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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
337,676 | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | null | 1996-01-01T00:09:00 | true | [Li]CCCC.[CH3:6][N:7]1[CH:11]=[CH:10][S:9][CH2:8]1.CN(P(N(C)C)(N(C)C)=O)C.[CH3:23][N:24]1[N:28]=[N:27][C:26]([C:29]2[CH:39]=[C:38]([CH3:40])[C:32]([O:33][CH2:34][CH2:35][CH2:36]Br)=[C:31]([CH3:41])[CH:30]=2)=[N:25]1.[Cl-].[NH4+]>C1COCC1>[CH3:6][N:7]1[CH:11]=[C:10]([CH2:36][CH2:35][CH2:34][O:33][C:32]2[C:31]([CH3:41])=[... | Cc1cc(-c2nnn(C)n2)cc(C)c1OCCCBr | CN1C=CSC1 | null | [Cl-] | [Li]CCCC | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)P(=O)(N(C)C)N(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | -78 | 0.25 | n-BuLi (2.5M, 1.33 ml, 3.33 mmol) was added slowly at -78° C. to a solution of 3-methyl-thiazole (300 mg, 3.03 mmol) in 8 ml of THF under nitrogen. After stirring at -78° C. for 15 min, HMPA (1.08 g, 6.06 mmol) was added and the resulting mixture was stirred for 10 min. To the above mixture was added at -78° C. 3-[4-(2... | Cc1cc(-c2nnn(C)n2)cc(C)c1OCCCC1=CN(C)CS1 | null | 27.7 | null |
305,053 | ord_dataset-180e296d6d6245638d4d22a59120ea01 | null | 1995-01-01T00:02:00 | true | Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:25])[CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[C:21]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(=[O:25])[CH2:22][CH2:23][CH3:24] | NCCCSc1ccncc1 | CCCC(=O)Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | To a solution of 700 mg (2.90 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 1.62 ml (11.6 mmol) of triethylamine in 30 ml of methylene chloride was added 0.36 ml (3.48 mmol) of butyryl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixt... | CCCC(=O)NCCCSc1ccncc1 | null | 91.1 | null |
589,785 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH3:15])[C:11]([C:20]([F:23])([F:22])[F:21])=[CH:10][C:9]=1[NH2:24])([CH3:4])([CH3:3])[CH3:2].C([O:30][C:31](=O)[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[O:45][N:44]=[C:43]([CH3:46])[CH:42]=2)[CH:36]=1)=[O:34... | CC(C)CN(C)c1cc(NC(=O)OC(C)(C)C)c(N)cc1C(F)(F)F | Cc1cc(-c2cccc(C(=O)CC(=O)OC(C)(C)C)c2)on1 | null | null | null | null | null | null | null | 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-amino-5-(isobutyl-methyl-amino)-4-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester (Example J36) (360 mg, 1.0 mmol) and 3-[3-(3-methyl-isoxazol-5-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester (Example K4) (302 mg, 1.0 mmol) according to the general procedure M. Obtained... | Cc1cc(-c2cccc(C(=O)CC(=O)Nc3cc(C(F)(F)F)c(N(C)CC(C)C)cc3NC(=O)OC(C)(C)C)c2)on1 | null | null | null |
62,824 | ord_dataset-9240b22758dd4f9e981f9ad2d5394155 | null | 1980-01-01T00:02:00 | true | [C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1>C1C=CC=CC=1>[N:8]1([CH:3]=[CH:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH2:12][CH2:11][CH2:10][CH2:9]1 | C#CC(=O)OCC | C1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 8 | A solution of 29.43 g of ethyl propiolate (0.30 mol) in 200 ml of benzene was held at 25° in a water bath with magnetic stirring. A solution of 21.34 g of pyrrolidine in 50 ml of benzene was added dropwise over a period of 45 minutes, during which time the temperature rose to 35°. The clear brown solution was stirred o... | CCOC(=O)C=CN1CCCC1 | null | 69 | null |
432,658 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [C:1]([C:3]1[C:4]([C:25]([F:28])([F:27])[F:26])=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[Cl:24])[C:7]=1[N:8]=[CH:9]OCC)#[N:2].[BH4-].[Na+]>CO>[C:1]([C:3]1[C:4]([C:25]([F:27])([F:28])[F:26])=[N:5][N:6]([C:13]2[C:14]([Cl:24])=[CH:15][C:16]([C:20]([F:22])([F:21])[F:23])... | CCOC=Nc1c(C#N)c(C(F)(F)F)nn1-c1c(Cl)cc(C(F)(F)F)cc1Cl | null | null | [BH4-] | [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 suspension of 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneamino-3-trifluoromethylpyrazole (1.0 g) in methanol (10 ml) stirred at room temperature was added sodium borohydride (0.17 g). After 2 hours an additional 0.17 g of sodium borohydride was added, and another 0.34 g added after 1 hours. ... | CNc1c(C#N)c(C(F)(F)F)nn1-c1c(Cl)cc(C(F)(F)F)cc1Cl | null | null | null |
43,060 | ord_dataset-4c8627b52d564809adb9b494879c07c0 | null | 1978-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]=[C:17]([O:20][CH2:21][CH3:22])[CH2:18]Br)=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[NH3:23]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:16]=[C:17]([O:20][CH2:21][CH3:22])[CH2:18][N:23]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]=2[CH:15]=1 | CCOC(CBr)=Nc1ccc(Cl)cc1C(=O)c1ccccc1 | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of a solution of 0.38 part of 5-chloro-2-(2-bromo-1-ethoxyethylideneamino)benzophenone in 8 parts by volume of methylenechloride and 2 parts by volume of liquid ammonia is stirred in a sealed vessel at room temperature for 1 hour, followed by evaporation at room temperature to remove the ammonia. The resultan... | CCOC1=Nc2ccc(Cl)cc2C(c2ccccc2)=NC1 | null | null | null |
1,294,962 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:19][C:20]2[CH2:21][NH:22][CH2:23][CH2:24][C:25]=2[N:26]=1)=[O:17].[CH3:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>C1COCC1>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:19... | Cc1ccc(S(=O)(=O)Cl)cc1 | Nc1ccccc1NC(=O)c1nc2c(s1)CNCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 0 | 2 | Triethyl amine (1.0 eq) was added to solution of N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide obtained in step VIII of example I (1.0 mmol) in 10 mL THF. The solution was cooled to 0° C. 4-Methyl-benzenesulfonyl chloride (1.0 mmol) was added slowly with continuous stirring. Reaction mi... | Cc1ccc(S(=O)(=O)N2CCc3nc(C(=O)Nc4ccccc4N)sc3C2)cc1 | null | null | null |
1,199,035 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:14])=[CH:8]2.C[N:16](C=O)C>>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([NH2:16])[C:9]([CH3:14])=[CH:8]2 | CN(C)C=O | COc1ccc2[nH]c(C)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 | 0 | 0.5 | A suspension of NaH (1.25 g, 51 mmol, 60% in mineral oil) in DMF (47 mL) at 0° C. is treated with 5-methoxy-2-methylindole (500 mg, 3.1 mmol) and stirred at 0° C. for 0.5 h. The mixture is treated with HOSA (1.92 g, 17.0 mmol) portion wise and warmed to rt over 2 h. The mixture is then poured over ice, and extracted wi... | COc1ccc2c(c1)cc(C)n2N | null | null | null |
270,478 | ord_dataset-a20aed058d7b40bc81fdf50bc5b03f97 | null | 1993-01-01T00:06:00 | true | [NH:1]=[C:2]1[NH:6][C:5]([C:11]([F:14])([F:13])[F:12])([C:7]([F:10])([F:9])[F:8])[C:4](=[C:15]([F:20])[C:16]([F:19])([F:18])[F:17])[S:3]1.C(N(CC)CC)C.[N+:28]([C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](Cl)=[O:35])([O-:30])=[O:29]>C1(C)C=CC=CC=1>[N+:28]([C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([NH... | N=C1NC(C(F)(F)F)(C(F)(F)F)C(=C(F)C(F)(F)F)S1 | O=C(Cl)c1cccc([N+](=O)[O-])c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 103 | 3 | In toluene (40 ml) were dissolved 2-imino-4,4-bis(trifluoromethyl)-5-(tetrafluoroethylidene)-1,3-thiazolidine (2.0 g) and triethylamine (1.0 ml), and a solution of 3-nitrobenzoyl chloride (1.3 g) dissolved in toluene (10 ml) was gradually added thereto under cooling and the mixture was stirred at 103° C. for 3 hours. | O=C(NC1=NC(C(F)(F)F)(C(F)(F)F)C(=C(F)C(F)(F)F)S1)c1cccc([N+](=O)[O-])c1 | null | null | null |
762,555 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [CH:1]1([N:6]2[C:11]3=[N:12][C:13](S(C)=O)=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:20]=3[F:29])[C:7]2=[O:30])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:31][CH2:32][C@H:33]([OH:38])[C@@H:34]([OH:37])[CH2:35][OH:36]>>[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:31][CH2:32... | NC[C@H](O)[C@@H](O)CO | COc1cc(OC)c(F)c(N2Cc3cnc(S(C)=O)nc3N(C3CCCC3)C2=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1-Cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-([S,S]-2,3,4-trihydroxy-butylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as in Example 2 using 0.40 g (0.92 mmol) 1-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.33 g (2.76 mmol)... | COc1cc(OC)c(F)c(N2Cc3cnc(NC[C@H](O)[C@@H](O)CO)nc3N(C3CCCC3)C2=O)c1 | null | null | null |
858,528 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | C(OC(=O)NC1C=CC(N2C=[C:20]([S:22][CH3:23])[N:19]=N2)=C(F)C=1)C1C=CC=CC=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:36][C:37]1[CH:38]=[C:39]([N:49]2[CH2:53][C@H:52]([CH2:54][OH:55])[O:51][C:50]2=[O:56])[CH:40]=[CH:41][C:42]=1[N:43]1[CH:47]=NC(C)=[N:44]1>>[F:36][C:37]1[CH:38]=[C:39]([N:49]2[CH2:53][C@H:52]([CH2:54][OH:55])[O:5... | Cc1ncn(-c2ccc(N3C[C@H](CO)OC3=O)cc2F)n1 | CSc1cn(-c2ccc(NC(=O)OCc3ccccc3)cc2F)nn1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | [3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl] carbamic acid benzyl ester (Intermediate 49) (27.4 g, 76.5 mmol), LiHMDS (1M in THF, 91 ml) and R-(−)-glycidyl butyrate (11.5 g, 79.7 mmol) were reacted following the procedure for Intermediate 25 to give the crude title compound (19.4 g), which was used without... | CSc1cn(-c2ccc(N3C[C@H](CO)OC3=O)cc2F)nn1 | null | null | null |
1,028,134 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[O:20])[S:9][C:10]=1[C:11]([C:13]1[CH:17]=[CH:16][NH:15][CH:14]=1)=[O:12].[H-].[Na+].[CH3:29]I.O>CN(C=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:18][C:19]([C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH... | O=C(Nc1nc(-c2ccco2)c(C(=O)c2cc[nH]c2)s1)c1ccncc1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 2 | Compound 353 (105 mg, 0.288 mmol) was dissolved in DMF (1.4 mL), and 55% sodium hydride (25.3 mg, 0.576 mmol) and methyl iodide (0.0179 mL, 0.288 mmol) were added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The org... | Cn1ccc(C(=O)c2sc(NC(=O)c3ccncc3)nc2-c2ccco2)c1 | null | 89 | null |
1,201,285 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.[F:15][C:16]([F:29])([F:28])[C:17]1[CH:18]=[C:19]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[NH2:20]>>[F:15][C:16]([F:28])([F:29])[C:17]1[CH:18]=[C:19]([NH:20][C:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[C... | Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | O=C(O)c1ccc2ccccc2c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using 1-hydroxynaphthalene-2-carboxylic acid and 3,5-bis(trifluoromethyl)aniline as the raw materials, the same operation as the example 16 gave the title compound. | O=C(Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1ccc2ccccc2c1O | null | 65.5 | null |
539,984 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH:18]1([C:24](Cl)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>>[CH:18]1([C:24]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[NH:9][C:10]4[CH:16]=[CH:15][C:14]([NH:17][C:24]([CH:18]5[CH2:23][CH2:22][... | O=C(Cl)C1CCCCC1 | Nc1ccc(-c2nc3cc(N)ccc3[nH]2)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 | 2-(N-Cyclohexylcarbanoyl-4′-aminophenyl)-6-(cyclohexylcarbanoylamino)-benzimidazole was prepared by Method A from 2-(4-aminophenyl)-6-aminobenzimidazole (0.195 g, 0.87 mmole) and cyclohexylcarbonyl chloride (0.291 ml, 0.319 g, 2.175 mmole). The resulting solid (76.7 mg) was purified by preparative HPLC. | O=C(Nc1ccc(-c2nc3cc(NC(=O)C4CCCCC4)ccc3[nH]2)cc1)C1CCCCC1 | null | null | null |
1,054,680 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH2:1]([N:8]1[C:12](=[O:13])[N:11]([C:14]2[CH:15]=[N:16][N:17]([CH2:19][C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])[CH:18]=2)[C:10](=[O:27])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:29][CH2:30][CH3:31]>>[CH2:1]([N:8]1[C:12](=[O:13])[N:11]([C:14]2[CH:15]=[N:16][N:17]([CH2:19][C:20]3[C:21]([CH3:26... | CCCBr | Cc1noc(C)c1Cn1cc(-n2c(=O)[nH]n(Cc3ccccc3)c2=O)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared as in example 10-91 from 1-benzyl-4-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1,2,4-triazolidine-3,5-dione (example 10-9a) and 1-bromopropane. Yield: 38%. MS M+H calculated 409.19; found 409.2. The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.06 μM. | CCCn1c(=O)n(-c2cnn(Cc3c(C)noc3C)c2)c(=O)n1Cc1ccccc1 | null | 38 | null |
495,681 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2[NH2:19])[CH:7]=1.[F:20][C:21]([F:33])([F:32])[C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>CCOCC>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F... | Nc1cc(C(F)(F)F)ccc1Oc1cncc(Cl)c1 | O=S(=O)(Cl)c1ccc(C(F)(F)F)cc1 | 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 | null | Using the method of Example 17.4, 4-(3-chloro-5-pyridyloxy)-3-aminobenzotrifluoride (0.4 g) and 4-trifluoromethylbenzenesulfonyl chloride ((0.339 g ) were combined to provide, after trituration with ether, the title sulfonamide (0.198 g) which was obtained as a crystalline solid. mp 169-171° C. | O=S(=O)(Nc1cc(C(F)(F)F)ccc1Oc1cncc(Cl)c1)c1ccc(C(F)(F)F)cc1 | null | null | null |
1,350,609 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>C1COCC1>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[N:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1)([O-:14])=[O:13] | C1CSCCN1 | O=[N+]([O-])c1cc(C(F)(F)F)ccc1F | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 48 | To a solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (7.00 g, 33.48 mmol) in THF (250 ml) at room temperature was added thiomorpholine (3.45 g, 33.48 mmol) and sodium bicarbonate (3.66 g, 43.52 mmol). The vessel was purged with nitrogen and stirred at room temperature for 48 hours. After removal of solvent unde... | O=[N+]([O-])c1cc(C(F)(F)F)ccc1N1CCSCC1 | null | null | null |
72,906 | ord_dataset-10f2568b472a4cabb35c3f313a159005 | null | 1980-01-01T00:11:00 | true | [C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1.F>O>[C:9]([O:7][C:1]1[CH:6]=[CH:5][C:4]([C:13]([C:12]2[CH:11]=[CH:10][C:9]([O:8][C:13](=[O:15])[CH3:12])=[CH:17][CH:16]=2)=[O:15])=[CH:3][CH:2]=1)(=[O:8])[CH3:10] | O=C(O)c1ccc(O)cc1 | Oc1ccccc1 | null | F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | 45.5 g (0.52 mole) of phenol, 69.0 g (0.50 mole) of 4-hydroxybenzoic acid, and 500 mL of hydrogen fluoride were heated together for 6 hr under autogenous pressure in an autoclave. Then the contents were mixed in excess water to precipitate a pink solid. Yield was 99 g (92.5%). The crude product was acetylated directly,... | CC(=O)Oc1ccc(C(=O)c2ccc(OC(C)=O)cc2)cc1 | null | 151.5 | null |
1,121,852 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.[Cl:23][C:24]1[CH:25]=[C:26]([C:49]2[CH:54]=[CH:53][C:52]([C:55]([N:57]3[CH2:62][CH2:61][CH:60]([C:63]([F:66])([F:65])[F:64])[CH2:59][CH2:58]3)=[O:56])=[CH:51][CH:50]=2)[CH:27]=[C:28]([Cl:48])[C:29]=1[CH2:30][C@@H:31]1[CH2:35][CH2:34][N:33]([C@H:36]2[CH2:41][CH2:40][C@H:39](OS(C)... | CS(=O)(=O)O[C@H]1CC[C@H](N2CC[C@@H](Cc3c(Cl)cc(-c4ccc(C(=O)N5CCC(C(F)(F)F)CC5)cc4)cc3Cl)C2=O)CC1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | 80 | 12 | Dissolve tetrabutylammonium fluoride trihydrate (0.436 g, 1.36 mmol) in 5 ml of acetonitrile. Add water (0.05 ml. 2.72 mmol) and stir for 10 minutes. Add trans-methanesulfonic acid 4-{(R)-3-[3,5-dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-2-oxo-pyrrolidin-1-yl}-cyclohexyl ester (0.458 g, ... | O=C(c1ccc(-c2cc(Cl)c(C[C@@H]3CCN(C4CC=CCC4)C3=O)c(Cl)c2)cc1)N1CCC(C(F)(F)F)CC1 | null | null | null |
851,659 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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=CC=2)(C2C=CC=CC=2)C2C=CC=C... | OB(O)c1ccccc1 | COc1cc(Cl)ccc1CBr | 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 | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | 1-Bromomethyl-4-chloro-2-methoxy-benzene (50 mg, 0.21 mmol), phenyl boronic acid (28 mg, 0.23 mmol), Pd(PPh3)4 (24 mg, 0.021 mmol) and K2CO3 (87 mg, 0.63 mmol) were combined in dioxane, purged with N2, and heated to reflux for 16 hours. The mixture was then partitioned between ethyl acetate and water. The organic layer... | COc1cc(Cl)ccc1Cc1ccccc1 | null | 18.4 | null |
49,233 | ord_dataset-0bb2e99daa66408fb8dbd6a0781d241c | null | 1978-01-01T00:12:00 | true | [CH3:1][O:2][C:3](=[O:42])[C@H:4]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:5][C:6](=[O:37])[CH2:7][NH:8][C:9](=[O:36])[C@H:10]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[NH:11][C:12](=[O:27])[C@H:13]([CH2:25][OH:26])[NH:14]C(OCC1C=CC=CC=1)=O.[ClH:43]>CO.[Pd]>[ClH:43].[CH3:1][O:2][C:3](=[O:42])[C@H:4](... | COC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)OCc1ccccc1 | null | null | [Pd] | Cl | 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 consisting of 2.4 g. of N-benzyloxycarbonyl-L-seryl-L-tyrosylglycyl-L-leucine methyl ester, 60 ml. of methanol, 240 mg. of 5% palladium-on-carbon, and 5.4 ml. of 1.26 N hydrogen chloride in methanol is hydrogenated at one atmosphere and 25° C. for one hour. The mixture is then filtered to remove the catalyst,... | COC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](N)CO | null | null | null |
73,665 | ord_dataset-10f2568b472a4cabb35c3f313a159005 | null | 1980-01-01T00:11:00 | true | C[N:2]([CH3:17])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=O.N[C:19]1[C:23]([C:24]#[N:25])=C[NH:21][N:20]=1>C(O)(=O)C>[F:16][C:13]([F:14])([F:15])[C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[N:21]3[N:20]=[CH:19][C:23]([C:24]#[N:25])=[C:17]3[N:2]=[CH:3][CH:4]=2)[CH:8]=1 | CN(C)C=CC(=O)c1cccc(C(F)(F)F)c1 | N#Cc1c[nH]nc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3.15 g. of 3-dimethylamino-3'-(trifluoromethyl)acrylophenone and 1.40 g. of 3-aminopyrazole-4-carbonitrile in 25 ml. of glacial acetic acid is refluxed for 6 hours. The mixture is evaporated and the residue is treated as described in Example 1, giving the desired product, m.p. 144°-145° C. | N#Cc1cnn2c(-c3cccc(C(F)(F)F)c3)ccnc12 | null | null | null |
674,933 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | [CH2:1]([CH:5]([C:9](O)=O)[C:6]([OH:8])=[O:7])[CH2:2][CH2:3][CH3:4].N1CCCCC1.C=O>C(O)C>[CH2:1]([C:5](=[CH2:9])[C:6]([OH:8])=[O:7])[CH2:2][CH2:3][CH3:4] | CCCCC(C(=O)O)C(=O)O | null | null | C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | CCO | null | null | null | null | null | null | null | null | null | 80 | 8 | To a solution of n-butylmalonic acid (17.2 g, 107 mmol) in ethanol (200 ml) was added piperidine (12.76 ml, 129 mmol) and 37% aq. formaldehyde (40.3 ml, 538 mmol). The solution was heated to 80° C. during which time a precipitate appeared and gradually redissolved over 1 hour. The reaction mixture was stirred at 80° C.... | C=C(CCCC)C(=O)O | null | 97.5 | null |
1,697,090 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [C:1]([NH:4][CH2:5][CH2:6][N:7]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[N:9]2[C:17](=[O:46])[C:18]3[N:19]([CH:21]=[C:22]([C:34]([NH:36][CH2:37][C:38]4[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:39]=4[F:45])=[O:35])[C:23](=[O:33])[C:24]=3[O:25]CC3C=CC=CC=3)[CH2:20][CH:8]12)(=[O:3])[CH3:2]>[Pd]>[C:1]([NH:4... | CC(=O)NCCN1CC2CCCCC2N2C(=O)c3c(OCc4ccccc4)c(=O)c(C(=O)NCc4ccc(F)cc4F)cn3CC12 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | racemic-4aS,6aS,14aS)-6-[2-(Acetylamino)ethyl]-N-[(2,4-difluorophenyl)methyl]-12-hydroxy-11,13-dioxo-1,2,3,4,4a,5,6,6a,7,11,13,14a-dodecahydropyrido[1′,2′:4,5]pyrazino[1,2-a]quinazoline-10-carboxamide. In a manner similar to that described in example Z-35, from racemic-N-[2-({[(1S,2S)-2-aminocyclohexyl]methyl}amino)eth... | CC(=O)NCCN1CC2CCCCC2N2C(=O)c3c(O)c(=O)c(C(=O)NCc4ccc(F)cc4F)cn3CC12 | null | null | null |
804,245 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:9]=2)[C:4](=[O:19])[CH2:3]1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:4](=[O:19])[CH2:3][C:2]3([CH3:20])[CH3:1])=[CH:25][CH:24]... | COc1ccc(B(O)O)cc1 | CC1(C)CC(=O)c2ccc(OS(=O)(=O)C(F)(F)F)cc21 | null | null | null | null | null | null | null | 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 trifluoro-methanesulfonic acid 3,3-dimethyl-1-oxo-indan-5-yl ester and 4-methoxyphenyl boronic acid according to the procedure described in example 21. MS (ES) m/z 267.1. HRMS: calcd for C18H18O2+H+, 267.13796; found (ESI, [M+H]+), 267.1373. | COc1ccc(-c2ccc3c(c2)C(C)(C)CC3=O)cc1 | null | null | null |
673,703 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | [F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[NH:12][C:11]3=[O:18])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:24][C:25]([NH2:27])=[O:26].O>O1CCCC1>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([CH2:24][C:2... | O=C1NC(=O)c2cc(OCc3ccc(F)cc3)ccc21 | NC(=O)CBr | null | [H-] | [Na+] | 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 | 25 | 3 | A mixture of 5-(4-fluoro-benzyloxy)-isoindole-1,3-dione (100 mg, 0.37 mmol), sodium hydride (55% in mineral oil, 18 mg, 0.42 mmol) and 2-bromoacetamide (61 mg, 0.44 mmol) in dry tetrahydrofuran (5 mL) at 0° C. was stirred at room temperature for 3 h and then heated at 50° C. for 1 h. After cooling to 0° C., water (2 mL... | NC(=O)CN1C(=O)c2ccc(OCc3ccc(F)cc3)cc2C1=O | null | 64.2 | null |
669,419 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [F:1]/[C:2](=[C:13](/[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH2:26][CH2:27][CH3:28])[O:21][C:20]([CH3:30])([CH3:29])[CH:19]=[C:18]2[CH:31]([CH3:33])[CH3:32])\[CH3:14])/[CH:3]=[CH:4]/[C:5](/[CH3:12])=[CH:6]/[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C(O)C.C1COCC1>[F:1]/[C:2](=[C:13](/[C:15]1[CH:16]=[C:17]2[C:22](=[CH... | CCCOc1cc2c(cc1/C(C)=C(F)\C=C\C(C)=C\C(=O)OCC)C(C(C)C)=CC(C)(C)O2 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | Following General Procedure G, a solution of ethyl (2E,4E,6E)-6-fluoro-7-(4-isopropyl-2,2-dimethyl-7-propoxy-2H-chromen-6-yl)-3-methyl-octa-2,4,6-trienoate (Compound 112, 73 mg, 0.16 mmo) in ethanol and THF was hydrolyzed with NaOH to yield the title compound as a yellow solid after recrystallized from acetonitrile. | CCCOc1cc2c(cc1/C(C)=C(F)\C=C\C(C)=C\C(=O)O)C(C(C)C)=CC(C)(C)O2 | null | null | null |
203,223 | ord_dataset-19e5fc80c1554f4f8641c835e055f02b | null | 1990-01-01T00:01:00 | true | [C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[Li]CCCC.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[C:38]([CH3:43])[CH:37]=2)=[C:25]([C:30]2[N:34]([CH3:35])[N:33]=[N:32][N:31]=2)[CH:26]=[CH:27][CH:28]=[O:29])=[CH:20][C:19]=1[CH3:44]>O1CCCC1.CCCCCC>[F:17][C:1... | Cc1cc(C(=C(C=CC=O)c2nnnn2C)c2ccc(F)c(C)c2)ccc1F | CCOC(=O)CC(C)=O | null | [H-] | [Li]CCCC | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCC | null | null | null | null | null | null | null | null | null | -78 | 0.25 | A solution of the dianion of ethyl acetoacetate (1.42 mL, 11.1 mmoles) in dry tetrahydrofuran (15 mL) was generated as described in Example 10 using 450 mg (11.3 mmoles) of NaH (60% in mineral oil) and 4.5 mL (11.1 mmoles) of 2.5M n-BuLi in hexane at 0° C. under argon. The orange dianion solution, after being chilled t... | CCOC(=O)CC(=O)CC(O)C=CC(=C(c1ccc(F)c(C)c1)c1ccc(F)c(C)c1)c1nnnn1C | null | 48.6 | null |
8,688 | ord_dataset-ad879e603f9440f6bfb7fbd18e5e8761 | null | 1976-01-01T00:06:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[CH3:13]N(N=O)C(N)=O.[OH-].[K+]>COCCOC.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:9][CH3:13])=[O:8])([O-:3])=[O:2] | O=C(O)c1cccc([N+](=O)[O-])c1 | CN(N=O)C(N)=O | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | O | null | null | null | null | null | null | null | null | null | null | null | 1.00 grams (6 millimoles) of m-nitrobenzoic acid and 2.4 grams (2.4 millimoles) of N-methyl,N-nitrosourea were dissolved in 25 milliliters of a 5:1 mixture of 1,2-dimethoxyethane and water. 40 milliliters of 0.6 N potassium hydroxide was added in a dropwise manner while the mixture was held at 0°C. in an ice bath. The ... | COC(=O)c1cccc([N+](=O)[O-])c1 | null | 149.5 | null |
416,591 | ord_dataset-1cb9d78632144c5f8acfc3e9ff388678 | null | 1998-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:15]2[CH2:17][O:16]2)[CH2:10][C:11]([O:13]C)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>FC(F)(F)CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:17][N:19]([CH3:18])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:16][C:11](=[O:13])[CH2:1... | COC(=O)CC(c1ccc(Cl)c(Cl)c1)C1CO1 | CNc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | OCC(F)(F)F | null | null | null | null | null | null | null | null | null | null | 23 | 6 | Treat a solution of the product of step 2 (368 mg, 1.34 mmol) in 2,2,2 trifluoroethanol (1 mL) with N-methyl aniline (217 μL, 2.01 mmol, 1.5 eq) and stir for 6 h at 23° C. followed by 6 h at 80° C. Cool to 23° C., concentrate in vacuo and purify by silica gel chromatography (column: 3.5×12 cm; eluant: hexane:EtOAc (4:1... | CN(CC1OC(=O)CC1c1ccc(Cl)c(Cl)c1)c1ccccc1 | null | 97 | null |
903,409 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=2[CH3:22])=[C:6]([CH2:8][C:9](O)=O)[CH:7]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-:37].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][CH2:13][C:14]3[C:15]([CH3:22])=[C:16]([O:20][CH3:21])[CH:17]=[CH:... | [OH-] | COc1cccc(CCc2ccc(Br)cc2CC(=O)O)c1C | null | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | [Na+] | 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 | 90 | null | To a stirred suspension of 5-bromo-2-[2-(3-methoxy-2-methyl-phenyl)-ethyl]-phenylacetic acid (11) (4.38 g; 12.06 mmol) in toluene (20 mL), was added phosphorous pentoxide (6.0 g; 42.2 mmol). The mixture was heated at 90° C. for 16 hours. The mixture was cooled, treated with 1.0 N solution of sodium hydroxide and extrac... | COc1ccc2c(c1C)CCc1ccc(Br)cc1CC2=O | null | 55 | null |
838,245 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[C:12](=O)[NH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[C:9]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)=[N:10][N:1... | COc1ccc2c(-c3ccc(C)c(C)c3)n[nH]c(=O)c2c1 | O=P(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 | This compound is obtained according to the procedure described in 1.3. by reacting 4-(3,4-dimethylphenyl)-7-methoxy-2H-phthalazin-1-one with phosphoryl chloride. | COc1ccc2c(-c3ccc(C)c(C)c3)nnc(Cl)c2c1 | null | null | null |
382,204 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CCOCC1)C.ClC(OCC(C)C)=O.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1>[CH2:33]([NH:40][C:14](=[O:16])[C@H:9]([C@H:10]([CH2:12][CH3:13])[CH3:11])[NH:8][C:6]([O:5][C:1]([CH3:... | CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)O | NCc1ccccc1 | null | CC(C)COC(=O)Cl | CCN1CCOCC1 | 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 | -5 | null | Into a 500 mL round bottomed flask equipped with a magnetic stirrer was added N-(tert-butoxycarbonyl)-L-isoleucine (22.53 g, 97.39 mmol, 1.0 eq) and THF (300 mL). The solution was stirred until homogeneous, cooled to -5° C., and treated with N-ethylmorpholine (14.23 mL, 12.88 g, 112.0 mmol, 1.15 eq). The solution was s... | CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)NCc1ccccc1 | null | 95.9 | null |
589,752 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][C:9]=1[NH2:21])([CH3:4])([CH3:3])[CH3:2].[N:23]1([C:28]2[CH:29]=[C:30]([C:34]3[O:39]C(C)(C)[O:37][C:36](=O)[CH:35]=3)[CH:31]=[CH:32][CH:33]=2)[CH:27]=[CH:26][N:25]=[CH:24]1>>[C:1]([O:5][C:6](=[O:22]... | CN(C)c1cc(NC(=O)OC(C)(C)C)c(N)cc1C(F)(F)F | CC1(C)OC(=O)C=C(c2cccc(-n3ccnc3)c2)O1 | null | null | null | null | null | null | null | 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-amino-5-dimethylamino-4-trifluoromethyl-phenyl)-carbamic acid tert.-butyl ester (Example J6) and 6-(3-imidazol-1-yl-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one (Example L3) according to the general procedure M. Obtained as an orange oil (238 mg). | CN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(-n3ccnc3)c2)cc1C(F)(F)F | null | null | null |
279,017 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | I[C:2](=[CH2:16])[CH2:3][CH:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[OH:5].[OH-].[Na+].Cl>CN(C)C=O>[C:6]1([CH:4]([CH2:3][C:2]#[CH:16])[OH:5])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1 | C=C(I)CC(O)c1cccc2ccccc12 | null | null | Cl | [Na+] | [OH-] | 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 | 6 | 5.00 Grams of 2-iodoallyl-α-naphthylcarbinol were disolved in 50 g of dimethylformamide, and 1.23 g of sodium hydroxide in a flake form were added. The mixture was stirred at room temperature for 6 hours. After the reaction was completed the reaction mixture was neutralized with concentrated hydrochloric acid, insolubl... | C#CCC(O)c1cccc2ccccc12 | null | null | null |
1,337,681 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:15])C)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[CH:27]2[CH:22]([C:23]3([CH3:29])[O:28][CH:26]2[CH2:25][CH2:24]3)[C:21](=[O:30])[CH:20]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH2:13][O:15][C:19]3[CH:27]4[CH:22]([C:23]5([CH3:29]... | CC(O)c1cnc(-c2ccc(Cl)cc2)s1 | CC12CCC(O1)C1C(Cl)=CC(=O)C12 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.08 | To a solution of 1-[2-(4-chloro-phenyl)-thiazol-5-yl]ethanol (264 mg, 1.1 mmol) in tetrahydrofuran (5 ml) is added in one portion the sodium hydride (60% dispersion in mineral oil, 44 mg, 1.1 mmol). The reaction mixture is stirred for five minutes at room temperature and 5-Chloro-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]d... | CC12CCC(O1)C1C(OCc3cnc(-c4ccc(Cl)cc4)s3)=CC(=O)C12 | null | 96.1 | null |
1,112,623 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][NH2:25])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[CH2:27]([N:34]=[C:35]=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8... | O=C=NCc1ccccc1 | CCOC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN)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 | Prepared according to the procedure described in Example 95, Step 1, using the following starting materials: (2′-aminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester and benzyl isocyanate. | CCOC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CNC(=O)NCc2ccccc2)c1 | null | null | null |
479,141 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [CH2:1]1[O:12][C:11]2[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][C:3]=2[O:2]1.[Cl:13][C:14]1[N:15]=[C:16](Cl)[C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[S:20][C:18]=2[N:19]=1>>[Cl:13][C:14]1[N:15]=[C:16]([NH:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][C:11]3[O:12][CH2:1][O:2][C:3]=3[CH:4]=2)[C:17]2[CH:22]=[C:21]... | NCCc1ccc2c(c1)OCO2 | FC(F)(F)c1cc2c(Cl)nc(Cl)nc2s1 | null | null | null | null | null | null | null | 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 procedure of Example 1, the reaction of 3,4-methylenedioxyphenethylamine with 2,4-dichloro-6-trifluoromethyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-trifluoromethyl-4-(3,4-methylenedioxyphenethylamino)-thieno-[2,3-d]-pyrimidine. | FC(F)(F)c1cc2c(NCCc3ccc4c(c3)OCO4)nc(Cl)nc2s1 | null | null | null |
1,000,735 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.CN(C=O)C.[C:21]([C:23]1[CH:24]=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1)#[N:22]>>[CH3:15][N:13]([CH2:12][C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:29]([C:25]1[C... | N#Cc1cccc(S(=O)(=O)Cl)c1 | COc1ccc2[nH]ccc2c1CN(C)C | null | null | null | 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 | 0.25 | To a solution of 1-(5-methoxy-1H-indol-4-yl)-N,N-dimethylmethanamine (15 mg, 0.07 mmol; Intermediate 97) in DMF (1 mL) NaH (4 mg, 0.15 mmol) was added at rt. The reaction mixture was stirred at rt for 15 min and 3-cyanobenzenesulphonyl chloride (22 mg, 0.11 mmol) was added. The reaction mixture was allowed to stir at r... | COc1ccc2c(ccn2S(=O)(=O)c2cccc(C#N)c2)c1CN(C)C | null | 15.5 | null |
1,533,027 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=O)[NH:5][C:6]=1[CH2:7][CH3:8].S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:24][CH:25]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=2)=[CH:19][C:18]=1[CH3:32]>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:24][CH:25]=[C:26]([C:2... | COC(=O)c1coc(-c2ccc(N)c(C)c2)n1 | CCc1[nH]c(C(=O)O)nc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (0.12 g, 0.69 mmol), thionyl chloride (4 mL), methyl 4-amino-3-methylphenyl)-1,3-oxazole-4-carboxylate obtained in Example (109e) (0.23 g, 0.95 mmol) and pyridine (5 mL), to obtain 135 mg of the title compound as ... | CCc1[nH]c(C(=O)Nc2ccc(-c3nc(C(=O)OC)co3)cc2C)nc1Cl | null | 50.3 | null |
1,733,808 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Cl:1][C:2]1[N:3]=[C:4]([C:7]2[C:15]3[N:11]([C:12]([C:24]4[CH:28]=[CH:27][N:26]([CH3:29])[N:25]=4)=[C:13]4[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[N:16]([CH3:23])[C:14]4=3)[CH2:10][CH2:9][CH:8]=2)[S:5][CH:6]=1>[Pt].C(O)C.C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]2[C:15]3[N:11]([C:12]([C:24]4[CH:28]=[CH:27][N:26]([CH3... | Cn1ccc(-c2c3c(=O)n(C)c(=O)n(C)c3c3n2CCC=C3c2nc(Cl)cs2)n1 | null | null | [Pt] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 168 | A suspension of 10-(4-chlorothiazol-2-yl)-1,3-dimethyl-5-(1-methyl-1H-pyrazol-3-yl)-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (25 mg, 0.058 mmol) and 10% platinum on carbon (12 mg, 6.15 μmol) in ethanol (2.2 ml) and THF (6.6 ml) was stirred under an atmosphere of hydrogen for 7 days. The mixture was filtere... | Cn1ccc(-c2c3c(=O)n(C)c(=O)n(C)c3c3n2CCCC3c2nc(Cl)cs2)n1 | null | null | null |
1,767,115 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[N:11]2[CH:12]=[C:13]([O:16][C@H:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C@@H:20]([NH2:27])[CH2:19][CH2:18]3)[CH:14]=[CH:15][C:10]2=[N:9][N:8]=1.ClC(Cl)(Cl)C[O:31][C:32](=O)[NH:33][C:34]1[N:35]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([O:50][Si](C(C)C)(C(C... | CC(C)[Si](Oc1cc(-n2nc(C(C)(C)C)cc2NC(=O)OCC(Cl)(Cl)Cl)ccc1Cl)(C(C)C)C(C)C | CN1CCC[C@H]1c1nnc2ccc(O[C@@H]3CC[C@H](N)c4ccccc43)cn12 | null | null | null | null | null | null | null | 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 (193 mg, 76%) was prepared starting from Intermediate E (155 mg, 0.427 mmol) and [5-tert-butyl-2-(4-chloro-3-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester (WO2011/154734A1, which is incorporated herein by reference, 260 mg, 0.436 mmol), using analogous proc... | CN1CCC[C@H]1c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4-c4ccc(Cl)c(O)c4)c4ccccc43)cn12 | null | 76 | null |
439,494 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [CH2:1]([O:3][C:4](=[O:32])[C@@H:5]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:6][NH:7][C:8](=[O:21])[CH2:9][NH:10]C(OCC1C=CC=CC=1)=O)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:32])[C@@H:5]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:24])=[O:25])[CH2:6][NH:7][C... | CCOC(=O)[C@H](CNC(=O)CNC(=O)OCc1ccccc1)NS(=O)(=O)c1ccccc1 | null | 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 | 4 | Protected amine 3-5 (0.47 g, 1.01 mmol) was dissolved in 10 mL EtOH, 10% Pd/C (94 mg) was added, and the reaction was stirred under an H2 balloon. After 4 h, additional 10% Pd/C was added (94 mg), and the reaction was continued for 3 d. The mixture was filtered through Celite, concentrated, and azeotroped with CHCl3, p... | CCOC(=O)[C@H](CNC(=O)CN)NS(=O)(=O)c1ccccc1 | null | null | null |
211,350 | ord_dataset-e0a818f9350b46cdb184d2ac404ede9f | null | 1990-01-01T00:06:00 | true | Br[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)(=O)C>[C:12]1([CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][NH:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:2... | NCc1ccccc1 | BrCCCOCCOCCCc1ccccc1 | 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 | null | 4.5 | [3-[2-(3-Bromopropoxy)ethoxy]propyl]benzene (3.01 g) was added dropwise over 5 min to benzylamine (5.35 g) at 120° under nitrogen. The solution was stirred at 130° for 4.5 h, cooled, diluted with ethyl acetate (200 ml) and washed with 2N hydrochloric acid (150 ml). The aqueous phase was re-extracted with ethyl acetate ... | c1ccc(CCCOCCOCCCNCc2ccccc2)cc1 | null | 78.8 | null |
671,042 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CCOC(C)=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([Br:9])[N:6]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11]... | CC(C)(C)OC(=O)N1CCNCC1 | Nc1ncc(Br)nc1Br | 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 | 120 | null | 2-Amino-3,5-dibromopyrazine (1.26 g, 5.0 mmol) and piperazine-1-carboxylic acid tert-butyl ester (4.64 g, 25 mmol) were placed in a dry RBF and heated with stirring to 120° C. under dry nitrogen. Molten mixture was stirred at this temperature for 6 h and cooled to room temperature. The resulting slurry was diluted with... | CC(C)(C)OC(=O)N1CCN(c2nc(Br)cnc2N)CC1 | null | null | null |
1,753,723 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=1.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>COCCOC.O>[N:10]1([C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:21]3[CH:20]=[CH:19][C:18]([O:17][C:16]([F:15])([F:27])[... | OB(O)c1ccc(OC(F)(F)F)cc1 | N#Cc1cc(Cl)nc(N2CCCC2)c1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | O | null | null | null | null | null | null | null | null | null | 100 | 12 | A solution of nitrile 25A (2.58 g, 12.5 mmol) in DME (90 mL) was added with 4-trifluoromethoxy phenyl boronic acid (2.64 g, 1.0 mol eq,) and NaHCO3 (3.15 g, 3 mol eq,) suspended in water (45 mL). The mixture was degassed under vacuum, then Palladium Tetrakis was added (catalytic amount) and the reaction was stirred at ... | N#Cc1cc(-c2ccc(OC(F)(F)F)cc2)nc(N2CCCC2)c1 | null | 76.8 | null |
1,275,645 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][N:9]=1.C1C=C([Cl:24])C=C(C(OO)=O)C=1>CCOC(C)=O>[Cl:24][C:10]1[CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:13]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=1 | O=C(OO)c1cccc(Cl)c1 | FC(F)(F)c1ccnc(-c2ccccc2Cl)c1 | 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 | null | null | To a solution of 2-(2-chlorophenyl)-4-(trifluoromethyl)pyridine (5.40 g, 21.0 mmol) in EtOAc (100 mL) was added mCPBA (7.25 g, 42.0 mmol) in EtOAc (100 mL) over 30 min and then the mixture was heated at reflux (caution: use shield) for 3 h. The reaction mixture was cooled and then washed twice with sat. aq. NaHCO3 and ... | FC(F)(F)c1cc(Cl)nc(-c2ccccc2Cl)c1 | null | null | null |
187,994 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | [BH4-].[Na+].C[O:4][C:5]([C@H:7]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH3:21])[C:9](=[O:22])[C@H:8]1[NH:23][C:24](=[O:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O>O1CCCC1>[CH3:21][O:20][C:13]1[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:12]=1[CH2:11][N:10... | COC(=O)[C@@H]1[C@H](NC(=O)Cc2ccccc2)C(=O)N1Cc1ccc(OC)cc1OC | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1.5 | Under ice-cooling and stirring, 12 ml of an aqueous solution containing 570 mg of sodium borohydride is added to a solution of 2.06 g of cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine-4-carboxylic acid methyl ester in 24 ml of tetrahydrofuran. The reaction mixture is stirred for 30 minutes under ice-cooli... | COc1ccc(CN2C(=O)[C@@H](NC(=O)Cc3ccccc3)[C@H]2CO)c(OC)c1 | null | 91.1 | null |
847,635 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [ClH:1].[CH:2]1([N:6]2[CH2:11][CH2:10][CH:9]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1>S(Cl)(Cl)=O>[ClH:1].[CH:2]1([N:6]2[CH2:11][CH2:10][CH:9]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([Cl:1])=[O:18])=[CH:15][CH:14]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2... | O=C(O)c1ccc(OC2CCN(C3CCC3)CC2)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | 4-[(1-Cyclobutyl-4-piperidinyl)oxy]benzoic acid hydrochloride (D24) (0.20 g) was dissolved in thionyl chloride (10 ml) and heated under reflux for 1.5 h. The thionyl chloride was removed by evaporation and the residue evaporated from DCM (3×10 ml) to give the title compound (D25) (0.21 g). | O=C(Cl)c1ccc(OC2CCN(C3CCC3)CC2)cc1 | null | 198.3 | null |
937,419 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:24][CH3:25])=[CH:13][C:14]=2[O:16][CH2:17][C@@H:18]2[NH:22][CH2:21][C@@H:20]([OH:23])[CH2:19]2)[N:9]=[CH:8][N:7]=1.[CH3:30][O:31][CH2:32][C:33](O)=[O:34]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[NH:5][C:6]... | COc1cc(OC[C@H]2C[C@H](O)CN2)c2c(Nc3ccc(F)c(Cl)c3)ncnc2c1 | COCC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The procedure described in Example 20 was repeated using (3S,5R)-5-[({4-[3-chloro-4-fluoroanilino]-7-methoxyquinazolin-5-yl}oxy)methyl]pyrrolidin-3-ol (120 mg) with methoxyacetic acid (24 μl) to give the title compound as a white solid in 60% yield; NMR spectrum (DMSO-d6) 9.96 (s, 1H), 8.45 (s, 1H), 8.17-8.14 (m, 1H), ... | COCC(=O)N1C[C@@H](O)C[C@@H]1COc1cc(OC)cc2ncnc(Nc3ccc(F)c(Cl)c3)c12 | null | 60 | null |
1,709,475 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[CH:9][N:8]([CH2:11][CH2:12]O)[C:7]=2[CH:14]=1.C(Br)(Br)(Br)[Br:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:16][CH2:12][CH2:11][N:8]1[C:7]2[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[N:10]=[CH:9]1 | BrC(Br)(Br)Br | COc1ccc2ncn(CCO)c2c1 | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 0 | 2 | To a solution of 2-(6-methoxy-1H-benzo[d]imidazol-1-yl)ethanol (200 mg, 1.04 mmol) in DCM (6.0 mL), CBr4 (397 mg, 1.20 mmol) was added, then the reaction mixture was cooled to 0° C. and PPh3 (314 mg, 1.20 mmol) was added. After stirring at rt for 2 h the solvent was removed under reduced pressure to yield the title com... | COc1ccc2ncn(CCBr)c2c1 | null | null | null |
128,765 | ord_dataset-d6b60b593b1c4668bc6843cd65a5d232 | null | 1985-01-01T00:04:00 | true | [NH2:1][C:2]1[C:3](=[O:16])[NH:4][C:5]2[CH2:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[CH:11]=1.N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)(Cl)Cl>[C:23]([NH:1][C:2]1[C:3](=[O:16])[NH:4][C:5]2[CH2:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[CH:11]=1)(=[O:25])[CH3:24] | Nc1cc2c([nH]c1=O)CCc1ccccc1-2 | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | To 2.0 gm of 2-amino-5,6-dihydrobenzo[f]quinolin-3(4H)-one, in 100 ml of chloroform containing 1 ml of pyridine add 0.80 gm of acetyl chloride. Stir the reaction at room temperature for 5 hours. Filter and wash the solution with water. Remove the solvent by stripping to give the title compound. | CC(=O)Nc1cc2c([nH]c1=O)CCc1ccccc1-2 | null | null | null |
804,404 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [NH2:1][CH:2]1[CH:7]([CH:8]=O)[CH:6]=[N:5][C:4]([S:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:3]1.[CH2:15]([O:17][CH2:18][C:19](OCC)=[O:20])[CH3:16].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH2:11]([S:10][C:4]1[N:5]=[CH:6][CH:7]2[CH:8]=[C:18]([O:17][CH2:15][CH3:16])[C:19](=[O:20])[NH:1][CH:2]2[N:3]=1)[CH2:12][CH2:13][CH3:14] | CCCCSC1=NC(N)C(C=O)C=N1 | CCOCC(=O)OCC | null | CC(C)(C)[O-] | [K+] | 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 | 48 | 4-Amino-2-butylsulfanyl-4,5-dihydro-pyrimidine-5-carbaldehyde (3 g, 14.2 mmol, funished by scaleup) and ethyl ethoxyacetate (2.34 g, 2.4 ml, 17.75 mmol) were stirred in 80 ml toluene at 0°-5° C. under nitrogen. Potassium t-butoxide (1.75 g, 15.6 mmol) was added gradually. The mixture was stirred to ambient temperature,... | CCCCSC1=NC2NC(=O)C(OCC)=CC2C=N1 | null | null | null |
488,170 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | C[O:2][C:3]1[N:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].B(Cl)(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[N:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6] | COc1ccc(C=O)c(OC)n1 | null | null | ClB(Cl)Cl | 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 | 20 | 8.4 g (0.05 mol) 2,6-dimethoxy-nicotinaldehyde was solved in 75 ml methylene chloride. At 0° C. (0.2 mol) BCl3 as 1 molar solution in methylene chloride 200 ml was added and stirred at room temperature for 20 h. The mixture was poured on ice/water, neutralized and extracted with CH2Cl2. Evaporation of the solvent affor... | COc1ccc(C=O)c(O)n1 | null | 74.4 | null |
882,744 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | Cl.[NH2:2][C:3]1[CH:33]=[CH:32][C:6]2[NH:7][C:8]([C:13]3[C:14](=[O:31])[C:15]([CH3:30])([CH2:24][CH2:25][C@@H:26]([CH3:29])[CH2:27][CH3:28])[C:16]4[C:21]([C:22]=3[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[S:34](Cl)([CH3:37])(=[O:36])=[O:35].N1C=CC=CC=1>CC(C)=O>[OH:23][C:22]1... | CC[C@H](C)CCC1(C)C(=O)C(C2=NS(=O)(=O)c3cc(N)ccc3N2)=C(O)c2ccccc21 | CS(=O)(=O)Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | A solution of Example 43F (0.119 g, 0.240 mmol), mesyl chloride (0.075 mL, 0.970 mmol), and pyridine (0.157 mL, 1.94 mmol) in acetone (3 mL) was stirred at 25° C. for 18 hours. The solution was partitioned between ethyl acetate and dilute citric acid and the layers were separated. The ethyl acetate layer was dried with... | CC[C@H](C)CCC1(C)C(=O)C(C2=NS(=O)(=O)c3cc(NS(C)(=O)=O)ccc3N2)=C(O)c2ccccc21 | null | null | null |
1,567,568 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]([CH2:4][CH2:5][CH2:6][N:7]([CH3:66])[C@H:8]([C:12]([NH:14][C@H:15]([C:19]([N:21]([C@@H:23]([C@@H:62]([CH3:65])[CH2:63][CH3:64])[C@H:24]([O:60][CH3:61])[CH2:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C@H:33]([O:58][CH3:59])[C@@H:34]([CH3:57])[C:35]([NH:37][C@@H:38]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH... | CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)CS(=O)(=O)Cc1ccccc1)OC)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)CCCC(=O)O)C(C)C | NNC(=O)CCCCCN1C(=O)C=CC1=O | 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 | 7.4 mg (7.9 mmol) of N-(3-carboxypropyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(2S)-1-(benzylsulphonyl)-3-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide and 6.2 mg (23.5 mmol) of 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)... | CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)CS(=O)(=O)Cc1ccccc1)OC)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)CCCC(=O)NNC(=O)CCCCCN1C(=O)C=CC1=O)C(C)C | null | null | null |
1,331,765 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=2[N:6]=1.C([Sn](CCCC)(CCCC)[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)CCC.C(OCC)(=O)C>O1CCOCC1.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=CC=2)(C2C=CC=CC=2)C... | O=[N+]([O-])c1ccc2oc(Cl)nc2c1 | CCCC[Sn](CCCC)(CCCC)c1cccs1 | 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 | CCOC(C)=O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 100 | null | A mixture of 2-chloro-5-nitrobenzo[d]oxazole (404 mg, 2.04 mmol), 2-(tributylstannyl)-thiophene (648 μL, 2.04 mmol) and tetrakis(triphenylphosphine)palladium (0) (40.8 mg) in dioxane (12.2 mL) was heated at 100° C. for 16 h under nitrogen. Ethyl acetate was added, the organic layer was washed with water, dried over anh... | O=[N+]([O-])c1ccc2oc(-c3cccs3)nc2c1 | null | 0.6 | null |
1,564,450 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([CH3:12])[C:5]2=[N:6][CH:7]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([N:17]3[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]3)=[CH:9][N:8]([CH3:12])[C:5]2=[N:6][CH:7]=... | Cn1cc(I)c2cc(Br)cnc21 | CN1CCNCC1 | null | [Cu]I | O=P([O-])([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | OCCO | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 5-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.445 mmol), 1-methylpiperazine (356.7 mg, 3.56 mmol), copper(I) iodide (84.8 mg, 0.445 mmol), K3PO4 (378 mg, 1.78 mmol), 1,2-ethanediol (138 mg, 2.225 mmol) in isopropyl alcohol (5 mL) in a sealed tubes was heated at 70° C. for 2 days. After cool... | CN1CCN(c2cn(C)c3ncc(Br)cc23)CC1 | null | null | null |
1,751,514 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Br[C:10]1[S:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:14]=1.[OH-].[Na+]>C(OCC)(=O)C.O1CCCC1>[F:3][C:4]([F:8])([F:7])[CH2:5][O:6][C:10]1[S:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:14]=1 | COC(=O)c1cnc(Br)s1 | OCC(F)(F)F | null | [H-] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | To a tetrahydrofuran solution (5.0 mL) of sodium hydride (465 mg, 11.6 mmol) and 2,2,2-trifluoroethanol (1.70 mL, 23.3 mmol), methyl 2-bromothiazole-5-carboxylate (517 mg, 2.33 mmol) was added and the resultant mixture was stirred at room temperature for 2 hours. After completion of the reaction, 1 M sodium hydroxide a... | COC(=O)c1cnc(OCC(F)(F)F)s1 | null | 79 | null |
750,813 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[OH:12][C:13]1[CH:14]=[C:15]([C@@H:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[O:12][... | O=[N+]([O-])c1ccc(Cl)cc1F | C[C@H](NC(=O)OC(C)(C)C)c1cccc(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 | O | null | null | null | null | null | null | null | null | null | 100 | 1 | A mixture of 4-chloro-2-fluoronitrobenzene (10.4 g, 59.2 mmols), tert-butyl(1S)-1-(3-hydroxyphenyl)ethylcarbamate (13.4 g, 56.5 mmols), potassium carbonate (9.4 g, 68 mmols) and N,N-dimethylformamide (150 ml) was stirred at 100° C. for 1 hour. The reaction mixture was cooled, poured into water, and extracted with ethyl... | C[C@H](NC(=O)OC(C)(C)C)c1cccc(Oc2cc(Cl)ccc2[N+](=O)[O-])c1 | null | 70.7 | null |
751,324 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[N+:12]([O-])=O)[CH:2]=[CH2:3].[NH4+].[Cl-].C(O)C>[Fe].O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[NH2:12])[CH:2]=[CH2:3] | C=CCOc1ccc(Br)cc1[N+](=O)[O-] | null | null | [Fe] | [Cl-] | [NH4+] | 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 | A mixture of Example 66A (5.06 g, 19.69 mmol), iron powder (11.02 g, 196.9 mmol), NH4Cl (0.53 g, 9.85 mmol), ethanol (160 mL), and water (40 mL) were heated at 80° C. for 6 hours. The solution was filtered, concentrated with silica gel powder (18 g), and purified by flash chromatography eluting with 10% ethyl acetate i... | C=CCOc1ccc(Br)cc1N | null | 100.9 | null |
1,388,111 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](SC)=[N:7][C:8]([C:12]([F:21])([F:20])[C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=3)=[N:9]2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=O.[CH3:35][C:36]1[NH:40][N:39]=[C:38]([NH2:41])[CH:37]=1>C(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:41][C:38]3[CH:37]=[C:36]([CH3:... | Cc1cc(N)n[nH]1 | CSc1nc(C(F)(F)c2ccc(F)cn2)nc2cc(Br)ccc12 | null | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 1.33 | To 7-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline (100 mg, 0.25 mmol) in DCM (3 mL) at 0° C. was added 70% meta-chloroperoxybenzoic acid (74 mg, 0.30 mmol) and the mixture was stirred at 0° C. for 80 min. Then additional 70% meta-chloroperoxybenzoic acid (70%, 15 mg, 0.086 mmol) was added an... | Cc1cc(Nc2nc(C(F)(F)c3ccc(F)cn3)nc3cc(Br)ccc23)n[nH]1 | null | 3.9 | null |
965,776 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | C(Cl)(Cl)Cl.[N+:5]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([F:16])[CH:9]=1)([O-:7])=[O:6].[CH2:17]([Si](C)(C)C)[CH:18]=[CH2:19]>C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl>[F:16][C:10]1[CH:9]=[C:8]([N+:5]([O-:7])=[O:6])[CH:15]=[CH:14][C:11]=1[CH:12]([OH:13])[CH2:19][CH:18]=[CH2:17] | C=CC[Si](C)(C)C | O=Cc1ccc([N+](=O)[O-])cc1F | null | Cl[Ti](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 0.17 | 0.65 ml of titanium tetrachloride was added to a chloroform (12 ml) solution of 2.00 g of 4-nitro-2-fluoro-benzaldehyde produced according to the method described in U.S. Pat. No. 6,239,152, and the reaction liquid was stirred at room temperature for 10 minutes, and then 2.4 ml of allyl-trimethyl-silane was added to it... | C=CCC(O)c1ccc([N+](=O)[O-])cc1F | null | null | null |
606,631 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH:28]3[O:30][CH2:29]3)=[C:22]([CH3:31])[CH:21]=2)[CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[CH2:32]([NH2:36])[CH2:33][CH2:34][CH3:35]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]... | COc1ccc(C(c2ccc(OCC3CO3)c(C)c2)C2CCCc3ccccc32)cc1 | CCCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of (4-methoxyphenyl)-(3-methyl-4-(2,3-epoxypropyloxy)phenyl)-1,2,3,4-tetrahydronaphth-1-yl-methane (300 mg, 0.001 mol), n-butyl amine (1.0 m, 0.01 mol) and ethanol (15 ml) was refluxed for 8 hrs. Ethanol was distilled off and the residue was passed through a basic alumina column using hexane:ethyl acetate as ... | CCCCNCC(O)COc1ccc(C(c2ccc(OC)cc2)C2CCCc3ccccc32)cc1C | null | null | null |
380,891 | ord_dataset-993feac5ecf54388aa6326a220e46db3 | null | 1997-01-01T00:10:00 | true | [CH:1]([C:3]1[CH:4]=[C:5]([S:14]([OH:17])(=[O:16])=[O:15])[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[C:12]=1[OH:13])=[O:2].C(=O)([O-])[O-:19].[Na+].[Na+].[K]>>[C:1]([C:3]1[CH:4]=[C:5]([S:14]([OH:17])(=[O:16])=[O:15])[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[C:12]=1[OH:13])([OH:19])=[O:2] | O=Cc1cc(S(=O)(=O)O)c2cccnc2c1O | O=C([O-])[O-] | null | [K] | [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 | 52 | 0.92 | The 7-formyl-8-hydroxyquinoline-5-sulfonic acid (15 mmol, 3.80 g) was dissolved in sodium carbonate solution (34.5 mmol, 3.66 g in 200 mL of H2O). The solution was stirred and heated at 52° C. (oil bath). Then to the hot solution potassium permaganate (37.5 mmol, 5.94 g) was added. The temperature was increased to 68° ... | O=C(O)c1cc(S(=O)(=O)O)c2cccnc2c1O | null | 48.5 | null |
418,927 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([NH:20][S:21]([C:24]1[CH:33]=[C:32]([NH:34][NH2:35])[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27])(=[O:23])=[O:22])([CH3:19])([CH3:18])[CH3:17].[C:36]1([CH2:42][C:43](O)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:16]([NH:20][S:21]([C:24]1[CH:33]=[C:3... | O=C(O)Cc1ccccc1 | COC(=O)c1ccc(NN)cc1S(=O)(=O)NC(C)(C)C | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccncc1 | 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 | 15 | 1.5 g (7.3 mmol) of dicyclohexylcarbodiimide (DCC) are added to a solution of 2.0 g (6.6 mmol) of methyl 2-(N-tert-butylsulfamoyl)-4-hydrazinobenzoate, 0.9 g (6.6 mmol) of phenylacetic acid and 0.03 g of 4-dimethylaminopyridine (DMAP) in 20 ml of CH2Cl2 at 0° C. The mixture is stirred at 25° C. for 15 hours, the solid ... | COC(=O)c1ccc(NNC(=O)Cc2ccccc2)cc1S(=O)(=O)NC(C)(C)C | null | null | null |
178,376 | ord_dataset-4d84abdf99524e0fb6c42ab2a3300790 | null | 1988-01-01T00:10:00 | true | C[Li].[N+:3]([C:6]1[CH:49]=[CH:48][CH:47]=[CH:46][C:7]=1[CH2:8][O:9][C:10]([CH:12]([PH:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[N:13]1[CH:16]([CH2:17][C:18]([C:20]2C=CC=CC=2)=S)[CH2:15][C:14]1=[O:26])=[O:11])([O-:5... | CCOCC | O=C(OCc1ccccc1[N+](=O)[O-])C(N1C(=O)CC1CC(=S)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1 | null | [Cl-] | [Li]C | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.08 | Cuprous iodide (0.380 g) is suspended in 10 ml anhydrous ether under N2, in a dry flask and cooled to 0°. Methyl lithium (3.0 ml, 1.3 Molar) is added dropwise and the mixture is stirred at 0° for 5 min to give a yellow suspension. The mixture is then cooled to -50°. 1-(o-nitrobenzyloxycarbonyl-triphenylphosphoranylmeth... | CC(=O)CC1CC(=O)N1C(C(=O)OCc1ccccc1[N+](=O)[O-])[PH](c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null |
220,755 | ord_dataset-42629b4cf1094978a5e5f29f22639ee7 | null | 1991-01-01T00:01:00 | true | [CH3:1][O-:2].[Na+].[SH:4][CH2:5][CH2:6][CH2:7][Si:8]([O:13][CH3:14])([O:11][CH3:12])[O:9][CH3:10].II>CO>[CH3:12][O:11][Si:8]([O:13][CH3:14])([O:9][CH3:10])[CH2:7][CH2:6][CH2:5][S:4][S:4][CH2:5][CH2:6][CH2:7][Si:8]([O:11][CH3:12])([O:9][CH3:10])[O:2][CH3:1] | C[O-] | CO[Si](CCCS)(OC)OC | null | II | [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 28% solution of sodium methylate in methanol (97.6 g. 0.51 mole) is diluted with methanol (100 ml), and thereto is added γ-mercaptopropyltrimethoxysilane (100 g, 0.51 mole). The temperature of the mixture raises in a certain degree owing to the mixing heat but return to room temperature after about 30 minutes. To the... | CO[Si](CCCSSCCC[Si](OC)(OC)OC)(OC)OC | null | null | null |
1,588,262 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[Br:10]N1C(=O)CCC1=O>ClC1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:10][CH2:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=1 | Cc1cnc(Cl)cc1Cl | O=C1CCC(=O)N1Br | null | CC(C)(C#N)N=NC(C)(C)C#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 132 | 16 | 2,4-dichloro-5-methylpyridine (13.64 g, 82.50 mmol), N-bromosuccinimide (15.42 g, 86.63 mmol) were dissolved in chlorobenzene (300 mL). 2,2′-azobis(isobutyronitrile) (1.355 g, 8.250 mmol) in chlorobenzene (160 mL) was added slowly in two times: first approximately a third of the total amount at room temperature, then t... | Clc1cc(Cl)c(CBr)cn1 | null | 125.3 | null |
1,435,245 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [C:1]([C:5]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:6]=1[C:7]([O-:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH:17]([O-])=O.[K+]>CCO.O.[Pd]>[C:1]([C:5]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:6]=1[C:7]([O:9][CH3:17])=[O:8])([CH3:4])([CH3:3])[CH3:2] | O=C[O-] | CC(C)(C)c1ccc([N+](=O)[O-])cc1C(=O)[O-] | null | [Pd] | [K+] | 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 | To a refluxing solution of 2-tert-butyl-5-nitrobenzoate (90 mg, 0.38 mmol) in EtOH (2.0 mL) was added potassium formate (400 mg, 4.76 mmol) in water (1 mL), followed by the addition of 20 mg of 10% Pd—C. The reaction mixture was refluxed for additional 40 min, cooled to room temperature and filtered through Celite. The... | COC(=O)c1cc(N)ccc1C(C)(C)C | null | 96.5 | null |
1,610,872 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | Cl[C:2]1[C:7]([F:8])=[C:6]([CH:9]=[N:10]O)[CH:5]=[CH:4][N:3]=1>C(O)(=O)C.[Zn]>[F:8][C:7]1[CH:2]=[N:3][CH:4]=[CH:5][C:6]=1[CH2:9][NH2:10] | ON=Cc1ccnc(Cl)c1F | null | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 2 | Zinc dust (2.52 g, 38.6 mmol) was added at RT to a solution of 2-chloro-3-fluoro-pyridine-4-carbaldehyde oxime (1.34 g, 6.29 mmol) in acetic acid (30 mL). The reaction mixture was stirred at RT for 2 h, then concentrated in vacuo. The colored oily residue was partitioned between CH2Cl2 and 1N HCl. The layers were separ... | NCc1ccncc1F | null | null | null |
1,166,627 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([Cl:12])=[N:6][CH:5]=1.[OH-].[Na+].Cl>CO>[Cl:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:4]([C:3]([OH:13])=[O:2])=[CH:5][N:6]=1 | COC(=O)c1cnc(Cl)c(OC)c1 | 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 | null | 24 | To a solution of 6-chloro-5-methoxynicotinic acid methyl ester (1.3 g, 6.4 mmol) in MeOH (4 mL) at 25° C. was added 10% NaOH aqueous solution (19.3 mmol). The reaction was stirred for 24 h, then placed into an ice water bath and acidified with 2M HCl until pH=2 was achieved. The flask was then placed into a refrigerato... | COc1cc(C(=O)O)cnc1Cl | null | 74.6 | null |
913,228 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][C:10]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][C:18]=2[CH3:27])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:35][C:36]([O:38]C(C)(C)C)=[O:37]>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:8]1[C:13](=[O:14])[... | CC(C)(C)OC(=O)CBr | Cc1[nH]c2ccc(Cl)cc2c1C1=NN(Cc2ccccc2)C(=O)C(C)(C)C1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 80 | null | The product of step b) (˜0.3 mmol) was dissolved in 5 mL DMF and treated with K2CO3 (1 mmol, 138 mg) and t-butyl bromoacetate (1 mmol, 195 mg). After heating to 80° C. for ½ h, the reaction was cooled, diluted with EtOAc and washed 5× water. The reaction was concentrated, dissolved in EtOH (5 mL) and treated with 1.4 m... | Cc1c(C2=NN(Cc3ccccc3)C(=O)C(C)(C)C2)c2cc(Cl)ccc2n1CC(=O)O | null | null | null |
396,197 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [C:1](Cl)(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1>ClCCl.N1C=CC=CC=1>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([NH:21][C:1](=[O:19])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][S... | O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | N#Cc1ccc(N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 4-aminobenzonitrile (1.38 g, 11.7 mmol) in 11 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate and ethanol (1:1), filtered... | N#Cc1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(C#N)cc2)cc1 | null | 12.5 | null |
367,615 | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | null | 1997-01-01T00:06:00 | true | [C:1]1([P:7](=[O:17])([O-:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[C:1]1([P:7](=[O:16])([O:17][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24]... | O=P([O-])(OCc1ccccc1)c1ccccc1 | ClCCN1CCOCC1 | 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 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 65 | 22 | A mixture of monobenzyl phenylphosphonate (115 mg, 0.46 mmol), N-(2-chloroethyl)morpholine hydrochloride (95 mg, 0.51 mmol) and potassium carbonate (140 mg, 1.0 mmol) in anhydrous DMF was stirred at 65° C. for 22 hours. Following dilution with ethyl acetate (40 ml), the mixture was washed with water four times and fina... | O=P(OCCN1CCOCC1)(OCc1ccccc1)c1ccccc1 | null | 74.6 | null |
1,719,767 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH:13]([OH:15])[CH3:14].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.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)(C... | OB(O)c1ccccc1 | CC(O)c1oc(=O)c2ccccc2c1Br | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 120 | null | 4-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 0.77 g, 2.88 mmol), phenylboronic acid (0.63 g, 5.18 mmol), Pd(PPh3)4 (0.199 g, 0.173 mmol) and Cs2CO3 (1.49 g, 4.6 mmol) were dissolved in DMF (10.7 ml) and heated under microwave irradiation at 120° C. for 20 min. The reaction mixture was then diluted w... | CC(O)c1oc(=O)c2ccccc2c1-c1ccccc1 | null | null | null |
169,464 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | Cl.[CH2:2]([O:4][C:5]([C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=[N:9][CH:8]=1)=[O:6])[CH3:3].[CH2:20](O)CC>>[CH2:2]([O:4][C:5]([C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=[N:9][CH:8]=1)=[O:6])[CH2:3][CH3:20] | CCCO | CCOC(=O)c1cncc2[nH]c3ccccc3c12 | 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 compound is produced by transesterification of the β-carboline-4-carboxylic acid-ethyl ester-hydrochloride with n-propanol. | CCCOC(=O)c1cncc2[nH]c3ccccc3c12 | null | null | null |
462,064 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | O[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:4][C:3]=1OC.[F:32]C1C=CC(C=CCBr)=CC=1>>[F:32][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:16][CH2:15][... | Fc1ccc(C=CCBr)cc1 | COc1cc(/C=C/CN2CCC(c3ccc(Oc4ccccc4)cc3)CC2)ccc1O | null | null | null | null | null | null | null | 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 same procedure was followed as in Example 11 using the compound (9) synthesized in Example 2 and 4-fluorocinnamyl bromide to produce the above. | Fc1ccc(/C=C/CN2CCC(c3ccc(Oc4ccccc4)cc3)CC2)cc1 | null | null | null |
1,275,190 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [H-].[Na+].[Br:3][C:4]1[C:5](Cl)=[N:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1.[CH2:14]([OH:19])[C:15]([F:18])([F:17])[F:16]>>[Br:3][C:4]1[C:5]([O:19][CH2:14][C:15]([F:18])([F:17])[F:16])=[N:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1 | OCC(F)(F)F | O=[N+]([O-])c1cnc(Cl)c(Br)c1 | 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 | 25 | 0.5 | Sodium hydride (3.2 g, 80.02 mmol) was added carefully in small portions to 2,2,2-trifluroethanol (CAS Registry No. 75-89-8) (60 ml) at 0° C. under nitrogen atmosphere and stirred at 25° C. for 30 minutes. Then 3-bromo-2-chloro-5-nitropyridine (CAS Registry No. 5470-17-7) (2 g, 8.42 mmol) in trifluoroethanol was added,... | O=[N+]([O-])c1cnc(OCC(F)(F)F)c(Br)c1 | null | 95 | null |
1,083,085 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [F:1][C:2]1[CH:3]=[C:4]([NH2:31])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[O:19][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)=[CH:21][CH:22]=3)[S:17][C:10]=12.C1(C)C=CC=CC=1.C(O)C.[C:42]1([CH2:48][C:49]([N:51]=[C:52]=[S:53])=[O:50])[CH:47]=[CH:46][CH:4... | CN1CCN(Cc2ccc(-c3cc4nccc(Oc5ccc(N)cc5F)c4s3)o2)CC1 | O=C(Cc1ccccc1)N=C=S | null | null | null | null | 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 | 25 | 0.5 | To a 5 mL round bottom flask was added 3-fluoro-4-(2-(5-((4-methylpiperazin-1-yl)methyl)furan-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine (32 mg, 0.0713 mmol) and 1:1 toluene/ethanol (1 mL). 2-Phenylethanoyl isothiocyanate (25.3 mg, 0.143 mmol; prepared according to the procedure described by J. Org. Chem. 1964, 29, ... | CN1CCN(Cc2ccc(-c3cc4nccc(Oc5ccc(NC(=S)NC(=O)Cc6ccccc6)cc5F)c4s3)o2)CC1 | null | 10 | null |
1,570,647 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21... | O=Cc1cccnc1 | O=S(=O)(c1cccc(C(F)(F)F)c1)N(C1CCNCC1)C1CC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 12 | To a solution of N-cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzenesulfonamide (150 mg, 0.43 mmol) and pyridine-3-carboxaldehyde (46 mg, 0.43 mmol) in dichloroethane was added sodium triacetoxyborohydride (128 mg, 0.60 mmol, 1.4 eq.). The reaction mixture was stirred at room temperature for 12 hours. After this p... | O=S(=O)(c1cccc(C(F)(F)F)c1)N(C1CC1)C1CCN(Cc2cccnc2)CC1 | null | null | null |
911,768 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][Cl:20])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CO.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][Cl:20])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1 | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCl | null | null | O=S([O-])S(=O)[O-] | [Na+] | 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 | 0 | 2 | A suspension of (7-bromo-3-nitroquinolin-4-yl)-(4-chlorobutyl)amine (8.05 g, 22.5 mmol) in methanol (250 mL) was cooled to 0° C.; a solution of sodium hydrosulfite (19.5 g, 112 mmol) in water (80 mL) was added dropwise over a period of 30 minutes. The reaction was stirred at ambient temperature for two hours and then c... | Nc1cnc2cc(Br)ccc2c1NCCCCCl | null | 98 | null |
584,370 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([Cl:15])[CH:9]=1)=[O:6].[Cl:21][C:22]1[CH:23]=[C:24]([N:29]=[C:30]=[S:31])[CH:25]=[C:26]([Cl:28])[CH:27]=1>ClCCl.CN(C=O)C>[Cl:15][C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:16]=[CH:17][C:18]([O:... | COc1ccc(C(=O)Nc2ccc(C)c(Cl)c2)cc1N | S=C=Nc1cc(Cl)cc(Cl)c1 | null | null | null | 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 | null | 16 | A solution of 3-amino-N-(3-chloro-4-methylphenyl)-4-methoxy-benzamide from Example 12 (0.581 g, 2.00 mmol) and 3,5-dichlorophenyl isothiocyanate (0.409 g, 2.00 mmol) in dichloromethane (40 mL) and DMF (3 mL) was allowed to stand at room temperature. After 16 hours, filtration afforded the product (0.57 g); m.p. 195-196... | COc1ccc(C(=O)Nc2ccc(C)c(Cl)c2)cc1NC(=S)Nc1cc(Cl)cc(Cl)c1 | null | 57.6 | null |
476,334 | ord_dataset-d56f0a7ec215495c92e641d9fa932d28 | null | 2000-01-01T00:09:00 | true | [F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.C(OP([CH2:21][C:22](=[O:27])[NH:23][CH:24]1[CH2:26][CH2:25]1)(=O)OCC)C>>[CH:24]1([NH:23][C:22](=[O:27])/[CH:21]=[C:9]2\[CH2:8][CH2:7][CH2:6][C:5]3[C:10]\2=[CH:11][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:26][CH2:25]1 | O=C1CCCc2ccc(F)cc21 | CCOP(=O)(CC(=O)NC1CC1)OCC | null | null | null | null | null | null | null | 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 in an analogous manner to Example 12f with the replacement of 5-fluoro 1-tetralone and diethyl (cyclopropylcarbamoyl)methyl phosphonate with 7-fluoro-1-tetralone (7.76 g, 0.05 mol) and diethyl(cyclopropylcarbamoyl)methylphosphonate (11.1 g, 0.05 mol). Chromatography on Silca gel using ethyl a... | O=C(/C=C1\CCCc2ccc(F)cc21)NC1CC1 | null | null | null |
409,658 | ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2 | null | 1998-01-01T00:08:00 | true | [F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)([OH:16])[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[CH:29]1([CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([CH2:40]Cl)=[CH:36][CH:35]=2)[CH2:31][CH2:30]1.CCN(C(C)C)C(C)... | ClCc1ccc(OCC2CC2)cc1 | OC(c1ccc(C(F)(F)F)cc1)(c1ccc(C(F)(F)F)cc1)C1CCNCC1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | A solution of 20.5 grams (0.051 mole) of 4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine, 10.0 grams (0.051 mole) of 4-(cyclopropylmeth-oxy)phenylmethyl chloride (prepared as in Step A of Example 1), and 35.4 mL (0.203 mole) of N,N'-diisopropylethylamine in 200 mL of dimethyl sulfoxide was stirred at ambient te... | OC(c1ccc(C(F)(F)F)cc1)(c1ccc(C(F)(F)F)cc1)C1CCN(Cc2ccc(OCC3CC3)cc2)CC1 | null | 76.5 | null |
1,017,316 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9](Br)[CH:10]=[CH2:11].C(=O)(O)[O-].[Na+]>CS(C)=O.[I-].[Na+]>[C:2]1([CH2:1][NH:8][CH2:11][CH:10]=[CH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | NCc1ccccc1 | C=CCBr | null | O=C([O-])O | [I-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of benzylamine (5.7 ml, 52.2 mmol) and sodium iodide (38 mg, 0.25 mmol) in DMSO (30 ml) was added dropwise allyl bromide (2.2 ml, 25.4 mmol) at 0° C. under argon. After stirring for 3 h at room temperature the reaction was complete as shown by TLC (cyclohexanes:ethyl acetate 1:1). Then saturated aqueous s... | C=CCNCc1ccccc1 | null | 56.2 | null |
1,240,011 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[NH2:13][C:14]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1>>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:18]2[... | Nc1cc(COc2ccc(Br)cc2)ccc1Sc1ccc(O)cc1 | Cc1ccc2c(Cl)ccnc2n1 | null | null | null | null | null | 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 | The product from Example 1d (0.03 g, 0.167 mmol) was reacted with the product from Example 223c (0.060 g, 0.15 mmol) for 17.5 h following the procedure from Example 1g. Consumption of starting material required a second addition of the product from Example 1d (0.016 g, 0.09 mmol) and continued heating at 80° C. (18 h).... | Cc1ccc2c(Nc3cc(COc4ccc(Br)cc4)ccc3Sc3ccc(O)cc3)ccnc2n1 | null | null | null |
37,525 | ord_dataset-b0ddd49dad024fc7a23ae6f474f9c52f | null | 1978-01-01T00:03:00 | true | Cl[C:2]1[C:3]2[N:4]([N:13]=[CH:14][C:15]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]2[N:10]([CH3:11])[N:9]=[C:8]([CH3:12])[C:6]=2[N:7]=1.[SH-:21].[Na+]>C(O)CC>[CH3:11][N:10]1[C:5]2[N:4]3[N:13]=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:3]3[C:2]([SH:21])=[N:7][C:6]=2[C:8]([CH3:12])=[N:9]1 | CCOC(=O)c1cnn2c1c(Cl)nc1c(C)nn(C)c12 | [SH-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCO | null | null | null | null | null | null | null | null | null | null | null | null | 5.86 gms. of 5-chloro-1,3-dimethyl-1H-dipyrazolo[1,5-a:4',3'-e]pyrazine-6-carboxylic acid, ethyl ester, are refluxed with 2 gms. of sodium bisulfide and 50 ml. of n-propanol for 3 hours. On cooling, the product, 1,3-dimethyl-5-mercapto-1H-dipyrazolo[1,5-a:4',3'-e]pyrazine-6-carboxylic acid, ethyl ester, crystallizes in... | CCOC(=O)c1cnn2c1c(S)nc1c(C)nn(C)c12 | null | null | null |
1,564,805 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | C[O:2][C:3](=[O:53])[C@@H:4]([NH:20][C:21]([C@@H:23]1[CH2:32][C:31]2[CH:30]=[C:29]3[O:33][CH2:34][C@H:35]([C:37]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=5)=[CH:39][CH:38]=4)[O:36][C:28]3=[CH:27][C:26]=2[CH2:25][NH:24]1)=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C... | CCC(C)(C)N=C=O | COC(=O)[C@H](Cc1ccc(-c2ccnc(C)c2C)cc1)NC(=O)[C@@H]1Cc2cc3c(cc2CN1)O[C@@H](c1ccc(OCc2ccc(Cl)c(Cl)c2)cc1)CO3 | null | [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 | (S)-2-({(3S,8S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester (20 mg) was reacted with 2-isocyanato-2-methyl-butane (prepared according to General Procedure AD) according to General Proc... | CCC(C)(C)NC(=O)N1Cc2cc3c(cc2C[C@H]1C(=O)N[C@@H](Cc1ccc(-c2ccnc(C)c2C)cc1)C(=O)O)OC[C@H](c1ccc(OCc2ccc(Cl)c(Cl)c2)cc1)O3 | null | null | null |
139,376 | ord_dataset-7d359d96b3a64882921ebdc6c850e22e | null | 1986-01-01T00:01:00 | true | C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:27][O:28][CH2:29][C:30]#[CH:31])[C:10]([NH:12][CH:13]2[C:25](=[O:26])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[C:17]([O:20][CH3:21])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:27][O:28][CH2:29][C:30]#[CH:31])[C:10]([NH:12][CH:13]2[C:2... | C#CCON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(OC)CS[C@H]12)c1csc(NC=O)n1 | 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 | 4 | A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn isomer, 0.9 g.), conc. hydrochloric acid (0.9 ml.) and methanol (13.5 ml.) was stirred at room temperature for 4 hours. After concentrating the resultant solution in vacuo at 35° C., the residue was disso... | C#CCON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(OC)CS[C@H]12)c1csc(N)n1 | null | 29.6 | null |
898,778 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH:14]2[CH2:16][CH2:15]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].C1COCC1>CO>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH:14]2[CH2:16][CH2:15]2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5] | COC(=O)c1ccc(C#CC2CC2)cc1Cl | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 5 | A mixture of methyl 2-chloro-4-(2-cyclopropylethynyl)benzoate (310 mg, 0.0013 mol), 2N aq. NaOH (3.0 mL), THF (5 mL), and MeOH (5 mL) was stirred at rt for 5 h. The mixture was concentrated under vacuum and the residue was treated with water and acidified with 1N HCl to pH 2-3, and extracted with EtOAc. The organic lay... | O=C(O)c1ccc(C#CC2CC2)cc1Cl | null | 94.1 | null |
82,813 | ord_dataset-b1023e5ccd7142de9d250aa2e3e124db | null | 1981-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=3[C:12]=2[N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1.[C:23](Cl)(=[O:32])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(N(CC)CC)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:22]=... | Clc1ccc(-c2oc3ccccc3c2N2CCNCC2)cc1 | CCCCCCCCC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 0.5 | To the solution of 56 g of 1-(2-p-chlorophenyl-3-benzofuryl)piperazine in 25.2 g of triethylamine and 500 ml of methylene chloride, 31.7 g of pelargonic acid chloride in 300 ml of methylene chloride are added while stirring at 0° for 1/2 hour and stirring is continued for 15 hours. The mixture is washed successively wi... | CCCCCCCCC(=O)N1CCN(c2c(-c3ccc(Cl)cc3)oc3ccccc23)CC1 | null | null | null |
577,320 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | [O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[C:7]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:6][CH:5]=[CH:4][C:3]1=2.[H-].[Na+].[CH3:19][O:20][CH2:21]Cl.O>CN(C=O)C>[CH3:19][O:20][CH2:21][N:12]([C:7]1[C:8]2[CH2:9][CH2:10][CH2:11][C:2](=[O:1])[C:3]=2[CH:4]=[CH:5][CH:6]=1)[S:13]([CH3:16])(=[O:15])=[O:14] | COCCl | CS(=O)(=O)Nc1cccc2c1CCCC2=O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 0.75 | A solution of Example 15A (4.0 g, 17 mmol) in anhydrous DMF (40 mL) under a nitrogen atmosphere was treated with a 60% dispersion of sodium hydride (0.74 g, 18 mmol) in portions over 5 minutes, stirred for 45 minutes, cooled to 0° C., treated dropwise with chloromethyl methyl ether (1.3 mL, 18 mmol), stirred at ambient... | COCN(c1cccc2c1CCCC2=O)S(C)(=O)=O | null | null | null |
122,637 | ord_dataset-a9b95e50436441ff8f3f12dd60d1e1b2 | null | 1984-01-01T00:10:00 | true | [NH:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)C(C)=O.[OH-].[Na+]>Cl>[NH2:1][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])=[CH:9][CH:10]=1 | CCCC(=O)c1ccc(NC(C)=O)cc1 | 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 | 0 | null | 20 g of p-acetaminobutyrophenone are suspended in 40 ml of semi-concentrated hydrochloric acid and the suspension is heated under reflux for 25 minutes and poured into a mixture of 100 ml of ice and 30 ml of concentrated sodium hydroxide solution. The mixture is filtered with suction, then the residue is washed twice w... | CCCC(=O)c1ccc(N)cc1 | null | null | null |
1,509,290 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [CH2:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([S:22]([N:25](CC3C=CC(OC)=CC=3OC)[C:26]3[CH:31]=[CH:30][N:29]=[CH:28][N:27]=3)(=[O:24])=[O:23])=[C:17]([F:43])[CH:16]=2)[C@@H:11]([C:44]2[N:48]([CH3:49])[N:47]=[CH:46][CH:45]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)... | COc1ccc(CN(c2ccncn2)S(=O)(=O)c2cc(F)c(O[C@H]3C[C@@H](OCc4ccccc4)C[C@@H]3c3ccnn3C)cc2F)c(OC)c1 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | The reaction and aftertreatment were conducted in the same manner as in Example 1b by using the 4-{[(1S*,2R*,4S*)-4-(benzyloxy)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide (143 mg, 0.207 mmol) prepared in Example 98b, triethylsilane (0.20 mL), t... | Cn1nccc1[C@H]1C[C@H](OCc2ccccc2)C[C@@H]1Oc1cc(F)c(S(=O)(=O)Nc2ccncn2)cc1F | null | 81.2 | null |
1,740,336 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([NH:8][C:9](=[S:29])[NH:10][C:11]2[S:21][C:14]3[CH2:15][O:16][C:17]([CH3:20])([CH3:19])[CH2:18][C:13]=3[C:12]=2[C:22]([O:24]C(C)(C)C)=[O:23])=[O:7])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9](=[S:29])[NH:10][C:11]2[S:21][C:14]3[CH2:15][O... | CC(C)(C)OC(=O)c1c(NC(=S)NC(=O)c2ccc(F)cc2)sc2c1CC(C)(C)OC2 | 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 | 25 | 1 | A solution of 40% v/v TFA/DCM (20 mL) was added to tert-butyl 2-(3-(4-fluorobenzoyl)thioureido)-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.33 g, 0.71 mmol) and the mixture was stirred at RT for 1 hour. The volatiles were removed at 30° C. and the material was purified by reverse-phase chromatograph... | CC1(C)Cc2c(sc(NC(=S)NC(=O)c3ccc(F)cc3)c2C(=O)O)CO1 | null | 71.8 | null |
6,520 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | [CH3:1][S:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)=[O:3].[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1>FC(F)(F)S(O)(=O)=O>[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[C:18]([CH:19]=1)[C:8]([C:7]1[CH:11]=[CH:12][C:4]([S:2]([CH3:1])=[O:3])=[CH:5][CH:6]=1)=[O:9] | Cc1ccc(F)cc1 | CS(=O)c1ccc(C(=O)Cl)cc1 | null | O=S(=O)(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | p-Methylsulfinylbenzoyl chloride (0.2 mole) and p-fluorotoluene (0.2 mole) are refluxed together in trifluoromethanesulfonic acid for 6 hours according to the procedure of Chodroff and Klein, J.A.C.S. 70, 7209 (1948). | Cc1ccc(F)cc1C(=O)c1ccc(S(C)=O)cc1 | null | null | null |
695,599 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [CH:1]([C:4]1[C:5](=[O:21])[NH:6][C:7](=[O:20])[NH:8][C:9]=1[C:10](=[O:19])[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=1)([CH3:3])[CH3:2].Cl[CH2:23][C:24]1[C:25]2[C:30]([CH:31]=[C:32]3[C:37]=1[CH:36]=[CH:35][CH:34]=[CH:33]3)=[CH:29][CH:28]=[CH:27][CH:26]=2>>[CH:26]1[C:25]2[C:30](=[CH:31][C:32]3[C:37]... | ClCc1c2ccccc2cc2ccccc12 | Cc1cc(C)cc(C(=O)c2[nH]c(=O)[nH]c(=O)c2C(C)C)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 | 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound (192 mg, yield: 40.3%). | Cc1cc(C)cc(C(=O)c2c(C(C)C)c(=O)[nH]c(=O)n2Cc2c3ccccc3cc3ccccc23)c1 | null | 40.3 | null |
578,478 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl[C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][N:27]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:17]2[CH:18]=[C:19]([CH:25]=[CH:26][N:27]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:6]=[C:7]([O:11][CH3:12])[C:8... | COc1cc(B(O)O)cc(OC)c1OC | CCOC(=O)c1ccnc(Cl)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 | 3,4,5-Trimethoxyphenylboronic acid (15.29 g) and ethyl 2-chloroisonicotinate (13.39 g) were reacted in the same manner as in Preparation Example 1 to obtain the title compound. | CCOC(=O)c1ccnc(-c2cc(OC)c(OC)c(OC)c2)c1 | null | null | null |
1,641,909 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [OH:1][C:2]([CH3:29])([CH3:28])[CH:3]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[O:4][C:5]1[C:6]([NH:15][S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.ClC1C=CC=C(C(OO)=[O:38])C=1>ClCCl>[OH:1][C:2]([CH3:28])([CH3:29])[CH:3]([C:22]1[CH:23]=[N+:24]([O-:38])... | O=C(OO)c1cccc(Cl)c1 | CCCS(=O)(=O)Nc1nc2ccccc2nc1OC(c1cccnc1)C(C)(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 | 25 | 2 | Compound 1 (89.6 mg, 0.215 mmol) obtained in Example 1 was dissolved in dichloromethane (5.0 mL). To the solution was added 65% meta-chloroperbenzoic acid (85.7 mg, 0.323 mmol) and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure. The residue was purified by pre... | CCCS(=O)(=O)Nc1nc2ccccc2nc1OC(c1ccc[n+]([O-])c1)C(C)(C)O | null | 51.3 | null |
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