original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,460,276 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[N:5][CH:4]=[N:3]1.[CH2:11]([C@H:18]1[CH2:22][NH:21][C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[N:2]1([CH2:7][C:8]([N:21]2[CH... | O=C(Nc1ccc(Oc2ccc(Cl)cc2)cc1)[C@@H]1C[C@@H](Cc2ccccc2)CN1 | O=C(O)Cn1cncn1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-chlorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 79, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-chlorophenoxy)phenyl)pyrrolidine-2-carboxamide (187 mg, 37%). 1H-NMR... | O=C(Nc1ccc(Oc2ccc(Cl)cc2)cc1)[C@@H]1C[C@@H](Cc2ccccc2)CN1C(=O)Cn1cncn1 | null | 37 | null |
352,623 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[NH:4][C:3]1=[O:12].[CH3:20][O:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[S:31](Cl)(=[O:33])=[O:32]>>[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:10... | NC1(c2ccccc2Cl)C(=O)Nc2ccc(Cl)cc21 | COc1cc([N+](=O)[O-])ccc1S(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound is prepared according to the procedure described in EXAMPLE 1 from 7 g of 3-amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one and 6 g of 2-methoxy-4-nitrobenzenesulfonyl chloride. The expected product is obtained after crystallization from a DCM/iso ether/THF mixture. m=9.4 g. M.p.=229° C. | COc1cc([N+](=O)[O-])ccc1S(=O)(=O)N1C(=O)C(N)(c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | null |
906,519 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]([F:24])([C:20]([F:23])([F:22])[F:21])[CH2:18]O>>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][CH2:18][C:17]([F:24])([F:16])[C:20]([F:23])([F:22])[F:21])(=[O:8])=[O:9] | OCC(F)(F)C(F)(F)F | O=S(=O)(OS(=O)(=O)C(F)(F)F)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 | 90 | null | A mixture of trifluoromethanesulfonic anhydride (40 mL, 0.24 mol) and 2,2,3,3,3-pentafluoropropanol (25 mL, 0.24 mol) was heated under argon at 90° C. overnight. Then, the crude mixture was distilled at atmospheric pressure to give the desired product as a colourless oil (97% yield). | O=S(=O)(OCC(F)(F)C(F)(F)F)C(F)(F)F | null | 97 | null |
653,931 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [CH2:1]([NH:4][C:5]([C:7]1([CH2:20][CH2:21][CH2:22][CH2:23]Br)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6])[CH2:2][CH3:3].[N:25]1([C:32]2[S:33][C:34]3[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=3[N:36]=2)[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[CH2:1]([NH:4][C:5]([... | CCCNC(=O)C1(CCCCBr)c2ccccc2-c2ccccc21 | c1ccc2sc(N3CCCNCC3)nc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 1 from 9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid-propylamide and 2-[1.4]diazepan-1-yl-benzothiazole. | CCCNC(=O)C1(CCCCN2CCCN(c3nc4ccccc4s3)CC2)c2ccccc2-c2ccccc21 | null | null | null |
1,719,797 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Si:1]([O:8][CH:9]([C:11]1[O:12][C:13](=[O:23])[C:14]2[C:19]([C:20]=1[CH:21]=O)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl.[O-]S([O-])(=O)=O.[Na+].[Na+]>[Si:1]([O:8][CH:9... | C1COCCN1 | CC(O[Si](C)(C)C(C)(C)C)c1oc(=O)c2ccccc2c1C=O | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=S(=O)([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a solution of 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1-oxo-1H-isochromene-4-carbaldehyde (Intermediate B59.2, 0.5 g, 1.5 mmol) and morpholine (0.12 ml, 1.35 mmol) in DCM (20 ml), dry Na2SO4 was added and the mixture stirred RT for 10 min. Sodium triacetoxyborohydride (0.286 g, 2.25 mmol) and acetic acid (0.09 ml,... | CC(O[Si](C)(C)C(C)(C)C)c1oc(=O)c2ccccc2c1CN1CCOCC1 | null | 33.3 | null |
667,033 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | [CH:1]1([C:6]([OH:19])([C:17]#[CH:18])[CH2:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[O:11][C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:21]1[S:22][CH:23]=[CH:24][N:25]=1.C(NC(C)C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH:1]1([C:6]([OH:19])... | C#CC(O)(CC1=CC(=O)OC(C)(C)O1)C1CCCC1 | Brc1nccs1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)NC(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | To a degassed solution of 6-(2-cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one (264.1 mg, 1.0; prepared as described in Example 1, Step 2), 2-bromothiazole (99.1 μL, 1.1 mmol), diisopropylamine (1.5 mL), and DMF (0.5 mL), under argon, was added Pd(PPh3)2Cl2 (28.1 mg, 0.04 mmol) and Cul (15.2 mg, 0.08 m... | CC1(C)OC(=O)C=C(CC(O)(C#Cc2nccs2)C2CCCC2)O1 | null | 81 | null |
526,351 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | [OH:1][CH:2]([CH2:5][CH2:6][S:7][CH3:8])[C:3]#[N:4].S(=O)(=O)(O)[OH:10]>>[OH:1][CH:2]([CH2:5][CH2:6][S:7][CH3:8])[C:3]([NH2:4])=[O:10] | CSCCC(O)C#N | O=S(=O)(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 | A process as set forth in claim 1 wherein 2-hydroxy-4-methylthiobutanenitrile is hydrolyzed in the presence of sulfuric acid to produce an intermediate hydrolyzate comprising 2-hydroxy-4-(methylthio)butanamide; and | CSCCC(O)C(N)=O | null | null | null |
909,162 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [OH:1][NH:2][C:3](=[NH:30])[C:4]1[CH:29]=[CH:28][C:7]([CH2:8][N:9]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[C:31](O)(=[O:43])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41... | CCCCCCCCCCCC(=O)O | CC(C)(C)OC(=O)N(Cc1ccc(C(=N)NO)cc1)Cc1ccc(C(F)(F)F)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 | The same procedure as employed in the preparation of Example 10 (step a) but using tert-butyl 4-[(hydroxyamino)(imino)methyl]benzyl[4-(trifluoromethyl)benzyl]carbamate and dodecanoic acid gave the title compound as a colorless oil (95%). 1H NMR (CD3OD, 300 MHz) δ 7.68 (d, 2H, J=7.9 Hz), 7.59 (d, 2H, J=8.0 Hz), 7.27 (m,... | CCCCCCCCCCCC(=O)ONC(=N)c1ccc(CN(Cc2ccc(C(F)(F)F)cc2)C(=O)OC(C)(C)C)cc1 | null | 95 | null |
798,889 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | C(N(CC)C(C)C)(C)C.Cl[C:11]([O:13][CH3:14])=[O:12].[F:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]1[CH2:27][NH:26][CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=1>ClCCl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]1[CH2:27][N:26]([C:11]([O:13][CH3:14])=[O:12])[CH:25]([... | COC(=O)Cl | Fc1ccc(F)c(C2=CC(c3ccccc3)NC2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | N,N-Diisopropylethylamine (0.19 mL, 1.1 mmol, 6.0 equiv) and methyl chloroformate (0.014 uL, 0.18 mmol, 1.0 equiv) were added to a solution of 4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole (1-5, 0.18 mmol, 1 equiv) in dichloromethane (10 mL) at 23° C., and the resulting mixture was stirred for 1 hour, then con... | COC(=O)N1CC(c2cc(F)ccc2F)=CC1c1ccccc1 | null | null | null |
1,760,424 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | C([N:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](=[O:26])[NH:16][C:15]1=[O:27])(C1C=CC=CC=1)C1C=CC=CC=1.OS(C(F)(F)F)(=O)=O>C(O)(C(F)(F)F)=O>[C:20]1([C:18]2[C:17](=[O:26])[NH:16][C:15](=[O:27])[NH:14][CH:19]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1 | O=c1[nH]c(=O)n(C(c2ccccc2)c2ccccc2)cc1-c1ccccc1 | null | 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 | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 0 | 2 | 1-Benzhydryl-5-phenyl-pyrimidine-2,4-dione (0.13 g, 0.35 mmol) was added to solution of triflic acid (0.09 mL, 0.99 mmol) in TFA (0.87 mL) cooled to 0° C. The reaction mixture was stirred for 2 hrs and then quenched by addition of ice. The white precipitate was filtered and dried. The filtrate was diluted with EtOAc an... | O=c1[nH]cc(-c2ccccc2)c(=O)[nH]1 | null | null | null |
1,619,989 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][C:18](OCC)=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][C... | CCOC(=O)Cc1cnc2cc(OCc3cccc(Cl)c3)ccc2c1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 7 | To a cooled, −78° C., solution of ethyl 2-(7-((3-chlorobenzyl)oxy)quinolin-3-yl)acetate (Example 51, 50 mg, 0.14 mmol) in THF (1.5 mL), under an atmosphere of nitrogen, was added LiAlH4 (2.4 M in THF, 0.1 mL, 0.24 mmol). The reaction was stirred for 7 h before being quenched with 1N NaOH (aq.). The crude reaction mixtu... | OCCc1cnc2cc(OCc3cccc(Cl)c3)ccc2c1 | null | 66 | null |
445,662 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([F:14])[CH:6]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O>>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH:5]([CH2:13][CH3:12])[CH2:6][CH3:7])=[O:10])=[C:7]([F:14])[CH:6]=1)(=[O:3])[CH3:2] | CC(=O)Oc1ccc(C(=O)O)c(F)c1 | null | null | null | 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 | 25 | 24 | 1.0 Gram of 4-acetoxy-2-fluorobenzoic acid was added to 7 ml of thionyl chloride, and the mixture was allowed to react under reflux for 5 hours. Thereafter, excessive thionyl chloride was distilled off, and a mixture comprising 1 ml of pyridine, 4 ml of dry ether and 0.6 g of 3-pentanol was added dropwise to the above ... | CCC(CC)OC(=O)c1ccc(OC(C)=O)cc1F | null | null | null |
932,658 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O/[N:30]=[C:31](\[NH2:39])/[CH2:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1>CN(C=O)C>[N:35]1[CH:36]=[CH:37][CH:38]=[C:33]([CH2:32][C:31]2[N:39]=[C:14]([CH:11]3[CH2:10][CH2:9]... | N/C(Cc1cccnc1)=N\O | CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1 | null | O=C(n1ccnc1)n1ccnc1 | 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 | 70 | 6 | 1-(Tert-butoxycarbonyl)piperidine-4-carboxylic acid (2.29 g, 0.010 mmol) was treated with 1,1′-carbonyldiimidazole (1.62 g, 0.010 mmol) in DMF (5 mL) at ambient temperature for 30 min. Following this activation period, the crude (1Z)-N′-hydroxy-2-pyridin-3-ylethanimidamide (0.010 mmol) was added and the reaction mixtur... | CC(C)(C)OC(=O)N1CCC(c2nc(Cc3cccnc3)no2)CC1 | null | null | null |
813,494 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH2:14])[CH2:10][C@H:9]1[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:28]([CH:22]... | CC(C)(C)OC(=O)N1C[C@@H](CN)C[C@H]1C(=O)N1CCCC1 | O=C(Cl)C1CCCCC1 | 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 | 25 | 12 | To a stirred solution of (2S, 4R)-4-aminomethyl-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.51 mmol, Example 39C) in dichloromethane (2 mL) at room temperature was added cyclohexanecarbonyl chloride (0.092 g, 0.65 mmol) and triethylamine (0.10 mL, 0.75 mmol). The mixture was stir... | CC(C)(C)OC(=O)N1C[C@@H](CNC(=O)C2CCCCC2)C[C@H]1C(=O)N1CCCC1 | null | null | null |
1,502,536 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:29]1[C:34]([C:35]#[N:36])=[CH:33][CH:32]=[CH:31][N:30]=1.O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[... | N#Cc1cccnc1Cl | CC(C)(C)OC(=O)N1CCN(Cc2cccc(O)c2)CC1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 60 | null | To a solution of 4-(3-hydroxy-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (300 mg, 1.0 mmol) in DMSO (5.0 mL) were added Cs2CO3 (660 mg, 2.0 mmol) and 2-chloro-3-pyridinecarbonitrile (172 mg, 1.2 mmol). The mixture was heated at 60° C. for 90 min. The reaction mixture was cooled to rt, poured into water, and ... | CC(C)(C)OC(=O)N1CCN(Cc2cccc(Oc3ncccc3C#N)c2)CC1 | null | 58.1 | null |
307,191 | ord_dataset-a6643d22de674f30a85ba57198b82644 | null | 1995-01-01T00:03:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]2=[O:21])([O-])=O>Cl>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]2=[O:21] | O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1Cc1cccnc1 | null | 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 | 25 | 0.25 | To 200 ml of conc. hydrochloric acid was added 21.1 g of stannous chloride under ice cooling, and 9.0 g of 5-nitro-2-(3-pyridylmethyl)-1H-isoindole-1,3 (2H)-dione was added. The reaction mixture was stirred at room temperature for 15 minutes and stirred at 80° C. for 30 minutes. After cooling, the mixture was filtered,... | Nc1ccc2c(c1)C(=O)N(Cc1cccnc1)C2=O | null | 92 | null |
272,075 | ord_dataset-347c0709d28a44dea43ca42052be4db3 | null | 1993-01-01T00:07:00 | true | [CH3:1][S:2]([C:5]1[C:6]2[C:7]3[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]=3[CH:15]=[CH:16][CH:17]=2)(=[O:4])=[O:3].[H-].[Na+].Br[CH:21]([CH3:23])[CH3:22]>CN(C)C=O>[CH3:22][CH:21]([N:10]1[C:11]2[C:7]3[C:6](=[CH:17][CH:16]=[CH:15][C:8]=3[C:9]1=[O:14])[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:13][CH:12]=2)[CH3:23] | CS(=O)(=O)c1ccc2c3c(cccc13)C(=O)N2 | CC(C)Br | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2.5 g of 6-(methylsulfonyl)-benz[cd]indol-2(1H)-one (Example 3), 0.6 g of sodium hydride and 2.7 ml of 2-bromopropane in 100 ml of N,N-dimethylformamide is reacted for 18 hours under argon using the conditions of Example 4 to yield 2.24 g of the desired product as a yellow solid, m.p. 164°-165° C. | CC(C)N1C(=O)c2cccc3c(S(C)(=O)=O)ccc1c23 | null | null | null |
408,408 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | [CH2:1]([O:3][C:4](=[O:35])[CH2:5][NH:6][S:7]([C:10]1[S:11][C:12]([C:15]#[C:16][C:17]2[CH:34]=[N:33][C:20]3[N:21]=[C:22]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[N:23]=[C:24]([OH:25])[C:19]=3[CH:18]=2)=[CH:13][CH:14]=1)(=[O:9])=[O:8])[CH3:2]>C(O)(=O)C.[Pt]=O>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][NH:6][S:7... | CCOC(=O)CNS(=O)(=O)c1ccc(C#Cc2cnc3nc(NC(=O)C(C)(C)C)nc(O)c3c2)s1 | null | null | O=[Pt] | 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 | 24 | To a mixture of 150 mg of N-[5-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-ylethynyl)thien-2-ylsulfonyl]glycine ethyl ester in 25 mL of glacial acetic acid was added 100 mg of platinum oxide. This mixture was stirred under hydrogen for 24 hours and an additional 100 mg of platinum oxide was added. The hydrogenat... | CCOC(=O)CNS(=O)(=O)c1ccc(CCC2CNc3nc(NC(=O)C(C)(C)C)nc(O)c3C2)s1 | null | 31.5 | null |
1,289,718 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | CS(O[CH2:6][C@H:7]1[CH2:12][N:11]([S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)(=O)=O.CO.[NH3:36]>>[NH2:36][CH2:6][C@H:7]1[CH2:12][N:11]([S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2... | CC(O)(c1ccc(N2CCN(S(=O)(=O)c3cccs3)C[C@@H]2COS(C)(=O)=O)cc1)C(F)(F)F | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 140 | null | A mixture of ((2R)-4-(thiophen-2-ylsulfonyl)-1-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)piperazin-2-yl)methyl methanesulfonate (0.9 g, 1.70 mmol, Intermediate B) in 2 M NH3 in MeOH (10 mL, 20.0 mmol) was heated in an Initiator microwave reactor (Biotage AB, Inc., Uppsala, Sweden) at 140° C. for 30 min. The mixtu... | CC(O)(c1ccc(N2CCN(S(=O)(=O)c3cccs3)C[C@@H]2CN)cc1)C(F)(F)F | null | null | null |
428,717 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [CH3:1][N:2]([CH2:4][CH2:5][C:6]([P:12](=[O:15])([OH:14])[OH:13])([P:8](=[O:11])([OH:10])[OH:9])[OH:7])[CH3:3].[OH-].[Na+:17]>>[Na+:17].[CH3:1][N:2]([CH2:4][CH2:5][C:6]([P:8](=[O:9])([OH:11])[O-:10])([P:12](=[O:13])([OH:14])[OH:15])[OH:7])[CH3:3] | CN(C)CCC(O)(P(=O)(O)O)P(=O)(O)O | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Add with constant stirring 11,11 kg of (II) to 33.3 l sodium hydroxide (50,7 g/l). Filter if necessary, add 122 l of methanol and dry in an oven with forced air circulation until constant weight. 10.7 kg of (III) is obtained. | CN(C)CCC(O)(P(=O)([O-])O)P(=O)(O)O | null | null | null |
1,244,846 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH3:1][N:2]([CH3:24])[C:3]1[N:23]=[C:6]2[CH:7]=[C:8]([NH:11][C:12]([C:14]3[N:18]([CH3:19])[N:17]=[CH:16][C:15]=3[C:20](O)=[O:21])=[O:13])[CH:9]=[CH:10][N:5]2[N:4]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:1][N:2]([CH3:24])[C:3]1[N:23]=[C:6]2[CH:7]=[C:8]([NH:11][C:12]([C:14]3... | C1CCNC1 | CN(C)c1nc2cc(NC(=O)c3c(C(=O)O)cnn3C)ccn2n1 | null | CCCP(=O)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 70 | 18 | A mixture of 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (150 mg, 455 μmol), pyrrolidine (226 μl, 2.73 mmol), propylphosphonic anhydride (50% in ethyl acetate, 671 μl, 1.14 mmol) and diisopropylethylamine (239 μl, 1.37 mmol) in tetrahydrofurane (8 ml) is stir... | CN(C)c1nc2cc(NC(=O)c3c(C(=O)N4CCCC4)cnn3C)ccn2n1 | null | 89.1 | null |
921,368 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][C:24]3[S:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[Cl:29][C:26]1[S:25][C:24]([CH2:23][N:16]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:22]3[C:14]([CH:11]3[CH2:10][CH... | CC(C)(C)OC(=O)N1CCC(c2cn(Cc3ccc(Cl)s3)c3ncccc23)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 1 | Over a solution of 2.86 g (6.6 mmol) of 4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester in 20 ml of dichloromethane, 5.1 ml of trifluoroacetic acid were added. After 1 hour at room temperature, the solvent was removed under reduced pressure. The crude mixt... | Clc1ccc(Cn2cc(C3CCNCC3)c3cccnc32)s1 | null | 127.8 | null |
928,793 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C[CH:13]([C@@H:17]1[CH2:22][CH2:21][NH:20][C@H:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH2:18]1)[C:14]([O-:16])=[O:15]>>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([CH:19]([C:23]2[CH:24]=[CH:25][C:26]([... | FC(F)(F)c1ccc(Br)cc1 | CC(C(=O)[O-])[C@@H]1CCN[C@H](c2ccc(C(F)(F)F)cc2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The compound was prepared analogously to Example 160 using the Grignard reagent derived from 4-brombenzotrifluoride and starting with the chiral piperidine of Example 114 Step 1. M/Z (ES+) 590 (M+H). | O=C(O)C[C@@H]1CCN(C(c2ccc(C(F)(F)F)cc2)c2ccc(C(F)(F)F)cc2)[C@H](c2ccc(C(F)(F)F)cc2)C1 | null | null | null |
1,032,023 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:3]=1[C:4]([NH:6][C@@H:7]([CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:27])[C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:16][CH:15]=1)[C:8]([OH:10])=[O:9])=[O:5].[OH-].[Na+:34]>CO>[Na+:34].[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:3... | CN(c1ccc(/C=C/C[C@H](NC(=O)c2c(Cl)cccc2Cl)C(=O)O)cc1)c1ncccn1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 0.08 | To a solution of (S,E)-2-(2,6-dichlorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid (10.60 g) in methanol (200 ml), 1N aqueous sodium hydroxide solution (22.5 ml) was added, and the resulting mixture was stirred at room temperature for 5 minutes. The reaction solution was concentrated to dryness ... | CN(c1ccc(/C=C/C[C@H](NC(=O)c2c(Cl)cccc2Cl)C(=O)[O-])cc1)c1ncccn1 | null | null | null |
1,291,944 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cl:13]N1C(=O)CCC1=O>CC#N>[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([Br:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2 | Nc1ccc(Br)c2cccnc12 | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 75 | null | To a solution of 8-amino-5-bromoquinoline (440 mg, 1.97 mmol) in CH3CN (39 mL) was added N-chlorosuccinimide (250 mg, 1.87 mmol). The mixture was stirred at 75° C. until no further conversion of the starting material was observed by LC/MS and TLC analysis. The mixture was allowed to cool to room temperature then concen... | Nc1c(Cl)cc(Br)c2cccnc12 | null | null | null |
260,160 | ord_dataset-ab5ba9f863cb41d9924be0bb3c730818 | null | 1993-01-01T00:01:00 | true | [C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14](F)=[CH:13][C:12]=2F)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:20]([CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([N:30]3[... | c1ccc(CC2CCNCC2)cc1 | CC(=O)N1CCC(C(=O)c2ccc(F)cc2F)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 | 100 | 24 | A mixture consisting of 2.67 g of 1-acetyl-4-(2,4-difluorobenzoyl)piperidine and 8.8 ml of 4-benzylpiperidine was stirred at 100° C. for 24 hours and the reaction mixture was then worked up in the same manner as Example 2 to give 4.1 g of the title compound as oil. | CC(=O)N1CCC(C(=O)c2ccc(N3CCC(Cc4ccccc4)CC3)cc2N2CCC(Cc3ccccc3)CC2)CC1 | null | null | null |
528,775 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][CH:11]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=2)[CH3:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][CH:11]([C:21]2[CH:22]=[CH:23][C:24](... | COc1ccc(C(N[C@H](C)c2ccc(F)cc2)c2cccc([N+](=O)[O-])c2)cc1 | null | null | Cl[Ni]Cl | [BH4-] | [Na+] | 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 | Following a similar reaction, separation and purification procedure to that described in Example (59b), 7.60 g of N-[(R)-1-(4-fluorophenyl)ethyl]-N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]amine [prepared as described in step (a) above], 9.51 g of nickel chloride hexahydrate and 3.03 g of sodium borohydride were reacte... | COc1ccc(C(N[C@H](C)c2ccc(F)cc2)c2cccc(N)c2)cc1 | null | null | null |
1,015,548 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].S(O)(O)(=O)=O.[NH2:17][OH:18].[OH-].[Na+]>C(O)C>[C:6]1([C:2]2[CH:3]=[C:4]([NH2:5])[O:18][N:17]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1 | NO | N#CCC(=O)c1ccccc1 | null | O=S(=O)(O)O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 3-oxo-3-phenylpropanenitrile (5.00 g, 34.4 mmol), hydroxylamine sulfate (3.10 g, 18.9 mmol), ethanol (35 ml) and an aqueous solution (35 ml) of sodium hydroxide (1.66 g, 41.4 mmol) was stirred at 80° C. for 24 hours. After cooling to room temperature, the reaction mixture was adjusted to pH=11 by addition ... | Nc1cc(-c2ccccc2)no1 | null | 36 | null |
192,809 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | Cl[CH2:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:4]1=[O:16].[I-:17].[Na+]>CC(C)=O>[I:17][CH2:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:4]1=[O:16] | O=C1CC(CCl)C(=O)N1c1ccc(F)cc1 | [I-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 15.2 g (0.06 moles) 3-chloromethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione (according to Example 1) and 10.7 g (0.066 moles) sodium iodide in acetone were refluxed for 8 hours in acetone. The precipitated sodium chloride was then filtered off, and the filtrate was concentrated, extracted with chloroform ... | O=C1CC(CI)C(=O)N1c1ccc(F)cc1 | null | 92 | null |
234,125 | ord_dataset-45d20d09e4d64f45bdd419044025b4d3 | null | 1991-01-01T00:09:00 | true | Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10]([O:29][CH3:30])[CH2:11][S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:7])=[O:6].[I-:31].[Na+]>C(C(C)=O)C>[CH2:13]([S:12][CH2:11][CH:10]([O:29][CH3:30])[CH2:9][NH:8][S:5]([CH2:4]... | CCCCCCCCCCCCCCCCSCC(CNS(=O)(=O)CCCCl)OC | [I-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1.03 g (2.12 mM) of 3-(3-chloropropylsulfonylamino)-1-hexadecylthio-2-methoxypropane IIIa2 in 20 ml of methyl ethyl ketone is added 636 mg (4.24 mM) of sodium iodide and the mixture is refluxed or 3 hours with stirring. After the solvent is evaporated, the residue is purified by the column chromatograp... | CCCCCCCCCCCCCCCCSCC(CNS(=O)(=O)CCCI)OC | null | 86.6 | null |
794,048 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:14][CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[C:9]([N+:11]([O-])=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>CC(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:14][CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[C:9]([CH:10]=1)[NH2:11])([CH3:4])([CH3:3]... | CCCCC(CC)CSc1ccc(C(C)(C)C)cc1[N+](=O)[O-] | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | In a typical example of a specific production method, ferric chloride hexahydrate and an activated carbon are added to a 2-propanol solution of 5-tert-butyl-2-(2-ethylhexylthio)nitrobenzene, and the mixture is refluxed under heating for 10 minutes. To this solution is added, dropwise, an aqueous 80% solution of hydrazi... | CCCCC(CC)CSc1ccc(C(C)(C)C)cc1N | null | null | null |
994,232 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7]([NH:9][CH:10]1[CH2:12][CH2:11]1)=[O:8].[CH3:15][O:16][CH2:17]/[CH:18]=[CH:19]/B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+].Cl>CN(C=O)C.C(O)CC>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([CH:19]=[CH:18][CH2:17][O:16][CH3:15])=[CH:13][C:6]=1[C:7]([NH:9][CH:10]1[CH2:12][CH2... | COC/C=C/B1OC(C)(C)C(C)(C)O1 | O=C(NC1CC1)c1cc(Br)ccc1Cl | null | Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCCO | null | null | null | null | null | null | null | null | null | 80 | 2 | 5-Bromo-2-chloro-N-cyclopropyl-benzamide (19.3 g, 70.5 mmol) was dissolved in a mixture of DMF (350 mL) and 1-propanol (210 mL). Pd(OAc)2(PPh3)3 (2.64 g, 3.53 mmol) was added. (E)-2-(3-Methoxypropenyl)4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15 mL, 70.5 mmol) was added through a syringe, and aq. 2M Na2CO3 (123 mL) was ... | COCC=Cc1ccc(Cl)c(C(=O)NC2CC2)c1 | null | 67.8 | null |
661,505 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[C:13](Cl)[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:5]1=[O:22])(=O)C.[CH3:23][N:24]([CH2:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)[CH3:25].[OH-].[Na+]>CN(C=O)C.CO>[CH3:25][N:24]([CH2:26][C:27]1[CH:33]=[CH:32][C:30]([NH:31]/[C:... | CN(C)Cc1ccc(N)cc1 | CC(=O)N1C(=O)C(=C(Cl)c2ccc(C)cc2)c2ccccc21 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CO | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 2 from 1-acetyl-3-[1-chloro-1-(p-tolyl)-methylidene)-2-indolinone and 4-dimethylaminomethyl-aniline in DMF and subsequent treatment with sodium hydroxide solution in methanol. | Cc1ccc(/C(Nc2ccc(CN(C)C)cc2)=C2/C(=O)Nc3ccccc32)cc1 | null | null | null |
1,314,427 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:20]3[CH2:23][CH2:22][CH2:21]3)=[N:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14](F)=[C:15]([CH:18]=2)C#N)[CH:5]=[CH:6][N:7]=1.[OH:24]OB(C1C=CC=CC=1)O>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:20]3[CH2:23][CH2:22][CH2:21]3)=[N:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([OH:24])=[CH:15][CH:18]=2)[CH:5]=[... | N#Cc1cc(-c2nc(C3CCC3)n3ccnc(N)c23)ccc1F | OOB(O)c1ccccc1 | null | null | null | null | null | null | null | 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 a Suzuki coupling procedure analogous to that described for synthesis of 5-(8-amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)-2-fluorobenzonitrile, except using 4 hydroxyphenylboronic acid. MS (ES+): m/z 281.17 (100)[MH+]. | Nc1nccn2c(C3CCC3)nc(-c3ccc(O)cc3)c12 | null | null | null |
793,609 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[C:17]([F:18])[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[CH2:24]>>[F:18][C:17]1[C:12]2[N:13]([C:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([C:28]4[CH:29]=[CH:30]... | CC(C)(O)c1ccn2c(-c3ccc(F)c(Cl)c3)cnc2c1F | C=Cc1ccc(B(O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]-propan-2-ol and 4-vinylbenzeneboronic acid were coupled in the same way as in Example 30 to give 2-[8-fluoro-3-(2-fluoro-4′-vinylbiphenyl-5-yl)-imidazo[1,2-α]pyridin-7-yl]propan-2-ol as an off-white solid (3 mg, 3%): m/z (ES+) 391 [MH+]. | C=Cc1ccc(-c2cc(-c3cnc4c(F)c(C(C)(C)O)ccn34)ccc2F)cc1 | null | 3 | null |
508,702 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | O.[OH-].[Li+].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11]([CH3:41])=[C:12]([CH2:14][O:15][C:16]2[CH:40]=[CH:39][C:19]([CH2:20][O:21]/[N:22]=[C:23](/[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)\[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:18][CH:17]=2)[N:13]=1.O.Cl>O1CCCC1>[O:4]1[CH:8]=[CH:7][C... | CCOC(=O)CCCC/C(=N\OCc1ccc(OCc2nc(-c3ccco3)oc2C)cc1)c1ccccc1 | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 4 | Lithium hydroxide monohydrate (163 mg) was added to a solution of ethyl E-6-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxyimino]-6-phenylhexanoate (670 mg) in tetrahydrofuran (6 ml)-water (4 ml)-etbanol (4 ml) and stirred at room temperature for 4 hours. 1N hydrochloric acid (3.9 ml) was added to the reaction mix... | Cc1oc(-c2ccco2)nc1COc1ccc(CO/N=C(\CCCCC(=O)O)c2ccccc2)cc1 | null | 98.6 | null |
1,679,168 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [H-].C([Al+]CC(C)C)C(C)C.[N+:11]([C:14]1[C:19]2[NH:20][C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)([C:24]#[N:25])[CH2:22][O:23][C:18]=2[CH:17]=[CH:16][CH:15]=1)([O-:13])=[O:12]>C1(C)C=CC=CC=1>[N+:11]([C:14]1[C:19]2[NH:20][C:21]([CH2:24][NH2:25])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:22][O:23][C:18... | N#CC1(c2ccccn2)COc2cccc([N+](=O)[O-])c2N1 | null | null | CC(C)C[Al+]CC(C)C | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 0.17 | 1.0 M Diisobutylaluminum hydride in toluene (200 μL, 0.2 mmol) was added drop-wise to a solution of 5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carbonitrile (50 mg, 0.2 mmol) (Example 71, Step 1), in toluene (5 mL) at room temperature. The reaction mixture was stirred for 10 min, then quenched with methanol... | NCC1(c2ccccn2)COc2cccc([N+](=O)[O-])c2N1 | null | 87.3 | null |
716,458 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [CH3:1][CH:2]([CH3:34])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][C:22](=O)[C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH2:14][CH2:13]2)[CH:7]=1)=[O:4].[C:35]1([NH:41]N)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH3:1][CH... | CC(C)C(=O)Nc1cccc(C2CCN(CCCCC(=O)c3ccc(C(F)(F)F)cc3)CC2)c1 | NNc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by Procedure E and Scheme M using 2-methyl-N-[3-(1-{5-oxo-5-[4-(trifluoromethyl)phenyl]pentyl}-4-piperidinyl)phenyl]propanamide and phenylhydrazine: ESMS m/e: 548.2 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(CCCc3c(-c4ccc(C(F)(F)F)cc4)[nH]c4ccccc34)CC2)c1 | null | null | null |
1,322,362 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][NH2:11].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][N:23]([C:26]2[S:27][C:28]([C:32](O)=[O:33])=[C:29]([CH3:31])[N:30]=2)[C:22](=[O:35])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[... | Cc1nc(-n2ccc(OCc3ccccc3)cc2=O)sc1C(=O)O | NCc1cc2ccccc2[nH]1 | null | null | null | null | null | null | null | 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 as described in Example 22, making variation only as required to use (1H-indol-2-yl)methanamine in place of benzo[b]thiophen-2-ylmethanamine to react with 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 22% yield... | Cc1nc(-n2ccc(OCc3ccccc3)cc2=O)sc1C(=O)NCc1cc2ccccc2[nH]1 | null | 22 | null |
1,738,504 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:10][C:4]=2[CH:3]=1.Br[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C.[Cu]I>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[N:10]([C:18]3... | Cn1cc(-c2cc3cnc(Br)cc3[nH]2)cn1 | Brc1ncccn1 | null | [Cu]I | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 210 | null | 6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 27 mg 0.10 mmole) and 2-bromopyrimidine (24 mg, 0.15 mmole) were dissolved in DMA (0.7 ml) and potassium carbonate (20 mg, 0.14 mmole) and copper(I) iodide (4.0 mg, 0.022 mmole) were added. The reaction was placed under argon and heated by ... | Cn1cc(-c2cc3cnc(Br)cc3n2-c2ncccn2)cn1 | null | 87.3 | null |
1,694,184 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[C:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH:21]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([CH:... | CC(C)(C)OC(=O)N1CC=C(c2cc(=O)[nH]c3ccc(C(c4ccc(Cl)cc4)c4ccc(Cl)cc4)cc23)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of tert-butyl 4-(6-(bis(4-chlorophenyl)methyl)-2-oxo-1,2-dihydroquinolin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate (80 mg, 0.142 mmol) in DCM (1 mL) was added TFA (0.35 mL) and the resulting mixture was stirred at room temperature for 2 hr. The reaction was concentrated and dried under the high vacuum t... | O=c1cc(C2=CCNCC2)c2cc(C(c3ccc(Cl)cc3)c3ccc(Cl)cc3)ccc2[nH]1 | null | null | null |
74,488 | ord_dataset-b9d8ddf9c2884d40859b6b5f24815a7d | null | 1980-01-01T00:12:00 | true | C(=O)([O-])OCC[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1>[Pd].C(O)(=O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][OH:13])=[CH:7][CH:8]=1 | O=C([O-])OCCC(=O)c1ccc(Cl)cc1 | null | null | [Pd] | 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 | 10 | 100 ml of glacial acetic acid and 5 g of 5% Pd on C are added to a solution of p-chlorobenzoyl-ethyl carbonate (22.8 g=0.1 moles). The mixture is reduced in a PARR apparatus for 10 hours at 60° and under a pressure of 200 psi (14 atm) of H2. We proceed as in Example II. We obtain 11.7 g (82%) of a product having the fo... | OCc1ccc(Cl)cc1 | null | 82.1 | null |
222,408 | ord_dataset-42629b4cf1094978a5e5f29f22639ee7 | null | 1991-01-01T00:01:00 | true | C1CO[C:3]2([CH2:15][C:14]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[CH2:5][CH2:4]2)[O:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:5]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH2:15][C:3](=[O:2])[CH2:4]1 | c1ccc2c3c([nH]c2c1)CCC1(C3)OCCO1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | 165 g (0.72 mol) of 3,3-ethylenedioxy-1,2,3,4-tetrahydrocarbazole are dissolved in 2 l of acetone, and 3 g of p-toluenesulphonic acid are added. After the reaction solution has been heated under reflux for 4 h it is concentrated, 2 l of ethyl acetate are added, and the mixture is extracted 3 times with 1 l of saturated... | O=C1CCc2[nH]c3ccccc3c2C1 | null | null | null |
78,475 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:18]=[CH:17][C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[C:10]=1[C:19](Cl)=[O:20]>C(C(C)=O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[NH:1][C:19]([C:10]1[C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=[CH:18][C:9]=1[Cl:8])=[O:20] | O=C(Cl)c1c(Cl)ccc2c1OCCO2 | Nc1ncccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | 10 | 2 | 280 ml of methyl ethyl ketone, 13 g of 2-amino-pyrimidine were put into a 500 ml balloon flask provided with a stirrer and a thermometer. The mixture was cooled to 10° C. and 28 g of ground 6-chloro-1,4-benzodioxane-5-carbonyl chloride was added and stirred for two hours, the temperature being allowed to rise to 20° C.... | O=C(Nc1ncccn1)c1c(Cl)ccc2c1OCCO2 | null | null | null |
948,442 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:11]=1[O:25]CC1C=CC=CC=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>CO.[Pd]>[CH2:6]([O:5][P:4]([CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:... | CCOP(=O)(Cc1cc(Cc2ccc(CC)cc2)ccc1OCc1ccccc1)OCC | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 5 | To a solution of [2-benzyloxy-5-(4-ethylbenzyl)benzyl]phosphonic acid diethylester (1.03 g) in methanol (10.0 mL) was added 5% Pd—C (0.10 g), and the reaction mixture was stirred for 5 hr at room temperature under hydrogen gas atmosphere. After filtration and evaporation, the residue was purified by silica gel column c... | CCOP(=O)(Cc1cc(Cc2ccc(CC)cc2)ccc1O)OCC | null | 97 | null |
825,232 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.[CH2:23]([O:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([O:30][C:31]1[CH:32]=[C:33]([NH:34][C:2... | Nc1cccc(OCc2ccccc2)c1 | Cc1nnc(-c2ccc(C)c(-c3ccc(C(=O)O)cc3)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 | N-(3-Benzyloxyphenyl)-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide was prepared from 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid and 3-benzyloxyaniline using method I. LCMS; retention time 3.79 min, MH+ 476. | Cc1nnc(-c2ccc(C)c(-c3ccc(C(=O)Nc4cccc(OCc5ccccc5)c4)cc3)c2)o1 | null | null | null |
12,105 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | Cl[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][O:7][CH:8]([CH3:10])[CH3:9].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][SH:17])=[CH:14][CH:13]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH:8]([O:7][CH2:6][CH2:5][CH:4]=[CH:3][CH2:2][S:17][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=1)([CH3:10])[CH3:9] | SCc1ccc(Cl)cc1 | CC(C)OCCC=CCCl | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | null | 1 | 8.1 g (0.05 mol) of 1-chloro-5-isopropoxy-2-pentene are added dropwise at 20-25° during the course of 10 minutes and while stirring to a solution of 7.9 g (0.05 mol) of 4-chloro-benzylmercaptan and 5.6 g (0.05 mol) of potassium tert.butoxide in 150 cc of tert.butanol. The solution which is rendered turbid during the ad... | CC(C)OCCC=CCSCc1ccc(Cl)cc1 | null | null | null |
1,483,643 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [F:1][C:2]([F:38])([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:36]=[CH:35][C:22]4[N:23]([CH2:27][O:28]CC[Si](C)(C)C)[C:24](=[O:26])[O:25][C:21]=4[CH:20]=3)=[CH:13][N:12]=2)=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:28][CH2:27][N:23]1[C:22]2[CH:35]=[CH:36][C:19]([O:... | C[Si](C)(C)CCOCn1c(=O)oc2cc(OCc3cnc(Nc4ccc(OC(F)(F)F)cc4)nc3)ccc21 | 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 | 18 | To a solution of 6-((2-((4-(trifluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]oxazol-2(3H)-one (0.05 g, 0.091 mmol) in DCM (3 mL) at 0° C., TFA (0.035 mL, 0.456 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. Solvent was removed under vacuu... | O=c1oc2cc(OCc3cnc(Nc4ccc(OC(F)(F)F)cc4)nc3)ccc2n1CO | null | 61.3 | null |
770,899 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:21]=[CH... | O=S(=O)(c1ccccc1)c1ccc(/C=C/c2ccc(F)cc2F)cc1 | null | null | [Pd] | 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 | 2 | 2,4-Difluoro-1-{(E)-2-[4-(phenylsulfonyl)phenyl]vinyl}benzene (Example 51, 57 mg, 0.16 mmol) and palladium (10% wt. on activated carbon, 20 mg) were combined in ethyl acetate (20 mL) and shaken in a Parr apparatus for 2 hours. The catalyst was removed by filtration and the filtrate evaporated in vacuo. The residue was ... | O=S(=O)(c1ccccc1)c1ccc(CCc2ccc(F)cc2F)cc1 | null | 40.1 | null |
713,396 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [N:1]([CH:4]([CH2:12][F:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+]=[N-]>CO.[Pd]>[F:13][CH2:12][CH:4]([NH2:1])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1 | [N-]=[N+]=NC(CF)Cc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of (2-azido-3-fluoro-propyl)benzene (0.6 g) in MeOH (50 mL) was added 10% Pd/C catalyst and the suspension was hydrogenated for 2 h at 3 atmospheres pressure. The filtered reaction mixture and MeOH washings were concentrated to an oil which was chromatographed over silica gel with an ammoniated mixture of... | NC(CF)Cc1ccccc1 | null | 74.1 | null |
1,627,086 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[NH:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[CH2:25][C@H:14]12.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>>[N:13]1([C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)... | c1ccc2c(c1)C[C@@H]1NCCC[C@H]21 | O=C(O)c1ccc2[nH]ncc2c1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 1H-indazole-5-carboxylic acid and cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine following a procedure analogous to that described in Example 1 [2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate is used]. Yield: 31% of theory; LC (method 4): tR=1.91 ... | O=C(c1ccc2[nH]ncc2c1)N1CCC[C@@H]2c3ccccc3C[C@@H]21 | null | 31 | null |
1,125,453 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH3:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.I[CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:9][CH2:14][CH3:15])=[CH:6][C:7]=1[F:8] | CCI | Cc1cc([N+](=O)[O-])c(O)cc1F | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 4-Methyl-5-fluoro-2-nitrophenol (11.1 g, 65.0 mmol) and iodoethane (12.2 g, 78.0 mmol) were dissolved in 100 mL of DMSO with stirring. K2CO3 (13.5 g, 97.5 mmol) was added. The reaction was stirred for 3 h and then diluted with DCM and filtered. The filtrate was poured into H2O and extracted with DCM. The combined organ... | CCOc1cc(F)c(C)cc1[N+](=O)[O-] | null | 60.6 | null |
888,355 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12]/[C:11](=[C:19]3/[C:20]([CH2:25][CH2:26][CH3:27])=[N:21][NH:22][C:23]/3=[O:24])/[CH:10]=2)=[CH:4][CH:3]=1.[CH:28]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[O:24]=[C:23]1[NH:22][N:21]=[C:20]([CH2:25][CH2:... | O=C(Cl)C1CCCC1 | CCCC1=NNC(=O)/C1=C1/C=C(Sc2ccc(N)cc2)c2ccccc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized using (Z)-4-(4-(4-aminophenylthio)quinolin-2(1H)-ylidene)-3-propyl-1H-pyrazol-5(4H)-one and cyclopentanecarbonyl chloride in THF according to the procedure described in the synthesis of Example 26. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.69 (t, J=7.33 Hz, 3H) 1.32 (dq, J=14.97, 7.39 Hz, 2H)... | CCCC1=NNC(=O)/C1=C1/C=C(Sc2ccc(NC(=O)C3CCCC3)cc2)c2ccccc2N1 | null | null | null |
1,758,456 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[NH2:12][C:13]([CH:17]([F:19])[F:18])=[CH:14][C:15]#[N:16]>C(O)(=O)C.C1COCC1>[F:18][CH:17]([F:19])[C:13]1[NH:12][C:13]([CH:17]([F:19])[F:18])=[C:14]([C:15]#[N:16])[CH:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[C:14]=1[C:15]#[... | N#CC=C(N)C(F)F | O=Cc1ccc2[nH]ncc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 80 mg (0.55 mmol) 1H-indazole-5-carbaldehyde, 142 mg (1.21 mmol) 3-amino-4,4-difluorobut-2-enenitrile [obtainable by Thorpe reaction of acetonitrile with 2,2-difluoroacetonitrile, cf. Org. React. 15, 1 (1967), ibid. 1 (1984)] and a trace amount of powdered 4 Å molecular sieve in acetic acid (0.53 ml) was h... | N#CC1=C(C(F)F)NC(C(F)F)=C(C#N)C1c1ccc2[nH]ncc2c1 | null | null | null |
22,486 | ord_dataset-19b9e29d593f4660ab77c07b459da9bb | null | 1977-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.[C:21]([OH:26])(=[O:25])[C:22]([CH3:24])=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[C:22]([C:21]([OH:26])=[O:25])[CH3:24])[CH2:9][N:8]=[C:7]([C:14]3[... | CC(=O)C(=O)O | NNC1=Nc2ccc(Cl)cc2C(c2ccccc2)=NC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 2.5 | To a solution of 2.85 g. (0.01 mole) of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine in 100 ml. of tetrahydrofuran under nitrogen is added with stirring, 0.847 ml. (0.012 mole) of pyruvic acid. After 2.5 hours at room temperature and overnight at 0° C. 7-chloro-2-[(1-carboxyethylidene)hydrazino]-5-phenyl-3H-1,4-... | CC(=NNC1=Nc2ccc(Cl)cc2C(c2ccccc2)=NC1)C(=O)O | null | null | null |
698,592 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | [CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14](OS(C)(=O)=O)[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2].[C:22]([O-:25])(=[S:24])[CH3:23].[K+]>CN(C)C=O>[C:22]([S:24][CH:14]1[CH2:13][CH2:12][N:11]([C:8]2[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[CH2:16][CH2:15]1)(=[O:25])[CH3:23] | CC([O-])=S | CCOC(=O)c1csc(N2CCC(OS(C)(=O)=O)CC2)n1 | null | [K+] | 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 | 80 | 8 | To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-4-methanesulfonyloxypiperidine (76 mg, 0.23 mmol) (obtained as described in Reference Example 13(3)) in dimethylformamide (4.0 ml) was added potassium thioacetate (145 mg, 1.3 mmol) at room temperature, and the reaction mixture was then stirred in an oil bath (80° ... | CCOC(=O)c1csc(N2CCC(SC(C)=O)CC2)n1 | null | 92.6 | null |
311,683 | ord_dataset-04982f13ed08448d93df6794846500f3 | null | 1995-01-01T00:06:00 | true | COC1C=C(OC)N=C(O[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[C:19](=O)[O:18][CH:17]3[OH:22])N=1.[CH:23]([Mg]Cl)=[CH2:24].Cl>O1CCCC1>[CH:23]([CH:19]1[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17](=[O:22])[O:18]1)=[CH2:24] | C=C[Mg]Cl | COc1cc(OC)nc(Oc2cccc3c2C(=O)OC3O)n1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | 3.6 g of 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxyphthalide (see Example 84) are placed in 60 ml of absolute tetrahydrofuran at -45° C., and the solution is treated within 10 minutes with 18 ml of a 2M solution of vinylmagnesium chloride solution in tetrahydrofuran. The reaction solution is then stirred for appro... | C=CC1OC(=O)c2ccccc21 | null | null | null |
176,793 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | Br[C:2]1([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]1=[O:14].N12CCCN=C1CCCCC2>O1CCCC1>[OH:14][C:3]1[C:4]2[C:9](=[CH:8][C:7]([O:12][CH3:13])=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:15]([O:17][CH3:18])=[O:16] | COC(=O)C1(Br)CCc2cc(OC)ccc2C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCC2=NCCCN2CC1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 16 | A solution of 10.2 g (0.033 mole) of 1,2,3,4-tetrahydro-2-bromo-6-methoxy-1-oxo-2-naphthalenecarboxylic acid, methyl ester in 100 ml of tetrahydrofuran under a nitrogen atmosphere was treated over 15 minutes with a solution of 10.0 ml (10.2 g; 0.067 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 20 ml of tetrahydrofura... | COC(=O)c1ccc2cc(OC)ccc2c1O | null | 66.5 | null |
635,028 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[NH:15][C:16](=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:16]([NH:15][C:14]1[CH:13]=[C:12]([NH:11][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:21]=[CH:20][CH:19]=1... | O=[N+]([O-])c1cccnc1Cl | CC(=O)Nc1cccc(N)c1 | null | O=C([O-])[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 | null | null | A mixture of 2-chloro-3-nitropyridine (6.12 g), 3′-aminoacetanilide (5.80 g) and potassium carbonate (5.34 g) in toluene (50 ml) was refluxed for 5 hours. The mixture was cooled, and the solids were collected and washed with water, ethanol and isopropyl ether successively to give 2-(3-acetamidophenyl)amino-3-nitropyrid... | CC(=O)Nc1cccc(Nc2ncccc2[N+](=O)[O-])c1 | null | 55.9 | null |
211,797 | ord_dataset-e6e5ffd5405c481d8061087049155f9f | null | 1990-01-01T00:07:00 | true | [N:1]#[N:2].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:15]([NH:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C@@H:12]([CH3:14])[OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>N1C=CC=CC=1>[N:1]#[N:2].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:15]([NH:17][O:18][CH2:19][C:20]1[C... | CS(=O)(=O)Cl | C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)NOCc1ccccc1 | null | Cl | N#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 0 | 2.5 | N2 -(t Butyloxycarbonyl)-N-(Phenylmethoxy)-L-threonineamide (244 g) was dissolved in 1.2 liters of pyridine and the solution was cooled to 0° C. With stirring 120 grams of methanesulfonyl chloride was added dropwise at 0°-5° C. After 2.5 hours, the reaction mixture was poured into a mixture of 1500 ml of 2N hydrochlori... | C[C@@H](OS(C)(=O)=O)[C@H](NC(=O)OC(C)(C)C)C(=O)NOCc1ccccc1 | null | null | null |
1,313,641 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | Cl.[NH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13].C(N(CC)CC)C.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]=[C:38]=[O:39])=[CH:33][CH:32]=1>C1COCC1>[O:21]=[C:15]1[CH:14]([N:7]2[CH2:6][C:5]3[C:9](=[CH:10][CH:11]=[CH:12][... | NCc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O | COc1ccc(N=C=O)cc1 | null | Cl | 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 | 5 | 8 | A stirred suspension of 3-(4-aminomethyl-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione hydrochloride (0.7 g, 2.1 mmol) and triethylamine (0.3 g, 2.7 mmol) in THF (30 mL) was cooled to 5° C. 4-Methoxyphenyl isocyanate (0.4 g, 2.7 mmol) was added, and the mixture was stirred at room temperature overnight. The rea... | COc1ccc(NC(=O)NCc2cccc3c2CN(C2CCC(=O)NC2=O)C3=O)cc1 | null | 90.2 | null |
1,437,245 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [H-].[Na+].[C:3]([O:7][C:8](=[O:23])[NH:9][C:10]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:12][CH:13]=[N:14][CH:15]=1)([CH3:6])([CH3:5])[CH3:4].IC.[C:26](=O)(O)[O-].[Na+]>O1CCCC1>[C:3]([O:7][C:8](=[O:23])[N:9]([CH3:26])[C:10]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:12][CH... | Cc1ccccc1-c1ncncc1NC(=O)OC(C)(C)C | O=C([O-])O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.17 | Sodium hydride (75 mg, 1.87 mmol) was added to a stirring solution of (4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert-butyl ester (410 mmol, 1.44 mmol) in tetrahydrofuran (10 mL) under Argon atmosphere. After 10 min., iodomethane (117 μL, 1.87 mmol) was added. The reaction mixture was stirred for 16 hours and then poured... | Cc1ccccc1-c1ncncc1N(C)C(=O)OC(C)(C)C | null | 56 | null |
1,430,709 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | CO[C:3](=O)[CH2:4][NH:5][C:6](=[O:37])[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:21]([N:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH:33]3[CH2:35][CH2:34]3)[CH2:25][CH2:24]2)=[O:22])=[CH:9][C:8]=1[Cl:36].NCC[CH2:42][S:43]([OH:46])(=[O:45])=[O:44]>>[Cl:36][C:... | NCCCS(=O)(=O)O | COC(=O)CNC(=O)c1cc(Cl)c(Oc2ccncc2C(=O)N2CCN(C3CC3)c3ccccc32)cc1Cl | null | null | null | null | null | null | null | 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 in analogy to Example 35, from 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid (Example 29, intermediate) and 3-amino-1-propanesulfonic acid (commercially available, CAS RN 3687-18-1). Brown solid (18%). MS (ESI): m/z=605.102 [M+H]+. | O=C(NCCCS(=O)(=O)O)c1cc(Cl)c(Oc2ccncc2C(=O)N2CCN(C3CC3)c3ccccc32)cc1Cl | null | null | null |
1,574,627 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]1[NH:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1)[CH3:2].[Br:15]Br>ClCCl>[Br:15][C:5]1[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][NH:8][C:4]=1[O:3][CH2:1][CH3:2] | BrBr | CCOc1cc(-c2ccccc2)n[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 5-ethoxy-3-phenyl-1H-pyrazole (1.0 g, 5.31 mmol) in dichloromethane (20 mL), was added bromine (0.849 g, 5.31 mmol) dropwise at room temperature. The reaction was stirred for 2 h, washed with saturated NaHCO3 solution and concentrated under reduced pressure. The residue was triturated with 10% ethyl ac... | CCOc1[nH]nc(-c2ccccc2)c1Br | null | 84.6 | null |
690,762 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | [C:1]1([C:7]2[C:8](=[O:12])[O:9][CH2:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)(O)[C:15]#[N:16].CN(C)C(=N)N(C)C.Cl>CC#N>[O:12]=[C:8]1[O:9][CH2:10][CH:11]([C:15]#[N:16])[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | CC(C)(O)C#N | O=C1OCC=C1c1ccccc1 | null | CN(C)C(=N)N(C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | -0 | 0.25 | 3-Phenyl-5H-furan-2-one (Description 2; 4.5 g, 0.028 mol), and acetone cyanohydrin (3.06 ml) were dissolved in CH3CN (80 ml) and cooled to −0° C. Tetramethylguanidine (3.5 ml) was added dropwise over 15 minutes and the reaction left to stand for a further 15 minutes. 0.5M HCl (100 ml) was added and the reaction mixture... | N#CC1COC(=O)C1c1ccccc1 | null | 56 | null |
1,230,513 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH3:11])[CH:3]=1.[C:12]1([S:18]([NH2:21])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:21][S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])=[C:4]([O... | NS(=O)(=O)c1ccccc1 | COc1cc(O)ccc1C=O | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | 25 | null | An equimolar mixture of 27.4 g (0.18 mol) 4-hydroxy-2-methoxybenzaldehyde and 28.3 g (0.18 mol) benzenesulfonamide was placed into toluene. 100 mg p-toluenesulfonic acid was added as a catalyst. The mixture was then heated under reflux on a water separator until the theoretically calculated quantity of water had separa... | COc1cc(O)ccc1C=NS(=O)(=O)c1ccccc1 | null | null | null |
654,014 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | C([O:3][C:4](=[O:43])[CH2:5][CH2:6][NH:7][C:8]1[S:9][C:10](=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][CH:24]([NH:27][CH2:28][C@H:29]([OH:42])[CH2:30][O:31][C:32]4[C:40]5[NH:39][C:38](=[O:41])[NH:37][C:36]=5[CH:35]=[CH:34][CH:33]=4)[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[C:11](=[O:13])[N:12]=1)C.[OH-].[Na... | CCOC(=O)CCNC1=NC(=O)C(=Cc2ccc(N3CCC(NC[C@H](O)COc4cccc5[nH]c(=O)[nH]c45)CC3)cc2)S1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 3-[5-(4-{4-[(2S)-2-hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzylidene)-4-oxo-4,5-dihydro-thiazol-2-ylamino]-propionic acid ethyl ester(which was obtained in Example 8)by NaOH hydrolysis as a pale yellowish solid; MS (ES) m/z: 291.0 ((M+2H... | O=C(O)CCNC1=NC(=O)C(=Cc2ccc(N3CCC(NC[C@H](O)COc4cccc5[nH]c(=O)[nH]c45)CC3)cc2)S1 | null | null | null |
550,869 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[OH:17].[CH2:18](I)[CH2:19][CH2:20][CH3:21]>>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[O:17][CH2:18][CH2:19][CH2:20][CH3:21] | CCOC(=O)c1cc2ccccc2c(Br)c1O | CCCCI | null | null | null | null | null | null | null | 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 intermediate was prepared from ethyl 4-bromo-3-hydroxynaphthalen-2-carboxylate and butyl iodide in almost quantitative yield and used for the next step without further purification. | CCCCOc1c(C(=O)OCC)cc2ccccc2c1Br | null | null | null |
1,356,087 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].CC(C)([O-])C.[K+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[O:10])[CH2:20][CH2:19][C:18]... | C=CC(=O)OC | O=C(Cc1cccc(Cl)c1)c1ccc(Cl)cc1 | null | CC(C)(C)[O-] | [K+] | 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 | 1 | To a solution of 52.1 g (197 mmol) of 2-(3-chlorophenyl)-1-(4-chlorophenyl)ethanone (Example 1, Step A) and methyl acrylate (19.5 ml, 216 mmol) in 360 mL of THF was added 20 mL of a 1M solution of potassium tert-butoxide in THF slowly at 0° C. over a period of 20 min (reaction solution temp kept<10° C.). The reaction w... | COC(=O)CCC(C(=O)c1ccc(Cl)cc1)c1cccc(Cl)c1 | null | null | null |
298,812 | ord_dataset-b6309a86b70f4ca08fd301828cacf950 | null | 1994-01-01T00:10:00 | true | [O:1]1[C:19]2=[C:20]3[C@:15]([CH3:22])([CH2:16][CH2:17][C@@H:18]2[OH:21])[C@@H:14]2[C@H:4]([C@H:5]4[C@:11]([CH3:23])([CH2:12][CH2:13]2)[C@@H:8]([CH2:9][CH3:10])[CH2:7][CH2:6]4)[C@@H:3]2[O:24][C@:2]123.N1C=CC=CC=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C(Cl)Cl>[C:31]([O:21][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:22])[C:20]3[C... | CC[C@H]1CC[C@H]2[C@@H]3[C@@H]4O[C@]45OC4=C5[C@](C)(CC[C@@H]4O)[C@H]3CC[C@]12C | CC(=O)OC(C)=O | 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 | 25 | 8 | To a mixture of 0.084 g (0.189 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl )-1α,260 ;6α,7α-diepoxypregn- 4-en-3β-ol, 0.5 ml (6.18 mmoles) of dry pyridine and 5 ml of methylene chloride was gradually added 0.1 ml (1.06 mmoles) of acetic anhydride dropwise at a temperature of 0° C. and the solution was stirred at room tem... | CC[C@H]1CC[C@H]2[C@@H]3[C@@H]4O[C@]45OC4=C5[C@](C)(CC[C@@H]4OC(C)=O)[C@H]3CC[C@]12C | null | 90 | null |
1,448,757 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[Br-].[CH2:17]([Zn+])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2... | Cc1c(Cl)nc2cc(F)cc(F)c2c1Cl | [Zn+]CCc1ccccc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 60 | 2 | A screw cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (500 mg, 2.016 mmol), tetrakis(triphenylphosphine)palladium(0) (233 mg, 0.202 mmol), and THF (5.04 mL). The mixture was sparged with N2, then phenethyl-zinc(II) bromide (0.5 M in THF, 4.23 mL, 2.116 mmol) was added and the reaction stirred at... | Cc1c(CCc2ccccc2)nc2cc(F)cc(F)c2c1Cl | null | null | null |
1,465,540 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][OH:29])[CH:23]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:33]>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:1... | CI | CC(C)(C)OC(=O)N1CCC(CCN2CCN(c3cccc(CO)c3)CC2)CC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A solution of 0.4 g (1 mmol) of 4-{2-[4-(3-hydroxymethylphenyl)piperazin-1-yl]ethyl}piperidine-1-carboxylic acid tert-butyl ester in 10 mL of dry dimethyl sulfoxyde is cooled at a temperature close to 5° C. and 40 mg (1 mmol) of sodium hydride (60% suspension) is added. The mixture is stirred for 30 minutes at room tem... | COCc1cccc(N2CCN(CCC3CCN(C(=O)OC(C)(C)C)CC3)CC2)c1 | null | 71.8 | null |
1,587,105 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [CH:1]1([C@@H:4]2[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][C@H:5]2[C:16](OCC)=[O:17])[CH2:3][CH2:2]1.[Li+].[BH4-]>C1COCC1>[CH:1]1([C@H:4]2[C@H:5]([CH2:16][OH:17])[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]2)[CH2:2][CH2:3]1 | CCOC(=O)[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]1C1CC1 | null | null | [BH4-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1-tert-butyl 3-ethyl(trans)-4-cyclopropylpyrrolidine-1,3-dicarboxylate (9.2 g, 13 mmol) and LiBH4 (1.37 g, 65 mmol) in dry THF (75 mL) was refluxed overnight. TLC (petroleum ether:EtOAc 5:1) indicated the reaction was complete. The reaction mixture was quenched by addition of water (75 mL) and extracted wi... | CC(C)(C)OC(=O)N1C[C@@H](CO)[C@H](C2CC2)C1 | null | 76.5 | null |
12,563 | ord_dataset-a0071d97083e4e69ae8872417ed2776b | null | 1976-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[C:8]2[CH2:9][C:10]3[C:15]([C:16]4([CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.[N:23]#CBr>C(Cl)Cl>[C:22]([N:19]1[CH2:20][CH2:21][C:16]2([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[CH2:9][C:10]3[C:15]2=[CH:14][CH:13]=[CH:12][C... | N#CBr | COc1cccc2c1Cc1ccccc1C21CCN(C)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | 4-Methoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine (12.6 g.) and cyanogen bromide (5.6 g.) in methylene chloride (250 ml.) are stirred at room temperature for 18 hours. The reaction mixture is evaporated to dryness, and the residue is taken up in chloroform, the solution washed with water and with brine, ... | COc1cccc2c1Cc1ccccc1C21CCN(C#N)CC1 | null | null | null |
919,314 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [CH3:1][S:2][C:3]1[CH:4]=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1.[CH:11](O)=O.C([O-])(O)=O.[Na+]>Cl>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]=[CH:11][NH:10][C:5]=2[CH:4]=1 | CSc1ccc(N)c(N)c1 | O=CO | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | 4-(Methylthio)benzene-1,2-diamine (10.7 g, 69.2 mmol) was dissolved in 230 mL of aqueous 4N HCl with stirring. Formic acid (7.85 mL, 208 mmol) was added and the reaction was refluxed for 1 h. The reaction was cooled to rt then concentrated in vacuo to a dark solid. The dark solid was dissolved In 500 mL of MeOH with st... | CSc1ccc2nc[nH]c2c1 | null | 99.4 | null |
1,023,346 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:11]([CH2:23][CH3:24])[C:12]3[C:17]([C:18]=2[C:19]#[N:20])=[CH:16][CH:15]=[C:14]([O:21][CH3:22])[CH:13]=3)=[CH:4][CH:3]=1.[Cl:25][CH2:26][CH2:27][N:28]=[C:29]=[O:30]>C1(C)C=CC=CC=1.CC(C)=O>[Cl:25][CH2:26][CH2:27][NH:28][C:29]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9]... | O=C=NCCCl | CCn1c(C#Cc2ccc(N)cc2)c(C#N)c2ccc(OC)cc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CC(C)=O | null | null | null | null | null | null | null | null | null | 100 | null | 2-(4-Aminophenylethynyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.32 mmol), prepared as described in Example 1H, is suspended in toluene (600 μL). 2-Chloroethyl isocyanate (32 μL, 0.37 mmol) is added, and the mixture is heated at 100° C. for 5 h. The reaction mixture is then cooled, diluted in acetone, and... | CCn1c(C#Cc2ccc(NC(=O)NCCCl)cc2)c(C#N)c2ccc(OC)cc21 | null | 54.2 | null |
1,513,950 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | F[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH:15]=[CH2:16])[CH:3]=1.[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18]>N1C=CC=CC=1>[C:17]([NH:21][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH:15]=[CH2:16])[CH:3]=1)([CH3:20])([CH3:19])[CH3:18] | C=Cc1cc(F)c([N+](=O)[O-])cc1C(=O)OC | CC(C)(C)N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a mixture of 10.45 g of methyl 4-fluoro-5-nitro-2-vinylbenzoate and 104.5 mL of pyridine was added 14.69 mL of tert-butylamine, followed by stirring at room temperature overnight. The solvent was evaporated under reduced pressure, and to the residue were added water and ethyl acetate, followed by extraction with eth... | C=Cc1cc(NC(C)(C)C)c([N+](=O)[O-])cc1C(=O)OC | null | null | null |
468,594 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([C:17]([O-:19])=O)=[C:10]([C:14]([O-])=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[NH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][CH:25]=1.Cl>>[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:6][C:7]2=[CH:8][C:9]3[C:17... | NC(=O)c1ccc(N)cc1 | CCCN(CCC)C1Cc2cc(C(=O)[O-])c(C(=O)[O-])cc2C1 | 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 | Using procedure 49, 2-(dipropylamino)-2,3-dihydro-1H-indene-5,6-dicarboxylate (92, 0.3 g, 1.0 mmol) was treated with 4-aminobenzamide (1.4 g, 10.0 mmol). Purification on silica gel, eluting with 9:1 CH2Cl2 /MeOH sat'd w/ NH3, afforded a solid that was converted to an HCl salt and recrystallized from EtOAc/MeOH to give ... | CCCN(CCC)C1Cc2cc3c(cc2C1)C(=O)N(c1ccc(C(N)=O)cc1)C3=O | null | null | null |
1,554,018 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Cl[C:2]1C=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.C=C1CC[N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])CC1>C(Cl)Cl>[C:22]([O:21][C:19]([N:16]1[CH2:2][CH2:3][C:4]2([O:10][CH2:8]2)[CH2:5][CH2:6]1)=[O:20])([CH3:25])([CH3:24])[CH3:23] | O=C(OO)c1cccc(Cl)c1 | C=C1CCN(C(=O)OC(C)(C)C)CC1 | 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 | 15 | m-Chloroperbenzoic acid (1.14 g, 6.6 mmol) was added to a solution of tert-butyl 4-methylenepiperidine-1-carboxylate (1 g, 5.1 mmol) in CH2Cl2 (30 mL) at 0° C. The reaction mixture was stirred for 15 h at rt, diluted with CH2Cl2, washed with a saturated aqueous solution of NaHCO3 and brine, dried (Na2SO4), and evaporat... | CC(C)(C)OC(=O)N1CCC2(CC1)CO2 | null | 101.1 | null |
1,735,112 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=[CH:2]1.N=C=N.C1C=CC2N(O)N=NC=2C=1.[NH2:22][C@H:23]([C:33]1[NH:34][C:35]([C:38]2[C:39]([O:48][CH3:49])=[N:40][C:41]3[C:46]([CH:47]=2)=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:36][N:37]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:31][CH3:32])=[O:30].C(O)C(N)(CO)CO>C(Cl)Cl.CN... | O=C(O)c1cncs1 | CNC(=O)CCCCC[C@H](N)c1ncc(-c2cc3ccccc3nc2OC)[nH]1 | null | N=C=N | NC(CO)(CO)CO | On1nnc2ccccc21 | 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 | 0.17 | A glass tube was charged with thiazole-5-carboxylic acid (1.5 eq.), PS-carbodiimide resin (2 eq.), HOBt (1.7 eq.) and diluted with DCM (0.04 M). The tube was capped and stirred on a rotor for 10 min. Then, a solution of A4 in DMF (0.06 M) was added and the reaction mixture was stirred in a rotor for 24 h. After additio... | CNC(=O)CCCCC[C@H](NC(=O)c1cncs1)c1ncc(-c2cc3ccccc3nc2OC)[nH]1 | null | null | null |
594,425 | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | null | 2003-01-01T00:05:00 | true | Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.[F-].[K+]>C1COCC1>[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | Brc1ccccc1 | Cc1ccccc1B(O)O | null | [F-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 2-Bromobenzene (80 mg, 0.51 mmol) reacted with 2-methylphenylboronic acid (90 mg, 0.66 mmol) using 1.0 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.55 mmol) in THF solvent at room temperature to give the title compound (80 mg, 95%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.51-7.47 (m, 2H), 7.44-7.40 (m, 3H),... | Cc1ccccc1-c1ccccc1 | null | 93.2 | null |
1,420,549 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | CC([N:5]([C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[C:23]([F:29])[CH:22]=3)[N:18]=[C:17]([NH:30][CH3:31])[N:16]=2)[CH2:10]1)C(=O)[O-])(C)C.[ClH:32].O1CCOCC1>>[ClH:32].[NH2:5][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]=[C:17]([NH:30][CH3:31])[N:18... | CNc1nc(-c2ccc(C#N)c(F)c2)cc(N2CCC[C@@H](N(C(=O)[O-])C(C)(C)C)C2)n1 | null | null | Cl | null | null | 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 | To 1,1-dimethylethyl{(3R)-1-[6-(4-cyano-3-fluorophenyl)-2-(methylamino)-4-pyrimidinyl]-3-piperidinyl}carbamate (0.544 g, 1.28 mmol) was added HCl in dioxane (4 mL, 16.00 mmol) at room temperature with stirring. A precipitate immediately formed. The mixture was stirred at room temperature overnight, and then concentrate... | CNc1nc(-c2ccc(C#N)c(F)c2)cc(N2CCC[C@@H](N)C2)n1 | null | null | null |
1,069,301 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][CH:30]4[CH2:32][CH2:31]4)=[O:28])=[C:22]([CH3:33])[C:21]=3[CH3:34])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:35]#[N:36])C1C=CC=CC=1>[C].[Pd].O1CCCC1>[CH3:33][C:22]1[C:21]([CH3:34])=[C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:... | Cc1c(NC(=O)NC2CC2)ccc(Oc2ccnc3cc(OCc4ccccc4)c(C#N)cc23)c1C | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | After adding N-[4-(7-benzyloxy-6-cyanoquinolin-4-yloxy)-2,3-dimethylphenyl]-N′-cyclopropylurea (1600 mg) to tetrahydrofuran (400 ml), palladium-carbon (2000 mg) was further added and the mixture was stirred overnight at room temperature under a hydrogen atmosphere. The palladium-carbon was removed by filtration, washin... | Cc1c(NC(=O)NC2CC2)ccc(Oc2ccnc3cc(O)c(C#N)cc23)c1C | null | 63.7 | null |
440,172 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[N:21]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:22][CH2:23][CH2:24][C:25](OCC)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:... | CCOC(=O)CCCN(C1CC(C)(C)Oc2ccc(OCc3ccccc3)cc21)S(C)(=O)=O | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 5.7 g (12 mmol) of ethyl 4-[(6-benzyloxy-2,2-dimethylchroman-4-yl)-methanesulfonylamino]-N-butyrate (Ex. 28f) were treated with 10 ml of 1 M lithium aluminum hydride solution in THF in 100 ml of THF at 0° C. The mixture was treated at RT with a little water, then with 1N hydrochloric acid, and concentrated, and the res... | CC1(C)CC(N(CCCCO)S(C)(=O)=O)c2cc(OCc3ccccc3)ccc2O1 | null | null | null |
1,315,815 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:16])=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:17][N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:16][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:21]3[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=3)[... | Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1 | Cc1cc(N)ncc1Oc1ccnc(Cl)c1 | null | O=C([O-])[O-] | [Cs+] | 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 | 90 | null | 5-(2-chloropyridin-4-yloxy)-4-methylpyridin-2-amine (0.116 g, 0.492 mmol) was dissolved in DMF (2 ml) and 1-methyl-1H-pyrazole-4-boronic acid pinacol ester (0.154 g, 0.738 mmol) was added, followed by cesium carbonate (0.481 g, 1.477 mmol) and water (0.667 ml). Argon was bubbled through the mixture for several minutes,... | Cc1cc(N)ncc1Oc1ccnc(-c2cnn(C)c2)c1 | null | 60.7 | null |
516,708 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | O[N:2]=[C:3]([C:11](=O)[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>C(#N)C>[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]2[NH:25][C:11]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[C:3]([C:4]([O:6]... | CC(C)(C)OC(=O)C(=NO)C(=O)c1ccncc1 | Cc1ccc(CN)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | tert-Butyl 2-hydroxyimino-3-oxo-3-(4-pyridyl)propionate and 4-methylbenzylamine were dissolved in acetonitrile (80 ml). The mixture was reacted and treated in the same manner as in Starting Material Synthetic Example 5 to give tert-butyl 2-(4-methylphenyl)-5-(4-pyridyl)imidazole-4-carboxylate. | Cc1ccc(-c2nc(C(=O)OC(C)(C)C)c(-c3ccncc3)[nH]2)cc1 | null | null | null |
606,721 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2/[C:17](=[N:19]/[OH:20])/[NH2:18])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:21][N:22]([CH3:28])[CH2:23][CH2:24][C:25](O)=[O:26].CN1CCOCC1.O.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>>[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2... | N/C(=N\O)[C@@H]1CCCCN1S(=O)(=O)CC1CCCCC1 | CN(C)CCC(=O)O | null | CCN=C=NCCCN(C)C | Cl | Oc1cccc2[nH]nnc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCOCC1 | O | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by the method of Preparation 5 from (Z)-(2S)-1-[cyclohexylmethylsulfonyl]-N′2-hydroxy-2-piperidinecarboximidamide [see Preparation 28], 3-(dimethylamino)propanoic acid [Papapoulos, et al, WO 9619998A1], N-methyl morpholine, hydroxybenzotriazole hydrate and 1-(3-dimethylaminopropyl)-3-eth... | CN(C)CCC(=O)O/N=C(\N)[C@@H]1CCCCN1S(=O)(=O)CC1CCCCC1 | null | null | null |
201,320 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[N:10]([N:13]=[CH:14][N:15]=2)[C:11]=1O)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:11]1[N:10]2[N:13]=[CH:14][N:15]=[C:9]2[N:8]=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5] | O=P(Cl)(Cl)Cl | CCOC(=O)c1cnc2ncnn2c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A suspension of 6-ethoxycarbonyl-7-hydroxy-s-triazolo [1,5-a]pyrimidine (7 g) in phosphorus oxychloride (20 ml) was refluxed for 30 minutes, the resultant orange solution was further refluxed for one hour, and excess phosphorus oxychloride was removed by distillation under reduced pressure. Benzene (50 ml) was added to... | CCOC(=O)c1cnc2ncnn2c1Cl | null | null | null |
251,899 | ord_dataset-49bd993346b64eeeb2a8fe2643164a0a | null | 1992-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[O:8][CH2:7]1.[NH2:14][CH2:15][CH2:16][C:17]1[NH:18][C:19]2[CH:25]=[C:24]([C:26]3[CH2:27][CH2:28][C:29](=[O:32])[NH:30][N:31]=3)[CH:23]=[CH:22][C:20]=2[N:21]=1>>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[O:4][CH2:5][CH:6]([OH:8])... | Cc1ccc(Cl)c(OCC2CO2)c1 | NCCc1nc2ccc(C3=NNC(=O)CC3)cc2[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 1 from 1-(2-chloro-5-methyl-phenoxy)-2,3-epoxypropane and 6-[2-(2-aminoethyl)benzimidazol-5-yl]-4,5-dihydro-3(2H)-pyridazinone. | Cc1ccc(Cl)c(OCC(O)CNCCc2nc3ccc(C4=NNC(=O)CC4)cc3[nH]2)c1 | null | null | null |
1,445,646 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([C:3]1[C:4]([CH:19]([C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=2)[CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)=[C:5]([C:14](OCC)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].NN>C(O)C.C(Cl)Cl>[N:8]1([C:7]2[S:6][C:5]3[C:14](=[O:15])[NH:21][CH2:20][CH:19]([C:32]4[... | CCOC(=O)c1sc(N2CCOCC2)c(C#N)c1C(CN1C(=O)c2ccccc2C1=O)c1ccc2ccccc2c1 | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCO | null | null | null | null | null | null | null | null | null | 25 | 40 | To a solution of ethyl 4-cyano-3-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-(2-naphthyl)ethyl]-5-(morpholin-4-yl)thiophene-2-carboxylate (0.126 g, 0.223 mmol) in ethanol (4.0 mL) and methylene chloride (1.0 mL) was added hydrazine (23.3 mg, 0.727 mmol). After 40 h of stirring at rt, hydrazine (25 mg, 0.78 mmol) was ... | N#Cc1c(N2CCOCC2)sc2c1C(c1ccc3ccccc3c1)CNC2=O | null | 77.4 | null |
1,502,027 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].FC(F)(F)C(O)=O.[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[NH:27][C:28]3[CH:29]=[N:30][CH:31]=[C:32]([CH:53]=3)[CH2:33][CH2:34][C:35]3[CH:43]=[C:39]([NH:40][C:41]=1[N:42]=2)[CH:38]=[CH:37][C:36]=3[NH:44][C:45](=[O:52])[CH2:46][C@@H:47]... | Cn1cc(C(=O)Cl)cn1 | O=C(C[C@@H]1CCNC1)Nc1ccc2cc1CCc1cncc(c1)Nc1ncc(Cl)c(n1)N2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | The desired compound was prepared according to the procedure of Example D94 using N-[6-chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]-2-[(3S)-pyrrolidin-3-yl]acetamide tris(trifluoroacetate) and 1-methyl-1H-pyrazole-4-carbonyl chloride as the starting ... | Cn1cc(C(=O)N2CC[C@@H](CC(=O)Nc3ccc4cc3CCc3cncc(c3)Nc3ncc(Cl)c(n3)N4)C2)cn1 | null | 72 | null |
597,728 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | [OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2[N+:19]([O-])=O)[CH2:4][CH2:3]1>[Pd].CO.O1CCOCC1>[NH2:19][C:10]1[CH:11]=[C:12]([C:15]([F:16])([F:17])[F:18])[CH:13]=[CH:14][C:9]=1[NH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]1 | O=[N+]([O-])c1cc(C(F)(F)F)ccc1N[C@H]1CC[C@H](O)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | 25 | 4 | A mixture of 4-(trans-4-hydroxycyclohexylamino)-3-nitrobenzotrifluoride (4.0 g) and 10% palladium on activated carbon (400 mg) in a mixture of methanol (20 mL) and dioxane(20 mL) was stirred under hydrogen atmosphere (3 atm) at ambient temperature for 4 hours. The reaction mixture was filtered through a celite pad, and... | Nc1cc(C(F)(F)F)ccc1N[C@H]1CC[C@H](O)CC1 | null | null | null |
1,350,163 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | COC1C=CC(C[N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[C:17]2[C:18]([NH:23][C:24]3[C:25]([CH3:43])=[CH:26][CH:27]=[C:28]4[C:33]=3[N:32]=[CH:31][N:30]=[C:29]4[NH:34][C:35]3[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)=CC=1>C(O)(C(F)(F)F)=O>[N:12]1[C:13]([C:17]2[... | COc1ccc(Cn2cnc3c(-c4cccnc4Nc4c(C)ccc5c(Nc6ccc(C#N)cc6)ncnc45)ncnc32)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 70 | 0.08 | A mixture of 4-(8-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile (91 mg, 154 μmol) in TFA (3 mL) was heated at 70° C. for 3 h. The TFA was removed in vacuo and 2M NH3/MeOH was added. The mixture was stirred for 5 min and solvent was removed in vacuo. The product was p... | Cc1ccc2c(Nc3ccc(C#N)cc3)ncnc2c1Nc1ncccc1-c1ncnc2[nH]cnc12 | null | null | null |
407,102 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | C1(O[C:8](=[O:19])[NH:9][C:10]2[CH:11]=[N:12][C:13]([CH3:18])=[C:14]([CH2:16][CH3:17])[CH:15]=2)C=CC=CC=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[CH2:16]([C:14]1[CH:15]=[C:10]([NH:9][C:8]([N:31]2[CH2:30][CH2:29][N:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH... | CCc1cc(NC(=O)Oc2ccccc2)cnc1C | COc1ccccc1N1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Phenyl-N-(5-ethyl-6-methylpyridin-3-yl)carbamate and 1-(2-methoxyphenyl)piperazine were reacted by the same way with the example 1 to obtain the titled compound. | CCc1cc(NC(=O)N2CCN(c3ccccc3OC)CC2)cnc1C | null | 80 | null |
311,307 | ord_dataset-04982f13ed08448d93df6794846500f3 | null | 1995-01-01T00:06:00 | true | [C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.O>CN(C)C=O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6] | O=C1NC(=O)c2ccccc21 | BrCCCCCBr | null | [K] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 2 | Potassium phthalimide (5.4 mmoles) was added to a solution of 1,5-dibromopentane (3.72 g; 16.2 mmoles) in dimethylformamide (8 ml) and heated to 80° C. approx. under stirring. After 2 hours, water was added and the solution was repeatedly extracted with ether. The collected organic phases were washed with water, dried ... | O=C1NC(=O)c2c(CCCCCBr)cccc21 | null | 281.4 | null |
1,490,345 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C[C:2]12[CH2:11][C:9]3([NH2:12])[CH2:10][CH:4]([CH2:5][C:6](C)([CH2:8]3)[CH2:7]1)[CH2:3]2.Cl.Cl>>[C:9]12([NH2:12])[CH2:10][CH:4]3[CH2:3][CH:2]([CH2:7][CH:6]([CH2:5]3)[CH2:8]1)[CH2:11]2 | CC12CC3CC(C)(C1)CC(N)(C3)C2 | null | 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 | In a manner similar to the preparation of the compound of formula DC in Example 13, the compound of formula SA was prepared except that the compound of formula EC was used in place of the compound of formula DB and memantine hydrochloride (i.e., the hydrochloride of 1-amine-3,5-dimethyl-adamantane, Sigma-Aldrich) was u... | NC12CC3CC(CC(C3)C1)C2 | null | 5 | null |
323,052 | ord_dataset-24ad29d930104afea313b6c3bd11099e | null | 1996-01-01T00:01:00 | true | O.[C:2]1([C:8]([CH:10]=[O:11])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]1([CH3:19])[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1>ClC(Cl)C.[Ti](Cl)(Cl)(Cl)Cl>[CH3:19][C:12]1[CH:17]=[C:16]([CH:15]=[C:14]([CH3:18])[CH:13]=1)[CH:10]([OH:11])[C:8](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | Cc1cccc(C)c1 | O=CC(=O)c1ccccc1 | null | Cl[Ti](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | Phenylglyoxal monohydrate (304 mg, 2 mM) and m-xylene (0.49 ml, 4 mM) were dissolved in dichloroethane (4 ml), titanium tetrachloride (0.33 ml, 3 mM) was added, and reacted at room temperature for 30 minutes. Using the same procedure as in Example 1, 3', 5'-dimethylbenzoin was obtained as a light-yellow oil (363.2 mg, ... | Cc1cc(C)cc(C(O)C(=O)c2ccccc2)c1 | null | null | null |
280,878 | ord_dataset-1953a9402dda47b6bcfe3e3cb9ab8a07 | null | 1993-01-01T00:12:00 | true | [O:1]=[C:2]1[C:12]2[CH:13]=[C:14]([O:17][CH2:18][C:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:11]=2[O:10][C:4]2([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:3]1.[OH-].[Na+].Cl>C(O)C>[O:1]=[C:2]1[C:12]2[CH:13]=[C:14]([O:17][CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:16][C:11]=2[O:10][C:4]2([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[C... | O=C([O-])COc1ccc2c(c1)C(=O)CC1(CCCCC1)O2 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of ethyl (2-{(3,4-dihydro-4-oxospiro [2H-1-benzopyran-2,1'-cyclohexan]-6-yl)oxy}acetate (prepared in Preparation 27) (0.5 g, 1.57 mmol) and 1N sodium hydroxide (1.9 ml, 1.9 mmol), and ethanol (5 ml) is stirred at room temperature for one hour. The mixture is made acid with 1N HCl, filtered, and washed with sm... | O=C(O)COc1ccc2c(c1)C(=O)CC1(CCCCC1)O2 | null | 85.6 | null |
199,818 | ord_dataset-aa9e93ade540499c920a9c3b18e8edaa | null | 1989-01-01T00:11:00 | true | [C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].CN(C)C=O.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[CH2:20]C(O)=O>C1(C)C=CC=CC=1>[Cl:6][CH2:1][C:2](=[O:3])[CH2:20][C:14]1[C:13]([Cl:12])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:19] | O=C(Cl)C(=O)Cl | O=C(O)Cc1c(Cl)cccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2.5 | 50 ml of oxalyl chloride and 0.5 ml of dimethylformamide were added to a stirred suspension of 5.12 g of (2,6-dichlorophenyl)acetic acid in 120 ml of toluene. The mixture was stirred at room temperature for 2.5 hours and then evaporated to dryness. The residue was suspended in 40 ml of diethyl ether and the suspension ... | O=C(CCl)Cc1c(Cl)cccc1Cl | null | null | null |
951,063 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[S:15][C:8]=2[C:7]=1[OH:20])=[O:5])[CH3:2].[CH3:21][Sn](C)(C)C>CN(C=O)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH3:21... | C[Sn](C)(C)C | CCOC(=O)c1nc(Br)c2nc(C(C)(C)C)sc2c1O | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-bromo-2-tert-butyl-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (145 mg, 0.40 mmol), tetramethyl tin (220 μL, 1.6 mmol), dichlorobis(triphenylphosphine)-palladium II (30 mg, 0.04 mmol) in 2.5 mL anhydrous DMF was heated to 130° C. for 1 h. The reaction mixture was cooled, diluted with... | CCOC(=O)c1nc(C)c2nc(C(C)(C)C)sc2c1O | null | 89.2 | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.