.CCOC(C)=O.[BrH:44]>>[BrH:44].[CH3:33][O:32][C:25]1[CH:24]=[C:23]([N:19]2[CH2:20][CH2:21][CH2:22][CH:17]([N:... | COc1cc(N2CCCC(N3CCN(C(=O)OCc4ccccc4)CC3)C2)ccc1[N+](=O)[O-] | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of 4-[1-(3-methoxy-4-nitro-phenyl)-piperidin-3-yl]-piperazine-1-carboxylic acid benzyl ester (300 mg, 0.66 mmol) in 4 M of hydrogen bromide in acetic acid (6 mL, 20 mmol) was heated at 40-45° C. for 45 min, then allowed to cool to room temperature while being stirred overnight. The orange homogenous solution... | COc1cc(N2CCCC(N3CCNCC3)C2)ccc1[N+](=O)[O-] | null | null | null |
1,003,665 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | CS(O[CH2:6][CH2:7][C:8]1[C:9]([C:29]([F:32])([F:31])[F:30])=[N:10][N:11]([CH2:13][C:14]([NH:16][C:17]2[S:21][C:20]3[CH2:22][CH2:23][CH2:24][CH2:25][C:19]=3[C:18]=2[C:26](=[O:28])[NH2:27])=[O:15])[CH:12]=1)(=O)=O.[CH3:33][NH2:34].C(O)=O>CN(C=O)C>[CH3:33][NH:34][CH2:6][CH2:7][C:8]1[C:9]([C:29]([F:30])([F:32])[F:31])=[N:1... | CS(=O)(=O)OCCc1cn(CC(=O)Nc2sc3c(c2C(N)=O)CCCC3)nc1C(F)(F)F | CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | CN(C)C=O | null | null | null | null | null | null | null | null | null | 120 | null | The 2-(1-(2-(3-carbamoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-2-oxoethyl)-3-(trifluoromethyl)1H-pyrazol-4-yl)ethyl methanesulfonate (30 mg, 0.061 mmol) was dissolved in DMF (1 mL) and methylamine (2 M in THF, 1 mL, 2 mmol) added. The reaction mixture was heated at 120° C. for 5 min in the microwave. The THF wa... | CNCCc1cn(CC(=O)Nc2sc3c(c2C(N)=O)CCCC3)nc1C(F)(F)F | null | 13.1 | null |
627,176 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | S(Cl)([Cl:3])=O.[Cl:5][C:6]([Cl:18])=[C:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:8](O)=[O:9].N1C=CC=CC=1>C(OCC)C>[Cl:5][C:6]([Cl:18])=[C:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:8]([Cl:3])=[O:9] | O=C(O)C(=C(Cl)Cl)c1ccc(Cl)cc1 | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | c1ccncc1 | null | null | null | null | null | null | null | null | null | 22.5 | 6 | 35.5 g (0.298 mol) of thionyl chloride were added dropwise at 0° C. to the solution of 50 g (0.199 mol) of the acid of Example 4 in 200 ml of diethyl ether and 23.6 g (0.298 mol) of pyridine. The solution was stirred for 6 hours at 20 to 25° C. and then filtered. After the solvent had been distilled off, 42.1 g of the ... | O=C(Cl)C(=C(Cl)Cl)c1ccc(Cl)cc1 | null | 78.4 | null |
1,010,446 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=1 | OCc1ccc(Cc2cc(Br)ccc2Cl)cc1 | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of (4-(5-bromo-2-chlorobenzyl)phenyl)methanol (intermediate AK) (1 g) in CH2Cl2 (10 mL), the solution of Dess-Martin periodinane (DMP) (1.22 g) in CH2Cl2 (10 mL) was added dropwise at 0° C. The mixture was warmed to room temperature, and the reaction was monitored by TLC. After 1 h, CH2Cl2 was added to di... | O=Cc1ccc(Cc2cc(Br)ccc2Cl)cc1 | null | null | null |
123,517 | ord_dataset-a9b95e50436441ff8f3f12dd60d1e1b2 | null | 1984-01-01T00:10:00 | true | [CH2:1]=[C:2]([CH2:6][C:7]([NH2:9])=[O:8])[C:3](O)=[O:4].C([N:12](CC)CC)C.ClC(OCC)=O>C(Cl)(Cl)Cl>[C:3]([NH2:12])(=[O:4])[C:2]([CH2:6][C:7]([NH2:9])=[O:8])=[CH2:1] | CCN(CC)CC | C=C(CC(N)=O)C(=O)O | null | CCOC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 5 | 2 | 38.7 grams (0.3 mole) of 2-methylenesuccinamic acid, prepared as described in Example 1, were dissolved in 150 ml of chloroform in a 500 ml. 3-necked round bottom flask equipped with a magnetic stirrer, condenser, drying tube, thermometer, and dropping funnel. The solution was cooled to about 5° C. and a mixture of 41.... | C=C(CC(N)=O)C(N)=O | null | null | null |
570,308 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | C([O:3][C:4](=[O:42])[CH2:5][CH:6]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:41])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])=[O:30])=[C:24]([O:39][CH3:40])[CH:23]=2)=[CH:15][CH:14]=1)[CH2:7][C:8]([O:10]CC)=[O:9])C.[OH-].[Na+].Cl>CO>[CH3:40][O:39]... | CCOC(=O)CC(CC(=O)OCC)c1ccc(NC(=O)Cc2ccc(NC(=O)Nc3ccccc3C)c(OC)c2)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 40 | 1 | A mixture of 3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetylamino}phenyl)-pentanedioic acid di-ethyl ester [8.40 g, Reference Example 12(x)] and methanol (400 ml) was heated to 40° C. and then treated with 10% aqueous sodium hydroxide solution (110 ml). After stirring at 40° C. for 1 hour, the reaction mixture... | COc1cc(CC(=O)Nc2ccc(C(CC(=O)O)CC(=O)O)cc2)ccc1NC(=O)Nc1ccccc1C | null | 62 | null |
1,054,174 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | C(O)C.[N+:4]([C:7]1[C:8](=[O:25])[N:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:12]=1)([O-])=O>[H][H].[C].[Pd]>[NH2:4][C:7]1[C:8](=[O:25])[N:9]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]... | O=c1c([N+](=O)[O-])cc(-c2ccccn2)cn1-c1ccccc1 | [H][H] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 100 mg of 10% palladium-carbon was added to 20 ml of an ethanol solution containing 546 mg of 3-nitro-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one, followed by stirring overnight in hydrogen atmosphere. The reaction mixture was filtered through silica gel and concentrated, to give 411 mg of the title compound. | Nc1cc(-c2ccccn2)cn(-c2ccccc2)c1=O | null | 83.8 | null |
1,748,023 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | CS([O:5][CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[Br:19][C:20]1[CH:25]=[CH:24][C:23](O)=[C:22]([O:27][CH3:28])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([O:5][CH2:6][C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([... | CC(C)(C)OC(=O)N1CCC[C@H]1COS(C)(=O)=O | COc1cc(Br)ccc1O | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 100 | 22 | To a solution of (S)-tert-butyl 2-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate (279 mg, 1.00 mmol) and 4-bromo-2-methoxyphenol (325 mg, 1.57 mmol) in N,N-dimethylformamide (5.55 mL) was added cesium carbonate (651 mg, 2.00 mmol). The mixture was heated to 100° C. After 22 h, the mixture was allowed to cool to... | COc1cc(Br)ccc1OC[C@@H]1CCCN1C(=O)OC(C)(C)C | null | null | null |
1,305,158 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18](Cl)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([N:30]1[CH2:34][CH2:33][C@@H:32]([NH2:35])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[CH2:23]([N:30]1[CH2:34][CH2:... | N[C@@H]1CCN(Cc2ccccc2)C1 | O=[N+]([O-])c1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (2 g, 5.9 mmol), (R)-1-Benzyl-pyrrolidin-3-ylamine (2.4 g, 15.3 mmol), and diisopropylethylamine (6 mL, 35.4 mmol) in propan-2-ol (50 mL) was heated to reflux for 4 hours. Volatile components were removed under vacuum and the residue was purified... | O=[N+]([O-])c1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1N[C@@H]1CCN(Cc2ccccc2)C1 | null | 88 | null |
1,033,191 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:18])[C:8](=O)[CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O)[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[C:9]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[NH:3][N:2]=1)=[O:18])[CH3:5] | NN | CCOC(=O)C(=O)C1CCCCCC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | Hydrazine hydrate (0.142 mL, 2.94 mmol) was added to a stirring room temperature solution of 13 (0.6229 g, 2.94 mmol) in EtOH (2.9 mL, 1 M) under N2. The reaction was then heated to reflux until judged complete by TLC (4.5 h): The reaction was concentrated and purified by silica gel chromatography (Combiflash column, 7... | CCOC(=O)c1n[nH]c2c1CCCCC2 | null | 72.3 | null |
408,147 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | [F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].[CH3:8][NH:9][CH:10]([OH:12])[CH3:11]>CC1C=CC(C)=CC=1>[CH3:8][N:9]([CH:10]([OH:12])[CH3:11])[C:3](=[O:4])[C:2]([F:7])([F:6])[F:1] | CNC(C)O | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccc(C)cc1 | null | null | null | null | null | null | null | null | null | null | null | 8 | Trifluoroacetic acid (10 ml; 129 mmol) was added to a stirred solution of N-methylaminoethanol (9.72 g; 129 mmol) in p-xylene (10 ml) at 0° C. The mixture was heated under reflux for 12 hours, then allowed to cool and stand at room temperature overnight. All the volatiles were removed and the product distilled under hi... | CC(O)N(C)C(=O)C(F)(F)F | null | null | null |
695,883 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[NH:20][N:21]=[C:22]([CH3:24])[CH:23]=3)[CH:15]=[C:14]([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[N:13]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:39][N:40]([CH3:45])[CH2:41][CH2:42][CH2:43]Cl>CN(C=O)C>[... | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(O)cc3)n2)cc1 | CN(C)CCCCl | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 80 | 4 | To a solution of the above-prepared [2-(4-acetamido-phenyl-sulfanyl)-6-(4-hydroxyphenyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (70 mg, 1.62.10−4 mol) in DMF (3 mL) is added potassium carbonate (134 mg, 9.71.10−4 mol). The reaction mixture is heated to 80° C. before 1-dimethylamino-3-chloropropane hydrochlori... | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(OCCCN(C)C)cc3)n2)cc1 | null | null | null |
333,679 | ord_dataset-ba1248d90e3e465693710bbc45866f37 | null | 1996-01-01T00:07:00 | true | [O:1]=[C:2]1[C:5](=O)[C:4]([NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[C:3]1[O:16]CC.[CH3:19][C@@H:20]([NH2:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>C(O)C>[O:1]=[C:2]1[C:3](=[O:16])[C:4]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)=[C:5]1[NH:25][C@H:20]([CH3:19])[C:21]([CH3:24]... | C[C@@H](N)C(C)(C)C | CCOc1c(Nc2ccc(C#N)cc2)c(=O)c1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 4-(3,4-Dioxo-2-ethoxy-cyclobut-1-enylamino)-benzonitrile (1 g, 4.1 mmol) and a solution of (R)-1,2,2-trimethylpropylamine (8.2 mmol) in ethanol (50 mL) were stirred at room temperature for 24 hours. The resulting yellow slurry was filtered and rinsed with ethyl acetate to yield 0.92 g (75%) of (+)-(R)-4-[3,4-dioxo-2-(1... | C[C@@H](Nc1c(Nc2ccc(C#N)cc2)c(=O)c1=O)C(C)(C)C | null | 75.5 | null |
5,269 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[NH:15][C:16](=[O:22])[C:17](=[CH:20][CH:21]=3)[C:18]#[N:19])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH-].[K+].I[CH3:26]>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]([CH3:26])[C:16](=[O:22])[C:17](=[CH:20][CH:21]=3)[C:18]#[... | CN1CCN(c2ccc(-c3ccc(C#N)c(=O)[nH]3)cc2)CC1 | CI | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 9.1 g. of 6-[p-(4-methyl-1-piperazinyl)phenyl]-1,2-dihydro-2-oxonicotinonitrile, 2.0 g. of potassium hydroxide, 5.0 ml. of iodomethane and 250 ml. of absolute ethanol is stirred and heated at reflux for 5 hours, then evaporated at reduced pressure. The residue is washed thoroughly with warm water, then dri... | CN1CCN(c2ccc(-c3ccc(C#N)c(=O)n3C)cc2)CC1 | null | null | null |
650,622 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | Br[C:2]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:3]=1[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH2:19](C([Sn])=C(CCCC)CCCC)[CH2:20]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=... | COc1ccc(Br)c(CO[Si](C)(C)C(C)(C)C)c1 | CCCCC([Sn])=C(CCCC)CCCC | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | Under a nitrogen atmosphere, 33.63 9 (0.10 mol) of (2-bromo-5-methoxy-benzyloxy)-tert-butyl-dimethyl-silane (14), 32.18 9 (0.10 mol) of tributylvinyl tin and 4.7 g (0.004 mol) of tetrakis(triphenylphosphine)palladium(0) were combined in 250 mL of toluene, and the solution was heated to reflux for 6 hours. The reaction ... | C=Cc1ccc(OC)cc1CO[Si](C)(C)C(C)(C)C | null | null | null |
663,713 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[Br:12][C:13]1[C:22]2[O:21][CH2:20][CH2:19][NH:18][C:17]=2[CH:16]=[C:15]([Cl:23])[CH:14]=1.[OH-].[Na+]>C(OCC)(=O)C>[CH2:5]([O:4][C:2]([N:18]1[C:17]2[CH:16]=[C:15]([Cl:23])[CH:14]=[C:13]([Br:12])[C:22]=2[O:21][CH2:20][CH2:19]1)=[O:3])[C:6]1[CH:11]=[CH... | Clc1cc(Br)c2c(c1)NCCO2 | O=C(Cl)OCc1ccccc1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 3 | Benzyl chloroformate (1.877 g, 0.011 mol) was added dropwise to a solution of 8-bromo-6-chloro-3,4-dihydro-2H-benzo[1,4]oxazine (2.85 g, 0.01 mol) in a 1:1 mixture of ethyl acetate (30 mL) and 10% aqueous sodium hydroxide (30 mL). After 3 hours at ambient temperature, the layers were separated and the organic phase was... | O=C(OCc1ccccc1)N1CCOc2c(Br)cc(Cl)cc21 | null | 90.7 | null |
1,165,254 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>>[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | ClCCCCBr | C1CCNCC1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | In a 2 L three-necked round bottomed flask was added piperidine (85.15 g, 1.0 mol) acetone (1000 mL), and anhydrous potassium carbonate (276.42 g, 2.0 mol, 2.0 equiv.). The flask was equipped with a mechanical stirrer and a condenser. 4-chloro-1-bromo-butane (188.6 g, 1.1 mol, 1.1 equiv.) was added dropwise under conti... | ClCCCCN1CCCCC1 | null | 56 | null |
258,120 | ord_dataset-2369b9b9f44641b1930518c59ae89a95 | null | 1992-01-01T00:11:00 | true | [OH:1][CH:2]([CH2:13][OH:14])[CH2:3][CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>O1CCCC1.CCOCC>[Si:20]([O:14][CH2:13][CH:2]([OH:1])[CH2:3][CH2:4][P:5](=[O:12])([O:6][CH2:7][CH3:8])[O:9][CH2:10][CH3:11])([C:23]([CH3:26])([CH3:... | CCOP(=O)(CCC(O)CO)OCC | CC(C)(C)[Si](C)(C)Cl | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 0.03 | To a solution of diethyl 3,4-dihydroxybutylphosphonate (8.5 g, 0.038 mol) in dry tetrahydrofuran (200 ml) was added imidazole (5.25 g, 0.077 mol). After stirring at ambient temperature for 2 minutes, t-butyldimethysilyl-chloride (5.8 g, 0.038 mol) was added. After 18 hours, the solution was filtered and the filtrate ev... | CCOP(=O)(CCC(O)CO[Si](C)(C)C(C)(C)C)OCC | null | null | null |
1,548,745 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:6][C@@H:5]1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]2([CH3:19])[CH2:18][CH2:17]2)=[O:14])[CH2:9][CH2:8]1.[F:20][C:21]1[CH:26]=[C:25](O)[CH:24]=[CH:23][C:22]=1[CH2:28][C:29]([O:31][CH3:32])=[O:30].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>ClCCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:... | CC1(OC(=O)N2CCC([C@H]3C[C@H]3CCO)CC2)CC1 | COC(=O)Cc1ccc(O)cc1F | null | CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 1-methylcyclopropyl 4-[(1R,2S)-2-(2-hydroxyethyl)cyclopropyl]piperidine-1-carboxylate (Intermediate 9, 0.484 g, 1.81 mmol) in 5 ml anhydrous dichloromethane at RT was added a solution of methyl (2-fluoro-4-hydroxyphenyl)acetate (0.400 g, 2.17 mmol) in 10 ml anhydrous dichloromethane, triphenylphosphine... | COC(=O)Cc1ccc(OCC[C@@H]2C[C@@H]2C2CCN(C(=O)OC3(C)CC3)CC2)cc1F | null | null | null |
214,579 | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | null | 1990-01-01T00:09:00 | true | Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.[Na].[H-].[Na+].N1C=CN=C1>CN(C=O)C>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)[CH:16]=[CH:15][N:14]=[CH:13]1 | COC(=O)c1ccc(Cl)nc1 | c1c[nH]cn1 | null | [H-] | [Na+] | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 120 | null | A solution of the methyl ester obtained in Step 1. above (16.29 g) in DMF is added dropwise to a DMF suspension of sodium imidazole [prepared from NaH (4.19 g) and imidazole 6.49 g)] at RT. The reaction mixture is heated to 120° C. for nineteen hours. The cooled reaction mixture is partitioned between water and chlorof... | COC(=O)c1ccc(-n2ccnc2)nc1 | null | null | null |
1,109,429 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [NH2:1][C:2]1[S:3][C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[C:5]([C:7]([N:9]2[CH2:14][C@H:13]3[C@H:11]([CH2:12]3)[C@H:10]2[CH2:15][NH2:16])=[O:8])[N:6]=1.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([C:33](O)=[O:34])=[CH:25]1>>[NH2:1][C:2]1[S:3][C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[C... | NC[C@@H]1[C@H]2C[C@H]2CN1C(=O)c1nc(N)sc1-c1cccc(F)c1 | O=C(O)c1c[nH]c2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | prepared by reaction of [2-Amino-5-(3-fluoro-phenyl)-thiazol-4-yl]-((1S,2S,5R)-2-aminomethyl-3-aza-bicyclo[3.1.0]hex-3-yl)-methanone with 1H-Indole-3-carboxylic acid. LC-MS (basic): tR=0.76 min; [M+H]+=476.3. | Nc1nc(C(=O)N2C[C@@H]3C[C@@H]3[C@H]2CNC(=O)c2c[nH]c3ccccc23)c(-c2cccc(F)c2)s1 | null | null | null |
450,607 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | CO[C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]3([CH3:19])[O:18]CCO3)[CH:12]=2)[N:7]([CH2:20][CH3:21])[C:6]1=[O:22])=[O:4].[NH2:23][C:24]1[CH:25]=[C:26]([CH:37]=[CH:38][CH:39]=1)[C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)=[O:28]>>[F:36][C:33]1[CH:34]=[CH:35][C:30]([NH:29][C:27]([C:26]2... | Nc1cccc(C(=O)Nc2ccc(F)cc2)c1 | CCN1C(=O)C(C(=O)OC)c2cc(C3(C)OCCO3)ccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared as in Example 1 from 1-ethyl-5-(2-methyl-[1,3]dioxolan-2-yl)-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid methyl ester and 3-amino-N-(4-fluoro-phenyl)-benzamide. Recrystallized from ethyl acetate-hexanes-benzene. Calculated for C26H22FN3O4 : C 67.97; H 4.83; N 9.15; found C 68.34; H 5.31; N 8.80. | CCN1C(=O)C(C(=O)Nc2cccc(C(=O)Nc3ccc(F)cc3)c2)c2cc(C(C)=O)ccc21 | null | null | null |
694,263 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][C:9](=[O:11])[CH3:10])=S)=[CH:4][CH:3]=1.Cl.Cl.[NH2:16][CH:17]([CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:18]([NH:20][C:21]1([C:28]#[N:29])[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1)=[O:19]>>[C:9]([N:8]=[C:6]([NH:16][CH:17]([CH2:30][CH:31]1[CH2:32][C... | CC(=O)NC(=S)c1ccc(F)cc1 | CN1CCC(C#N)(NC(=O)C(N)CC2CCCCC2)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared starting from N-(4-fluoro-thiobenzoyl) acetamide and 2-amino-N-(4-cyano-1-methyl-piperidin-4-yl)-3-cyclohexyl-propionamide bis hydrochloride salt according to the procedure from Example 72, step b. MS, m/z 456=M+1. | CC(=O)N=C(NC(CC1CCCCC1)C(=O)NC1(C#N)CCN(C)CC1)c1ccc(F)cc1 | null | null | null |
1,357,282 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.[NH:21]1[CH2:26][CH2:25][C:24]2([C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=[CH:27]2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:21]3[CH2:26][CH2:25][C:24]4... | C1=CC2(CCNCC2)c2ccccc21 | Cc1nsc(-c2ccc(Cl)nn2)n1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | The object product (22 mg, 25%) was obtained in the same manner as in Example 1 and using 3-chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazine (51 mg), spiro[indene-1,4′-piperidine] trifluoroacetate (105 mg) and potassium carbonate (70 mg). | Cc1nsc(-c2ccc(N3CCC4(C=Cc5ccccc54)CC3)nn2)n1 | null | null | null |
222,178 | ord_dataset-42629b4cf1094978a5e5f29f22639ee7 | null | 1991-01-01T00:01:00 | true | [OH:1][CH2:2][C:3]1[CH2:8][C:7](=[O:9])[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][N:4]=1.C([O:23][CH2:24][CH3:25])(=O)C>CO.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[N:4]([O:23][CH:24]([C:25]2[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C... | CCOC(C)=O | COc1ccc(COC2=CN=C(CO)CC2=O)cc1 | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | In 300 ml of anhydrous methanol is suspended 6 g of 2-hydroxymethyl-5-p-methoxybenzyloxy-4-pyridone, and 15 g of active manganese dioxide is added thereto. The reaction is performed under heating at a refluxing temperature for 30 minutes. At the end of the reaction, the manganese dioxide is removed by filtration, and t... | COc1ccc(COc2cn(OC(c3ccccc3)c3ccccc3)c(C=O)cc2=O)cc1 | null | null | null |
389,228 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | [NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:7][N:8]=[C:9]=[O:10]>ClCCl>[CH3:7][NH:8][C:9]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:10] | C1CNCCN1 | CN=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | To the solution of piperazine (3 g) in dichloromethane (30 ml) was added methyl isocyanate (2.16 ml) in an ice water bath with stirring. After 10 minutes the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was evaporated in vacuo. The residue was diluted with acetonitrile (15 ml) and crystal... | CNC(=O)N1CCNCC1 | null | null | null |
721,868 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8]/[N:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12].[Br:15]N1C(=O)CCC1=O>O1CCCC1>[Br:15]/[C:10](=[N:9]\[NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])/[C:11]([O:13][CH3:14])=[O:12] | O=C1CCC(=O)N1Br | COC(=O)/C=N/Nc1ccccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of the title compound of Step A (16.5 g, 77 mmol) in tetrahydrofuran (150 mL) was added N-bromosuccinimide (13.7 g, 77 mmol) and the mixture was stirred at ambient temperature for 2 hours. The mixture was concentrated and extracted with hexane and the hexane solution was concentrated to give the title com... | COC(=O)/C(Br)=N/Nc1ccccc1Cl | null | 71.3 | null |
419,783 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | [C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](=[O:22])NCOC)=[CH:14][CH:15]=2)[C:10]([CH2:23][CH2:24][N:25]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:9]1[C:43]1[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[CH:... | [Li]C | COCNC(=O)c1ccc2c(c1)c(CCN(CCCCc1ccncc1)C(=O)OC(C)(C)C)c(-c1cc(C)cc(C)c1)n2C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | 0.75 | To a solution of 3-{2-[tert-butoxycarbonyl-(4-pyridin-4-yl-butyl)amino]ethyl}-2-(3,5 -dimethylphenyl)-5-(methoxymethylcarbamoyl) indole-1-carboxylic acid tert-butyl ester (0.069 g in 3 mL dry tetrahydrofuran) at -10° C. was added 0.20 mL of a 1.5M solution of methyllithium in ether and the mixture stirred at low temper... | CC(=O)c1ccc2c(c1)c(CCN(CCCCc1ccncc1)C(=O)OC(C)(C)C)c(-c1cc(C)cc(C)c1)n2C(=O)OC(C)(C)C | null | null | null |
1,576,757 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[CH:4][C:3]=1[OH:15].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26]>CC(C)=O>[CH3:14][C:12]1[N:13]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([O:15][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH:4]=2)[S:10][C... | Cc1csc(Nc2ccc(C)c(O)c2)n1 | CC(C)=CCBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure general for O-alkylation, Method A, a mixture of 2-methyl-5-(4-methylthiazol-2-ylamino)phenol (79 mg, 0.36 mmol) and K2CO3 (54 mg, 0.39 mmol) in acetone (3.6 mL) was treated with 4-bromo-2-methyl-2-butene (0.05 mL, 0.43 mmol). The reaction mixture was heated at reflux for 4 h. The title compound... | CC(C)=CCOc1cc(Nc2nc(C)cs2)ccc1C | null | 56 | null |
200,840 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[S:26] | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | O=C(Nc1ccccc1F)c1ccccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | N-(2-fluorophenyl)-2-pyridinecarboxamide (11.81 g, 55 mmol) was reacted with Lawesson's reagent (26.04 g, 64 mmol) in toluene (160 mL) at reflux temperature for 5 hours. The solution was preadsorbed onto silica gel and flash chromatographed (eluted with 2.5% ethyl acetate in petroleum ether) to give N-(2-fluorophenyl)-... | Fc1ccccc1NC(=S)c1ccccn1 | null | 56.8 | null |
1,366,812 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [C:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:19]([CH3:21])([CH3:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:22]([O:24]C)=[O:23])[CH:16]=3)[NH:11]2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2].[OH-].[Na+]>CO>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:19]([CH3:21])([CH3:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:22]([OH:24])=[... | COC(=O)c1ccc2c(c1)CC(C)(C)C(c1cccc(C(N)=O)c1)N2 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of methyl 2-(3-carbamoylphenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxy late (84 mg, 0.25 mmol) in methanol (4.5 mL) and 1 M sodium hydroxide aqueous solution (3.2 mL, 3.2 mmol, 13.0 eq.) was heated to reflux for 30 min, LC-MS showed the reaction was complete and only the desired product formed. Th... | CC1(C)Cc2cc(C(=O)O)ccc2NC1c1cccc(C(N)=O)c1 | null | null | null |
1,404,933 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:16]3[N:17]([C:21]([C:24]4[CH:29]=[CH:28][N:27]=[C:26](S(C)=O)[N:25]=4)=[CH:22][N:23]=3)[CH:18]=[CH:19][N:20]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37][NH2:38]>>[C:1]([O:5][C:6](... | NCc1ccccc1Cl | CS(=O)c1nccc(-c2cnc3c(NC4CCC(NC(=O)OC(C)(C)C)CC4)nccn23)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 140 | 2 | The mixture of {4-[3-(2-methanesulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (from Example 48 supra) (100 mg, 0.21 mmol) and 2-chlorobenzylamine (120 mg, 0.84 mmol) was heated at 140° C. with stirring for 2 hours. The oil was purified by chromatography (silica gel,... | CC(C)(C)OC(=O)NC1CCC(Nc2nccn3c(-c4ccnc(NCc5ccccc5Cl)n4)cnc23)CC1 | null | null | null |
901,137 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [C:1]1([S:7]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12](O)=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:21])=O.CN(C)C=O>ClCCl.C(=O)(O)[O-].[Na+]>[C:1]1([S:7]([N:10]2[CH2:17][CH2:16][CH2:15][CH:11]2[C:12]([Cl:21])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | O=C(O)[C@@H]1CCCN1S(=O)(=O)c1ccccc1 | O=C(Cl)C(=O)Cl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of the N-phenylsulfonyl proline (1.5 g, 5.8 mmol) in anhydrous dichloromethane (20 mL), were added oxalyl chloride (2.0 M in dichloromethane, 5.9 mL, 11.8 mmol) and a catalytic amount of dimethylformamide. The solution was stirred for 1 hour at room temperature. The reaction mixture was then condensed and... | O=C(Cl)C1CCCN1S(=O)(=O)c1ccccc1 | null | 13.9 | null |
1,657,034 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16][CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:5]([NH:13][C@H:14]2[CH2:15][CH2:16][C@H:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][CH2:19]2)=[C:6]... | CCOC(=O)C[C@H]1CC[C@H](Nc2c([N+](=O)[O-])cnc3ccsc23)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Ethyl {trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetate (160 mg, 0.44 mmol) and 10% Pd/C (20 mg) in methanol (4 mL) was subjected to balloon pressure of H2 at room temperature for 2 h. The mixture was filtered. The filtrate was concentrated and purified on silica gel column (eluting with 0-10% MeOH i... | CCOC(=O)C[C@H]1CC[C@H](Nc2c(N)cnc3ccsc23)CC1 | null | null | null |
1,241,958 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | C(Cl)Cl.[CH2:4]([C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:11]... | CCCCc1nc(Cl)c(CO)n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CS(=O)(=O)Cl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | -78 | 0.25 | To a DCM (200 mL) solution of intermediate (11b) (13.6 g, 20.4 mmol), cooled to −78° C., was added methane sulfonyl chloride (6.3 mL, 81.6 mmol). The mixture was stirred at −78° C. for 15 minutes. A saturated NaHCO3 solution (100 mL) and EtOAc (500 mL) were added to the cooled mixture, which was then allowed to reach r... | CCCCc1nc(Cl)c(COS(C)(=O)=O)n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | 98.9 | null |
614,071 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]3[CH2:14][CH2:13][CH2:12]3)=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:23]2[CH:24]=[C:25]([C:29]3[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:26]=[CH:27][CH:28]=2)O1>>[CH:11]1([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([C:27]4[CH:26]=[C:25]([C:29]5[C:30]([C:35]#[N:36])=[CH:31... | CC1(C)OB(c2cccc(-c3ccccc3C#N)c2)OC1(C)C | Brc1cnc2nc(C3CCC3)ccn12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-Bromo-7-cyclobutylimidazo[1,2-a]pyrimidine was coupled with 3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 3′-(7-cyclobutylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile as a white powder: δH (400 MHz, CDCl3) 1.90-2.55 (6H, m), 3.77 (1H, quintet, J 8),... | N#Cc1ccccc1-c1cccc(-c2cnc3nc(C4CCC4)ccn23)c1 | null | null | null |
1,445,298 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH:12]([N:15]=[C:16]=[O:17])([CH3:14])[CH3:13]>C(OCC)(=O)C>[CH:12]([NH:15][C:16]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2)=[O:17])([CH3:14])[CH3:13] | CC(C)N=C=O | Nc1ccc2c(c1)CC(=O)N2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To 5-aminoindolin-2-one (50 mg, 0.34 mmol) in ethyl acetate (1 mL) was added isopropylisocyanate (0.04 mL, 0.4 mmol). The solution was stirred at rt for 16 h and the product was precipitated with ether, filtered and dried to give 46 mg, 58% of a yellow solid. 1H NMR (400 MHz, CD3OD) δ 7.31 (s, 1H), 7.13 (d, J=8.3 Hz, 1... | CC(C)NC(=O)Nc1ccc2c(c1)CC(=O)N2 | null | 58 | null |
1,627,786 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:35]=[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C@@H:25]([C:32]#[C:33][CH3:34])[CH2:26][C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=3)=[CH:16][N:11]2[N:10]=1.[OH-].[Na+]>CCO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]... | CC#C[C@@H](CC(=O)OCC)c1ccc(OCc2ccc3nc(-c4c(C)cccc4C)nn3c2)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 80 | 0.5 | To a solution of ethyl (3S)-3-[4-[[2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]methoxy]phenyl]hex-4-ynoate (0.22 g, 0.47 mmol) in EtOH (20 mL) is added 5 N NaOH (0.3 mL) and the reaction mixture is stirred at 80° C. in a microwave instrument for 30 minutes. The reaction mixture is evaporated to dryness, d... | CC#C[C@@H](CC(=O)O)c1ccc(OCc2ccc3nc(-c4c(C)cccc4C)nn3c2)cc1 | null | 75 | null |
142,179 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | [Na].[Cl:2][C:3]1[C:4](=[O:12])[O:5][C:6](C)([CH3:10])[O:7][C:8]=1[CH3:9]>C(O)C>[CH2:6]([O:5][C:4](=[O:12])[CH:3]([Cl:2])[C:8]([CH3:9])=[O:7])[CH3:10] | CC1=C(Cl)C(=O)OC(C)(C)O1 | null | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Sodium metal (0.3 g, 12 mmol) was added to 10 ml of ethanol, and then 5-chloro-2,2,6-trimethyl-4H-1,3-dioxin-4-one (1.76 g, 10 mmol) was added. The reaction was stirred one hour at 20° C., during which time the sodium dissolved. The reaction partitioned between ether and saturated ammonium chloride which had been acidi... | CCOC(=O)C(Cl)C(C)=O | null | 69.9 | null |
73,951 | ord_dataset-b9d8ddf9c2884d40859b6b5f24815a7d | null | 1980-01-01T00:12:00 | true | [CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([OH:15])[CH:8]=[C:9]([CH:13]=[O:14])[CH:10]=2)[C:5](=[O:16])[CH2:4]1)[CH3:2].[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([O:15][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:8]=[C:9]([CH:13]=[O:1... | BrCc1ccccc1 | CCC1CC(=O)c2c(O)cc(C=O)cc2C1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product of Example 30 is treated with sodium hydride and benzyl bromide according to the procedure described in Example 15. | CCC1CC(=O)c2c(cc(C=O)cc2OCc2ccccc2)C1 | null | null | null |
971,039 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([NH2:11])=[C:6]([NH2:12])[CH:5]=1.CO[C:16](=[NH:21])[C:17]([Cl:20])([Cl:19])[Cl:18]>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([CH3:10])[C:7]2[NH:11][C:16]([C:17]([Cl:20])([Cl:19])[Cl:18])=[N:12][C:6]=2[CH:5]=1)=[O:13].[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([CH3:10])... | COC(=O)c1cc(C)c(N)c(N)c1 | COC(=N)C(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 7-Methyl-2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester 7-Methyl-2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester was prepared by a procedure according to example 5 (i) starting from 404.0 mg (2.20 mmol) 3,4-Diamino-5-methyl-benzoic acid methyl ester and 0.39 mL (3.08 mmol) 2,2,2-t... | COC(=O)c1cc(C)c2[nH]c(C(Cl)(Cl)Cl)nc2c1 | null | null | null |
396,937 | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | null | 1998-01-01T00:04:00 | true | [O:1]=[C:2]1[CH:11]=[CH:10][C:9](=[O:12])[C:8]2[CH2:7][O:6][CH:5]([CH2:13][CH3:14])[CH2:4][C:3]1=2.C(O[CH:19]=[CH:20][CH:21]=[CH2:22])(=O)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:13]([CH:5]1[O:6][CH2:7][C:8]2[C:9](=[O:12])[C:10]3[C:11]([C:2](=[O:1])[C:3]=2[CH2:4]1)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:14] | CCC1CC2=C(CO1)C(=O)C=CC2=O | C=CC=COC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | Following the procedure described in step 4, example 26, the starting quinone from step 3 herein (250 mg; 1.30 mmol) and 1-acetoxy-1,3-butadiene (876 μl; 7.8 mmol) were reacted in toluene (10 ml) to yield after chromatography using 2% ethyl acetate in toluene the title compound (62 mg; 20%) along with mixed fractions c... | CCC1CC2=C(CO1)C(=O)c1ccccc1C2=O | null | 20 | null |
1,445,496 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([NH:21]C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:5]=[N:4][CH:3]=[N:2]1>FC(F)(F)C(O)=O>[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:16][CH2:17][CH:18]([NH2:21])[CH2:19][CH2:20]3)=[CH:13][CH:14]=2)[C... | CC(C)(C)OC(=O)NC1CCN(c2ccc(CCCn3cncn3)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 25 | 1 | The N-(4-(3-(1,2,4-triazol-1-yl)-propyl)-phenyl)-4-tert-butoxycarbonylaminopiperidine (180 mg, 0.47 mmol) obtained in Example 8(5) was dissolved in trifluoroacetic acid (5 ml) at 0° C., followed by stirring at room temperature for 1 hour. The reaction mixture was evaporated under reduced pressure, and the obtained resi... | NC1CCN(c2ccc(CCCn3cncn3)cc2)CC1 | null | null | null |
122,880 | ord_dataset-a9b95e50436441ff8f3f12dd60d1e1b2 | null | 1984-01-01T00:10:00 | true | C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]([NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24](=[N:40][O:41][CH3:42])[C:25]([NH:27][CH:28]2[C:38](=[O:39])[N:30]3[C:31]([C:35]([OH:37])=[O:36])=[CH:32][CH2:33][S:34][C@H:29]23)=[O:26])[N:23]=1)=[O:17].[CH2:43]([O:55][CH2:56][CH:57]([CH2:59][O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66... | CCCCCCCCCCCCOCC(O)COCCCCCCCCCCCC | CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=CCS[C@H]12)c1csc(NC=O)n1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 4.75 | Dicyclohexylcarbodiimide (3.96 g) was added to a stirred solution of 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 6.58 g] and 2-n-dodecyloxy-1-n-dodecyloxymethylethanol (8.23 g) in a mixture of dry pyridine (60 ml) and dry tetrahydrofuran (20 ml) at 3° C., and then sti... | CCCCCCCCCCCCOCC(COCCCCCCCCCCCC)OC(=O)C1C=CS[C@@H]2C(NC(=O)C(=NOC)c3csc(NC=O)n3)C(=O)N12 | null | null | null |
1,103,241 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | Br[C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([C:17]([O:19][CH3:20])=[O:18])[C:3]=1[CH3:21].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=... | COC(=O)c1cn(S(=O)(=O)c2cccc(Cl)c2)c(Br)c1C | OB(O)c1ccccc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | null | null | Methyl 5-bromo-1-[(3-chlorophenyl)sulfonyl]-4-methyl-1H-pyrrole-3-carboxylate (1.0 g), phenylboronic acid (403 mg), sodium carbonate (405 mg) and tetrakis(triphenylphosphine)palladium (295 mg) were suspended in a mixture of 1,2-dimethoxyethane (10 mL) and distilled water (10 mL), and the mixture was reacted in a microw... | COC(=O)c1cn(S(=O)(=O)c2cccc(Cl)c2)c(-c2ccccc2)c1C | null | 72.9 | null |
1,023,620 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=O.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[CH3:10][C:7]1[CH:8]=[CH:9][C:2]2[O:1][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][C:3]=2[CH:6]=1 | CCOC(=O)CBr | Cc1ccc(O)c(C=O)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a stirred suspension of 2-hydroxy-5-methylbenzaldehyde (5 g, 36.7 mmol) and K2CO3 (12.7 g, 91.8 mmol) in DMF (30 mL), ethyl bromoacetate (4.07 ml, 36.7 mmol) was added drop-wise. This mixture was allowed to stir for two hours under nitrogen at room temperature, and was then heated to 80° C. and stirred overnight. Th... | CCOC(=O)c1cc2cc(C)ccc2o1 | null | 30.7 | null |
1,666,991 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:13][C:12]=1[F:21].[OH-].[Na+].Cl>C1COCC1.CO>[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][C:12]=1[F:21] | COC(=O)c1ccc(F)c(-c2c(F)cc(SC)cc2F)n1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 0.83 | Methyl 6-[2,6-difluoro-4-(methylthio)phenyl]-5-fluoropyridine-2-carboxylate (80.0 mg, 0.255 mmol) was dissolved in THF (0.3 mL) and MeOH (0.3 mL), then 1.0 M aq. NaOH (1.28 mL, 1.28 mmol) was added. The reaction mixture was stirred at room temperature for 50 min., then neutralized with HCl (12 M) to pH=7 and concentrat... | CSc1cc(F)c(-c2nc(C(=O)O)ccc2F)c(F)c1 | null | 55 | null |
1,688,748 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [Li]CCCC.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([Si:14]([CH3:17])([CH3:16])[CH3:15])=[C:9]([F:18])[CH:8]=1.[CH:19](N1CCOCC1)=[O:20]>C1COCC1>[Cl:6][C:7]1[C:8]([CH:19]=[O:20])=[C:9]([F:18])[C:10]([Si:14]([CH3:15])([CH3:17])[CH3:16])=[C:11]([F:13])[CH:12]=1 | O=CN1CCOCC1 | C[Si](C)(C)c1c(F)cc(Cl)cc1F | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -70 | null | A solution of 2.5M n-BuLi in hexanes (60 ml, 0.15 mol) was added drop-wise to a solution of (4-chloro-2,6-difluorophenyl)trimethylsilane (assumed 0.13 mol) in THF (180 mL) cooled to −70° C. under Ar. After the addition was complete, the mixture was stirred for 1 h before a solution of N-formylmorpholine (20 mL, 0.2 mol... | C[Si](C)(C)c1c(F)cc(Cl)c(C=O)c1F | null | 108.2 | null |
1,425,358 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([CH3:11])[S:8][C:7]=2[CH:12]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19]>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:18](=[O:19])[C:17]3[CH:16]=[C:15]([O:14][CH3:13])[C:23]([O:24][CH3:25])=[C:22... | COc1cc(C(=O)Cl)cc(OC)c1OC | COc1ccc2cc(C)sc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | 40 | 1 | To a mixture of 6-methoxy-2-methylbenzo[b]thiophene (0.024 g; 0.132 mmol) and 3,4,5-trimethoxybenzoyl chloride (0.052 g; 0.225 mmol) in 1,2-dichloroethane (1 ml) SnCl4 (0.023 ml) was added. The resulting mixture was stirred for 1 h at 40° C., quenched with H2O (1 ml), diluted to 15 ml with diethyl ether, washed with 5%... | COc1ccc2c(C(=O)c3cc(OC)c(OC)c(OC)c3)c(C)sc2c1 | null | 40.7 | null |
1,116,005 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=O)[CH:9]=2)=[CH:6][C:5]([CH2:16][NH:17][C:18](=[O:45])[CH2:19][CH2:20][C:21]([NH:23][CH2:24][C:25]2[C:26]([NH:38][CH:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[C:27]3[CH:35]=[N:34][N:33]([CH2:36][CH3:37])[C:28]3=[N:29][C:30]=2[CH2:31][CH3:32])=[O:22])=[CH... | C[C@H]1CNCCN1C(=O)OC(C)(C)C | CCc1nc2c(cnn2CC)c(NC2CCOCC2)c1CNC(=O)CCC(=O)NCc1ccc(Cl)c(-c2cccc(C=O)c2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 4 | N-[(6-Chloro-3′-formyl-3-biphenylyl)methyl]-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}butanediamide (37.8 mg. 0.06 mmol) was diluted in DMSO (1.5 mL) and dispensed into a 1 dram vial containing 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (0.18 mmol), acetic aci... | CCc1nc2c(cnn2CC)c(NC2CCOCC2)c1CNC(=O)CCC(=O)NCc1ccc(Cl)c(-c2cccc(CN3CCNCC3)c2)c1 | null | 16.4 | null |
1,690,969 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11](COCC[Si](C)(C)C)[N:10]=2)=[N:6][C:7]=1F.[NH:32]1[CH2:36][CH2:35][C@@H:34]([NH:37]C(=O)OC(C)(C)C)[CH2:33]1>>[Br:1][C:2]1[C:7]([N:32]2[CH2:36][CH2:35][C@@H:34]([NH2:37])[CH2:33]2)=[N:6][... | C[Si](C)(C)CCOCn1nc(-c2ccc(Br)c(F)n2)c2cc(-c3cccnc3)ncc21 | CC(C)(C)OC(=O)N[C@@H]1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedures as described in Example 241 and starting with 3-(5-bromo-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine and (R)-tert-butyl pyrrolidin-3-ylcarbamate, 287 was obtained as an off-white solid (12.2 mg, 34%) over two steps. 1H NMR (400 MHz, DMS... | N[C@@H]1CCN(c2nc(-c3n[nH]c4cnc(-c5cccnc5)cc34)ccc2Br)C1 | null | 34 | null |
854,760 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [C:1]([C:4]1[C:5]([C:22](=[O:24])[CH3:23])=[C:6]([CH3:21])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16]CC)=[CH:12][C:11]=2[O:19][CH3:20])[C:8]=1[CH3:9])(=[O:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:22]([C:5]1[C:4]([C:1](=[O:3])[CH3:2])=[C:8]([CH3:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[O:19][CH3:20])[C:6]=1... | CCOc1ccc(-n2c(C)c(C(C)=O)c(C(C)=O)c2C)c(OC)c1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a stirring solution of crude 1-[4-acetyl-1-(4-ethoxy-2-methoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone prepared as above (90 mg, 0.3 mmol) in 5.0 mL of CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 0.9 mL, 0.9 mmol). After 1 h at 0° C., it was warmed to rt and stirred for an additional 2 h before it was que... | COc1cc(O)ccc1-n1c(C)c(C(C)=O)c(C(C)=O)c1C | null | null | null |
581,349 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[N:10]2[CH2:13][C:12](=[C:14]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=3)[S:15]([CH3:18])(=[O:17])=[O:16])[CH2:11]2)=[CH:5][CH:4]=1.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>ClCCl>[Cl:33][C:30]1[CH... | C1CCNCC1 | CS(=O)(=O)C(=C1CN([C@@H](c2ccc(Cl)cc2)c2ccc(CCl)cc2)C1)c1cc(F)cc(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | The operation is carried out as described in Example 87, starting with 0.05 g of 1-{(R*)-[4-(chloromethyl)phenyl](4-chlorophenyl)methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine, form A isomer, 1.0 cm3 of dichloromethane, and 0.017 g of piperidine. The crude product is chromatographed on a silica gel ... | CS(=O)(=O)C(=C1CN([C@@H](c2ccc(Cl)cc2)c2ccc(CN3CCCCC3)cc2)C1)c1cc(F)cc(F)c1 | null | 63.9 | null |
1,306,237 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[N+:19]([O-])=O.[NH4+].[Cl-]>[Fe].CCO>[NH2:19][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:2]=1[F:1])[CH2:6][NH:7][C:8]([C:10]1([C:13]([F:14])([F:15])[F:16])[CH2:11][CH2:12]1)=[O:9] | O=C(NCc1ccc(F)c([N+](=O)[O-])c1)C1(C(F)(F)F)CC1 | null | null | [Fe] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | The sub-title compound was prepared in analogy to the procedure in Example 93, step (c) using N-(4-fluoro-3-nitrobenzyl)-1-(trifluoromethyl)-cyclopropanecarboxamide (3.77 g; 12.3 mmol), Fe (3.45 g; 61.6 mmol), NH4Cl (aq, sat, 30 mL) and EtOH (30 mL). | Nc1cc(CNC(=O)C2(C(F)(F)F)CC2)ccc1F | null | null | null |
1,019,911 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH3:1][C:2]1[C:3]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.[NH2:17][CH2:18][CH2:19][N:20]1[CH2:24][CH2:23][NH:22][C:21]1=[O:25].C1(C)C=CC=CC=1>ClCCl>[CH3:1][C:2]1[C:3]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:4][C:5]([NH:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][NH:22][C:21]2=[O:25... | Cc1cnc(S(C)(=O)=O)nc1-c1cccs1 | NCCN1CCNC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 200 | null | 5-Methyl-2-(methylsulfonyl)-4-(thiophen-2-yl)pyrimidine (0.1 g, 0.39 mmol) and 1-(2-aminoethyl)imidazolidin-2-one (0.06 g, 047 mmol) were added to a microwave tube along with toluene (1 mL). The tube was capped and heated to 200° C. for 10 min in a Personal Chemistry microwave. The mixture was diluted with dichlorometh... | Cc1cnc(NCCN2CCNC2=O)nc1-c1cccs1 | null | null | null |
1,138,825 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [C:1]([C:4]1[N:12]2[C:7]([C:8]([NH2:13])=[N:9][CH:10]=[N:11]2)=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=3[F:34])=[O:22])=[CH:16][CH:15]=2)[CH:5]=1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[Br:56]N1C(C)(C)C(=O)... | CC1(C)C(=O)N(Br)C(=O)N1Br | CC(=O)c1cc(-c2ccc(NC(=O)Nc3cc(C(F)(F)F)ccc3F)cc2)c2c(N)ncnn12 | null | C[Si](C)(C)OS(=O)(=O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 1 | A suspension of Example 100 in THF (5 mL) was cooled to −78° C. and treated with diisopropylethyl amine (0.424 mL, 2.57 mmol) followed by trimethylsilyltriflate (0.421 mL, 2.177 mmol). The reaction was allowed to warm to rt over 30 min, then cooled again to −78° C. and treated with 1,3-dibromo-5,5-dimethylhydantoin (62... | Nc1ncnn2c(C(=O)CBr)cc(-c3ccc(NC(=O)Nc4cc(C(F)(F)F)ccc4F)cc3)c12 | null | 70 | null |
434,811 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [CH2:1]([N:8]([CH2:10][CH2:11][OH:12])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1>>[CH2:1]([N:8]([CH2:10][CH2:11][O:12][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | O=Cc1ccc(F)cc1 | CN(CCO)Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-(N-benzyl-N-methylamino)ethanol (2.5 g) obtained in example 8 and 4-fluorobenzaldehyde (2 ml) by an analogous procedure to that described in preparation 23. | CN(CCOc1ccc(C=O)cc1)Cc1ccccc1 | null | null | null |
151,396 | ord_dataset-772de90433b44abbbacf9b316b845c31 | null | 1986-01-01T00:12:00 | true | [CH3:1][O:2][CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)[CH2:4][NH2:5].[C:13]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:21][CH:20]=1)([O:15][CH3:16])=[O:14].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[C:13]([CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2... | COC(CN)c1cccc(Cl)c1 | COC(=O)COc1ccc(CCOS(=O)(=O)c2ccc(C)cc2)cc1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CS(C)=O | null | null | null | null | null | null | null | null | null | 55 | null | A mixture of 2-methoxy-2-(3-chlorophenyl)ethanamine (1.81 g), 2-(4-carbomethoxymethoxyphenyl)-1-(p-toluenesulphonyloxy)ethane (4.0 g) and triethylamine (4 ml) in dimethyl sulphoxide (50 ml) was heated at 55° C. After 24 h the solution was poured into saturated sodium carbonate solution and the aqueous layer extracted w... | COC(=O)COc1ccc(CCNCC(OC)c2cccc(Cl)c2)cc1 | null | null | null |
1,473,286 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[N:22]1[CH... | Cc1ccc(N2CCNCC2)c(C)c1 | Cc1cc([N+](=O)[O-])ccc1C(=O)O | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | null | 2-Methyl-4-nitrobenzoic acid (500 mg), 1-(2,4-dimethylphenyl)piperazine (523 mg) and 1-hydroxybenzotriazole 1 hydrate (373 mg) were dissolved in N,N-dimethylformamide (13 mL), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (531 mg) was added, and the mixture was stirred at room temperature. Water was adde... | Cc1ccc(N2CCN(C(=O)c3ccc([N+](=O)[O-])cc3C)CC2)c(C)c1 | null | 79.4 | null |
73,380 | ord_dataset-10f2568b472a4cabb35c3f313a159005 | null | 1980-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C([O:12][C:13](=O)[CH:14]([N:16]=[C:17]=[O:18])[CH3:15])C>>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]2[C:13](=[O:12])[CH:14]([CH3:15])[NH:16][C:17]2=[O:18])[CH:6]=[CH:7][C:8]=1[F:9] | Nc1ccc(F)c(Cl)c1 | CCOC(=O)C(C)N=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2.91 g (20 mmol) of 3-chloro-4-fluoroaniline and 3.01 g (21 mmol) of 2-isocyanato-propionic acid ethyl ester was maintained at 130°-140° C. for 91/2 hours. The resulting product was crystallized from chloroform/methanol to yield 3-(3-chloro-4-fluorophenyl)-5-methyl-hydantoin, m.p. 174°-175.5° C. | CC1NC(=O)N(c2ccc(F)c(Cl)c2)C1=O | null | null | null |
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