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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,444,869 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]=[C:7]([NH:9][C:10]3[N:14]([CH3:15])[C:13]4[CH:16]=[CH:17][C:18]([C:20]([OH:22])=O)=[CH:19][C:12]=4[N:11]=3)[S:8][C:4]=2[CH:3]=1.[N:25]1([CH2:31][CH2:32][OH:33])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>... | Cn1c(Nc2nc3ccc(Cl)cc3s2)nc2cc(C(=O)O)ccc21 | OCCN1CCNCC1 | null | CN(C)C(On1nnc2ccccc21)=[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 | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | [2-(6-Chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazol-5-yl]-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-methanone (315 mg) was prepared by following General Procedure F starting 2-(6-chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid (358 mg), 2-piperazin-1-yl-ethanol (143 mg), HBTU (419 mg),... | Cn1c(Nc2nc3ccc(Cl)cc3s2)nc2cc(C(=O)N3CCN(CCO)CC3)ccc21 | null | 67 | null |
842,079 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [C:1](O)(=O)[CH3:2].Cl.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>CO>[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[C:8]([C:1]3[CH:2]=[CH:15][CH:16]=[CH:17][N:20]=3)=[CH:7][CH:6]=[N:21]2)=[CH:18][CH:19]=1)[C:7]1[CH:8]=[... | CC(=O)O | NNc1ccc(OCc2ccccc2)cc1 | null | Cl | O=C([O-])O | [Na+] | 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 | 60 | null | To a solution of 3-Dimethylamino-1-pyridin-4-yl-propenone (590 mg) in methanol (10 ml) was added acetic acid (0.5 ml) and (4-Benzyloxy-phenyl)-hydrazine hydrogen chloride (836 mg) and the reaction mixture heated to 60° C. for 6 h. The reaction mixture was poured into saturated sodium bicarbonate, extracted with ethyl a... | c1ccc(COc2ccc(-n3nccc3-c3ccccn3)cc2)cc1 | null | null | null |
958,459 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1.[Zn].[Cu]Cl>[CH2:18]([O:17][C:15](=[O:16])[CH:14]=[C:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1)[CH3:19] | CCOC(=O)CBr | COc1ccc2c(c1)CCC2=O | null | Cl[Cu] | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 5-methoxyindanone (150 g, 0.91 mol) in anhydrous tetrahydrofuran (4.5 L), was added zinc (30 mesh, 103.64 g, 1.59 mol) and copper(I) chloride (4.53 g, 0.045 mol). The suspension was stirred under argon atmosphere and refluxed for 15 min; approximately a 25% portion of ethyl bromoacetate (133 mL, 1.18 m... | CCOC(=O)C=C1CCc2cc(OC)ccc21 | null | null | null |
187,006 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | [NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:6][C:7]([CH3:22])([CH2:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17](F)=[CH:16][CH:15]=1)[C:8]([O:10][CH3:11])=[O:9].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:6][C:7]([CH3:22])([CH2:12][C:13](=[O:21])[C:14]1[CH:15]=[CH:16][C:17]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:18][CH:19]=1)[C:... | c1c[nH]cn1 | COC(=O)C(C)(C)CC(=O)c1ccc(F)cc1 | null | O=C([O-])[O-] | [K+] | 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 | null | Imidazole (0.70 g, 0.013 mol) and methyl α,α-dimethyl-4-fluoro-γ-oxobenzene butanoate (2.85 g, 0.012 mol) are dissolved in dimethyl sulfoxide (12.0 ml) in which freshly pulverized potassium carbonate (5.80 g, 0.042 mol) is suspended. The resulting mixture is stirred and heated at 100°-110° for 12 hours. The mixture is ... | COC(=O)C(C)(C)CC(=O)c1ccc(-n2ccnc2)cc1 | null | 62.3 | null |
1,187,932 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [F:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[N:21](S(C3C=CC=CC=3)(=O)=O)[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=2)=[CH:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[NH:21][C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=2)=[CH:9][CH:10]([CH3:12... | CC(C)C=C(c1cccc(F)c1)c1cc2cccnc2n1S(=O)(=O)c1ccccc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCO | null | null | null | null | null | null | null | null | null | 80 | 16 | A solution of 2-(1-(3-fluoro-phenyl)-3-methyl-but-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (2.6 g, 6.2 mmol) in ethanol (8 mL) and tetrahydrofuran (15 mL) was treated with an aqueous sodium hydroxide solution (10%, 20 mL). The reaction was stirred at 80° C. for 16 h. At this time, the reaction mixture was c... | CC(C)C=C(c1cccc(F)c1)c1cc2cccnc2[nH]1 | null | 69 | null |
754,477 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18](O)([C:27]4[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=4)[C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)[CH:16]=3)[N:11]([CH3:34])[C:10](=[O:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:38])=O>>[Cl:38][C:18]([C:15]1[CH:16]=[C:17]2[C:12](=... | O=S(Cl)Cl | Cn1cncc1C(O)(c1ccc(C#N)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)cc(=O)n2C | null | null | null | null | null | 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 | 2 | A mixture of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5yl)methyl]benzonitrile (0.00121 mol), obtained in stage b), in thionyl chloride (6 ml) was stirred at room temperature for 2 hours. The solvent was evaporated. The residue was taken up in DCM. The solvent was e... | Cn1cncc1C(Cl)(c1ccc(C#N)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)cc(=O)n2C | null | null | null |
1,124,957 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [H-].[Na+].[CH3:3][O:4][N:5]([CH3:30])[C:6]([C:8]1[C:13]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=2)(=[O:17])=[O:16])=[CH:12][C:11]([Cl:29])=[CH:10][N:9]=1)=[O:7].[CH3:31][O:32][CH2:33]Cl>C1COCC1>[CH3:3][O:4][N:5]([CH3:30])[C:6]([C:8]1[C:13]([N:14]([CH2:31][O:32][... | COCCl | CON(C)C(=O)c1ncc(Cl)cc1NS(=O)(=O)c1ccc(C)c(C(F)(F)F)c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a mixture of sodium hydride (164 mg, 4.10 mmol) in 5 mL of THF was added a mixture of 5-chloro-3-(4-methyl-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid methoxy-methyl-amide (1.50 g, 3.42 mmol) and chloromethyl methyl ether (0.388 mL, 5.13 mmol) in 5 mL of THF. The mixture was stirred at room te... | COCN(c1cc(Cl)cnc1C(=O)N(C)OC)S(=O)(=O)c1ccc(C)c(C(F)(F)F)c1 | null | 91 | null |
391,924 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | [C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([NH2:11])=[O:10])(=[O:4])[CH:2]=[CH2:3].[C:15](Cl)(=O)C=CC>>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([NH2:11])=[O:10])(=[O:4])[CH:2]=[CH:3][CH3:15] | CC=CC(=O)Cl | C=CC(=O)Nc1cccc(C(N)=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This was achieved by the same procedure as that used to make 3-propenoylaminobenzamide, namely the route of Example 4, except that 2.30 gm (20 mMole) of butenoyl chloride was used. The product obtained had a melting point of 211° C. to 212° C. | CC=CC(=O)Nc1cccc(C(N)=O)c1 | null | null | null |
1,595,337 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([CH:10]([CH3:15])[C:11](OC)=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].CC(C[AlH]CC(C)C)C>C1COCC1>[F:9][C:8]1[CH:7]=[CH:6][C:5]([CH:10]([CH3:15])[CH:11]=[O:12])=[CH:4][C:3]=1[C:1]#[N:2] | COC(=O)C(C)c1ccc(F)c(C#N)c1 | null | null | CC(C)C[AlH]CC(C)C | 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 | 1.5 | A solution of compound methyl 2-(3-cyano-4-fluorophenyl)propanoate (50 mg, 0.24 mmol) in 5 mL of anhydrous THF was cooled to 0° C. and then added DIBAL-H (0.3 mmol) was added. The mixture was warmed to ambient temperature and stirred at ambient temperature for 1.5 hours. The reaction was quenched with water, extracte w... | CC(C=O)c1ccc(F)c(C#N)c1 | null | null | null |
1,746,126 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1Br.[OH:29][C:30]1[CH:31]=[C:32]([NH:36][C:37](=[O:53])[C:38]2[CH:43]=[CH:42][CH:41]=[C:40](B3OC(C)(C)C(C)(C)O3)[CH:39]=2)[... | CC1(C)OB(c2cccc(C(=O)Nc3cccc(O)c3)c2)OC1(C)C | Cc1ccn2nc([C@H](C)Nc3ncnc(N)c3Br)n(-c3ccccc3)c(=O)c12 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | COCCOC | null | null | null | null | null | null | null | null | null | null | null | (S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (55 mg, 0.12 mmol) was treated with N-(3-hydroxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (106 mg, 0.31 mmol, prepared from 3-bromo-N-(3-hydroxyphenyl)benzamide and bis(pinacolato)diboron... | Cc1ccn2nc([C@H](C)Nc3ncnc(N)c3-c3cccc(C(=O)Nc4cccc(O)c4)c3)n(-c3ccccc3)c(=O)c12 | null | 16 | null |
1,294,259 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](N1C=CN=C1)=[O:11])[CH2:2]2.[F:17][C:18]1[CH:19]=[C:20]([CH:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[OH:26])[CH:21]=[C:22]([F:24])[CH:23]=1>>[F:17][C:18]1[CH:19]=[C:20]([CH:25]([O:26][C:10](=[O:11])[O:9][C@@H:3]2[CH:4]3[CH2:5][CH2:6][N:1]... | O=C(O[C@H]1CN2CCC1CC2)n1ccnc1 | OC(c1cccc(F)c1)c1cc(F)cc(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The desired product was prepared by reacting imidazole-1-carboxylic acid (R)-1-aza-bicyclo[2.2.2]oct-3-yl ester with (3,5-difluoro-phenyl)-(3-fluoro-phenyl)-methanol. 1H NMR analysis (300 MHz, DMSO-d6) | O=C(OC(c1cccc(F)c1)c1cc(F)cc(F)c1)O[C@H]1CN2CCC1CC2 | null | null | null |
1,699,483 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[SH:11][CH2:12][CH2:13][OH:14]>>[Cl:1][C:2]1[CH:9]=[C:8]([S:11][CH2:12][CH2:13][OH:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5] | OCCS | N#Cc1ccc(F)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 | 4 g of 2-chloro-4-fluorobenzonitrile was used in Procedure Q with 2-mercaptoethanol to afford 2-chloro-4-(2-hydroxyethylthio)benzonitrile. 1 g of 2-chloro-4-(2-hydroxyethylthio)benzonitrile was reacted via Procedure T to give 2-chloro-4-(2-hydroxyethylthio)benzoic acid. 1 g of 2-chloro-4-(2-hydroxyethylthio)benzoic aci... | N#Cc1ccc(SCCO)cc1Cl | null | null | null |
1,250,430 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [F:1][C:2]([F:23])([F:22])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.[N+:31]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37](Cl)=[O:38])([O-:33])=[O:32]>ClCCl>[F:23][C:2]([F:22])([F:1])[C:3]([C:9]1[CH:10]... | OC(c1ccc(CN2CCNCC2)cc1)(C(F)(F)F)C(F)(F)F | O=C(Cl)c1cccc([N+](=O)[O-])c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 2 | To a stirred mixture of 1,1,1,3,3,3-hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)-propan-2-ol (3.21 mmol, 1.1 g) and triethylamine (3.21 mmol, 0.448 mL, 0.325 g) in dichloromethane at 0° C. was added 3-nitrobenzoyl chloride (3.21 mmol, 0.596 g). The reaction was stirred at 0° C. for 2 hours then was allowed to warm to ... | O=C(c1cccc([N+](=O)[O-])c1)N1CCN(Cc2ccc(C(O)(C(F)(F)F)C(F)(F)F)cc2)CC1 | null | 53.9 | null |
1,468,909 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [C:1]([O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1(C=CC(O)=CC=1)O.[CH2:21]=[C:22]1[O:26][C:24](=[O:25])[CH2:23]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:26]=[C:22]([CH3:21])[CH2:23][C:24]([O:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[O:25] | C=C1CC(=O)O1 | C=C(C)C(=O)OCC(C)(C)CO | null | CN(C)c1ccncc1 | Oc1ccc(O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 2.5 | 8 | To a 2-L flask was charged neopentyl glycol (208.3 g, 2.0 moles), toluene (250 mL), hydroquinone (0.5 g) and sodium methoxide (25% in methanol, 8 g). The mixture was heated to 60-65° C. and methyl methacrylate (120 g, 1.2 moles) was added dropwise over 1 hour. The reaction was held at 70° C. for one hour under moderate... | C=C(C)C(=O)OCC(C)(C)COC(=O)CC(C)=O | null | null | null |
683,357 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | Cl[C:2]1[NH:11][C:5]2=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=[C:4]2[N:3]=1.[NH:12]1[CH2:17][CH2:16][C:15]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[O:18]2)[CH2:14][CH2:13]1.O>CN1C(=O)CCC1>[Cl:10][C:7]1[N:6]=[C:5]2[NH:11][C:2]([N:12]3[CH2:17][CH2:16][C:15]4([C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)... | Clc1ccc2nc(Cl)[nH]c2n1 | O=C1OC2(CCNCC2)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | O | null | null | null | null | null | null | null | null | null | null | null | Heat a solution of 2,5-dichloro-3H-imidazo[4,5-b]pyridine (0.07 g, 0.37 mmol) and spiro[isobenzofuran-1,4′-piperidin]-3-one (0.15 g, 0.74 mmol) in dry NMP (3 mL) at 100° C. for 14 hours. Pour the cooled mixture into water (10 mL) and extract twice with EtOAc (10 mL). Wash the combined extracts with brine (10 mL), dry, ... | O=C1OC2(CCN(c3nc4ccc(Cl)nc4[nH]3)CC2)c2ccccc21 | null | null | null |
1,527,809 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Cl.Cl.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:20]([NH2:22])=[O:21])[CH2:14][CH2:13]2)=[CH:4]1.[O:29]1[C:33]2[CH:34]=[CH:35][C:36](/[CH:38]=[CH:39]/[C:40](O)=[O:41])=[CH:37][C:32]=2[CH2:31][CH2:30]1>>[NH:3]... | NC(=O)C(NC1CCC(c2c[nH]c3ccccc23)CC1)C1CCNCC1 | O=C(O)/C=C/c1ccc2c(c1)CCO2 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from the product of Example 1, step J, and trans-3-(2,3-dihydrobenzofuran-5-yl)prop-2-enoic acid, by the method of Example 1, step K, giving a solid that was mostly the more polar cyclohexyl diastereomer by LCMS. Mass spectrum (LCMS, ESI pos.) calcd. for C32H38N4O3: 527 (M+H). Found: 527 | NC(=O)C(NC1CCC(c2c[nH]c3ccccc23)CC1)C1CCN(C(=O)/C=C/c2ccc3c(c2)CCO3)CC1 | null | null | null |
1,195,996 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | COC1C=C(C(F)(F)[F:10])C=C([N+]([O-])=O)C=1.[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:26]([F:32])([F:31])C(F)(F)F)=[C:23]([OH:25])[CH:24]=1)([O-:18])=[O:17]>>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:26]([F:31])([F:32])[F:10])=[C:23]([OH:25])[CH:24]=1)([O-:18])=[O:17] | O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(O)c1 | COc1cc([N+](=O)[O-])cc(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5-Nitro-2-trifluoromethyl-phenol was prepared from 1-Methoxy-3-nitro-5-trifluoromethyl-benzene similar to that described in the preparation of 5-nitro-2-pentafluoroethylphenol. | O=[N+]([O-])c1ccc(C(F)(F)F)c(O)c1 | null | null | null |
1,295,577 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[C:19]([C:21]([O:23]C)=[O:22])[N:18]=[CH:17]4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:25])[C:8](=[O:26])[C@H:7]2[CH2:27][CH3:28])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(=O)C.Cl>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[N:18]=[CH:17]4)[N:12]=[C... | CC[C@@H]1C(=O)N(C)c2cnc(-n3cnc(C(=O)OC)c3)nc2N1C1CCCC1 | null | null | Cl | 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 | 100 | null | The title compound was prepared by dissolving (R)-methyl 1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazole-4-carboxylate (Example 38, 0.51 g, 1.33 mmol) in 2 mL of acetic acid and 0.5 mL of concentrated aqueous HCl and heating the resulting solution to 100° C. for 4 hours. The soluti... | CC[C@@H]1C(=O)N(C)c2cnc(-n3cnc(C(=O)O)c3)nc2N1C1CCCC1 | null | null | null |
1,335,927 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[C:33]([CH:40]([OH:43])[CH2:41][CH3:42])[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:44])[CH2:22][CH2:21]3)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][C:5]=2[O:4][... | CCC(O)c1cc(OC)cc2c1ccc(=O)n2CCN1CCC(N(Cc2ccc3c(c2)OCCO3)C(=O)OC(C)(C)C)CC1 | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To 20 mL of a chloroform solution containing 165 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-(1-hydroxypropyl)-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 115 mg of Dess-Martin Periodinane was added, and stirred at room temperature for 2 hours. To the reaction mixture, aqueous... | CCC(=O)c1cc(OC)cc2c1ccc(=O)n2CCN1CCC(N(Cc2ccc3c(c2)OCCO3)C(=O)OC(C)(C)C)CC1 | null | 69.9 | null |
1,023,057 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].Br.[Br:12][C:13]1[S:17][C:16]([NH2:18])=[N:15][CH:14]=1>N1C=CC=CC=1>[Br:12][C:13]1[S:17][C:16]([N:18]([C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:3])[C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:3])=[N:15][CH:14]=1 | O=C(Cl)Oc1ccccc1 | Nc1ncc(Br)s1 | null | Br | 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 | 3 | Phenyl chloroformate (1.4 ml, 11.0 mmol) was slowly added to a suspension of 5-bromo-thiazol-2-ylamine hydrobromide (1.3 g, 5.0 mmol) in 20 ml pyridine under an argon atmosphere. The reaction mixture was stirred for 3 h at room temperature and then concentrated under reduced pressure. The residue was suspended in water... | O=C(Oc1ccccc1)N(C(=O)Oc1ccccc1)c1ncc(Br)s1 | null | 109.7 | null |
1,138,129 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[N:24]([CH2:34][CH3:35])[C:25]4[C:30]([CH:31]=3)=[C:29]([Cl:32])[C:28]([Cl:33])=[CH:27][CH:26]=4)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.Cl.O1CCOCC1>[ClH:32].[N:11]1([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23... | CCn1c(C(=O)Nc2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2)cc2c(Cl)c(Cl)ccc21 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 24 | A mixture of 4-{4-[(4,5-dichloro-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (750 mg, 1.45 mmol) in 15 mL of methylene chloride and 2 mL of 4M hydrogen chloride in dioxane was stirred at room temperature for 24 hr. The solvent was removed to afford 4,5-dichloro-1-ethyl-1H-... | CCn1c(C(=O)Nc2ccc(N3CCNCC3)cc2)cc2c(Cl)c(Cl)ccc21 | null | 212.8 | null |
1,280,061 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([OH:23])=O)=[N:19][CH:20]=1.[CH2:24]([NH2:26])[CH3:25]>>[CH2:24]([NH:26][C:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)=[N:5][O:6][C... | CCN | Cc1onc(-c2ccccn2)c1COc1ccc(C(=O)O)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described for example 7, 5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid (100 mg, 0.32 mmol) was converted, using ethylamine (2 M solution in THF) instead of isopropylamine, to the title compound (93 mg, 85%), which was obtained as a white solid. MS: m/e=339.1 [M+H]+. | CCNC(=O)c1ccc(OCc2c(-c3ccccn3)noc2C)cn1 | null | 85 | null |
944,503 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [CH2:1]([N:3]([CH2:37][CH3:38])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:9]=[C:10]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=2[CH3:36])[C:30]([OH:32])=O)[C:11]2[CH:17]=[CH:16][C:15](=[O:18])[N:14]([C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=3[F:26])[C:12]=2[N:13]=1)[CH3:2].[CH3:39][N:40](C(ON1N=NC2C=CC=CC1=2)=[N+](C... | CN(C)C(On1nnc2ccccc21)=[N+](C)C | CCN(CC)CCCNc1nc(-c2cc(C(=O)O)ccc2C)c2ccc(=O)n(-c3c(F)cccc3F)c2n1 | null | CN | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | To the compound 3-[2-{[3-(diethylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylbenzoic acid (40 mg, 0.074 mmol) in dichloromethane (2 mL) were added HBTU (30 mg, 0.079 mmol) and methylamine (0.185 mL, 0.37 mmol, 2.0M soln in THF). The mixture was stirred at rt overnigh... | CCN(CC)CCCNc1nc(-c2cc(C(=O)NC)ccc2C)c2ccc(=O)n(-c3c(F)cccc3F)c2n1 | null | 80.9 | null |
168,770 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[CH2:20]([N:23]=[C:24]=[O:25])[CH2:21][CH3:22].CO>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:24](=[O:25])[NH:23][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=... | Cc1cc(-c2ccc(O)cc2)cc2ccc(=O)[nH]c12 | CCCN=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | null | A solution of 8-methyl-6-[4-hydroxyphenyl]-2-(1H)-quinolone (0.30 g) and n-propylisocyanate (0.5 cm3) was heated under reflux in THF (10 cm3) under nitrogen for 50 hours. Methanol (10 cm3) was then added to dissolve solid material, followed by silica (Merck "MK 60.9385" [Trade Mark]) (10 g), and the volatile material w... | CCCNC(=O)Oc1ccc(-c2cc(C)c3[nH]c(=O)ccc3c2)cc1 | null | null | null |
1,338,080 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:16]=2[C:17]([O:19]C(C)(C)C)=[O:18])=[CH:10][N:9]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][... | Cc1ccc(Nc2ccc(-c3ccncc3Cl)nc2)c(C(=O)OC(C)(C)C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 25 | 1 | The solid residue obtained in step A was dissolved in 3 ml of trifluoroacetic acid and stirred for 1 hour at room temperature. The solvent was evaporated and the solid residue was triturated with an isopropyl ether/hexane mixture. The solid was filtered off affording 0.16 g (yield 62%) of the expected product. | Cc1ccc(Nc2ccc(-c3ccncc3Cl)nc2)c(C(=O)O)c1 | null | 62 | null |
1,024,129 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [F:1][C:2]1[CH:3]=[C:4]([O:17][CH2:18][CH2:19][O:20][CH3:21])[C:5]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>>[F:1][C:2]1[CH:3]=[C:4]([O:17][CH2:18][CH2:19][O:20][CH3:21])[C:5]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[C:6]([CH2:7][OH:8])[CH:11]=1 | COCCOc1cc(F)cc(C(=O)OC)c1OCCOC | 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 | 1 | To a solution of methyl 5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate (0.34 g, 1.13 mmol) at 0° C. was added a solution of lithium aluminum hydride in tetrahydrofuran (1M, 1.2 mL, 1.2 mmol) and the resulting mixture was stirred for one hour. It was then quenched with ethyl acetate (1 mL) and 5% sodium hydroxide sol... | COCCOc1cc(F)cc(CO)c1OCCOC | null | 97.3 | null |
1,512,635 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([NH:13][NH2:14])=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1.[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].C(N(CC)CC)C>C1COCC1>[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[O:12][C:15](=[O:16])[NH:14][N:13]=3)=[CH:10][C:5]2=[N:4][CH:3]=1 | NNC(=O)c1ccn2c(I)cnc2c1 | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 3 | To a solution of 3-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid hydrazide (196 mg, 0.5 mmol) (prepared as described in Example 329 steps a-c) in THF (10 ml) was added carbonyldiimidazole (243 mg, 1.5 mmol) and triethylamine (0.35 ml, 2.5 mmol) and the reaction mixture left to stir for 3 h. The precipitate formed in th... | O=c1[nH]nc(-c2ccn3c(I)cnc3c2)o1 | null | 115.2 | null |
314,224 | ord_dataset-bd998d3fe946475e835418aaf647c00d | null | 1995-01-01T00:08:00 | true | [CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11].[C:12]([C:14]1[CH:23]=[CH:22][C:17]([C:18](=[O:21])[CH2:19]Br)=[CH:16][CH:15]=1)#[N:13]>CC#N>[CH3:1][C:2]1[N:10]=[C:5]2[N:6]([CH2:19][C:18]([C:17]3[CH:22]=[CH:23][C:14]([C:12]#[N:13])=[CH:15][CH:16]=3)=[O:21])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3... | Cc1[nH]c2ncccc2c1C | N#Cc1ccc(C(=O)CBr)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 | A solution of 2,3-dimethylpyrrolo[2,3-b]pyridine (146 mg, 1 mmol) and p-cyanophenacyl bromide (248 mg, 1.1 mmol) in 3 ml CH3CN was refluxed for 1.5 h. The mixture was allowed to cool and the precipitated product filtered off and washed with a small volume of ice cold CCl4 affording 313 mg (85%) pure title compound as t... | Cc1nc2n(CC(=O)c3ccc(C#N)cc3)cccc-2c1C | null | null | null |
979,132 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [F:1][C:2]([F:19])([F:18])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:6]=1[F:17])[OH:4].C(=O)([O-])[O-].[K+].[K+].I[CH2:27][CH2:28][CH3:29]>C(#N)C>[F:19][C:2]([F:1])([F:18])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:27][CH2:28][CH3:29])[CH... | CCCI | OC(c1cccc(C2CCNCC2)c1F)C(F)(F)F | null | O=C([O-])[O-] | [K+] | 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 | Preparation according to Example 1: 2,2,2-trifluoro-1-(2-fluoro-3-piperidin-4-ylphenyl)ethanol (0.01 g), acetonitrile (2 ml), potassium carbonate (0.01 g) and iodopropane (0.01 g). MS m/z (rel. intensity, 70 eV) 319 (M+, 4), 291 (14), 290 (bp), 220 (3), 149 (3). | CCCN1CCC(c2cccc(C(O)C(F)(F)F)c2F)CC1 | null | null | null |
224,658 | ord_dataset-1d5bba1436bd42b7a27c43833c25d871 | null | 1991-01-01T00:03:00 | true | [OH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=... | CC(=O)OC(C)=O | COc1ccc(-c2sc(-c3ccccc3)cc2O)cc1 | 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 | 4 | 3-Hydroxy-2-(4'-methoxyphenyl)-5-phenylthiophene (200 mg, 0.71 mmol) was dissolved in 2.0 mL of pyridine and treated with acetic anhydride (0.50 mL, 5.3 mmol). The solution was stirred 4 hours at 25° C., and then most of the acetic anhydride and pyridine were removed on a rotary evaporator at reduced pressure. The resi... | COc1ccc(-c2sc(-c3ccccc3)cc2OC(C)=O)cc1 | null | null | null |
1,287,361 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Cl[C:2]1[C:7]2[C:8](=[O:22])[C:9]3[CH:10]=[C:11]([C:16]4[CH:17]=[N:18][CH:19]=[N:20][CH:21]=4)[CH:12]=[CH:13][C:14]=3[O:15][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH3:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][OH:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][O:27][C:2]1[C:7]2[C:8](=[... | CC(C)(C)CCO | O=c1c2cc(-c3cncnc3)ccc2oc2ccnc(Cl)c12 | null | O=C([O-])[O-] | [Cs+] | 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 | 100 | 5 | A resealable tube was charged with 1-chloro-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-one (0.320 g, 1.033 mmol), 3,3-dimethyl-1-butanol (0.260 mL, 2.066 mmol), cesium carbonate (0.842 g, 2.58 mmol), and acetonitrile (10.0 mL). The system was flushed with argon, the tube was sealed, and the mixture stirred at 100... | CC(C)(C)CCOc1nccc2oc3ccc(-c4cncnc4)cc3c(=O)c12 | null | null | null |
34,413 | ord_dataset-2e96d163c3f64eb5b470e1ea1a41922a | null | 1977-01-01T00:12:00 | true | [H-].[Na+].Cl.[CH2:4]1[O:17][C:16]2[C:6](=[CH:7][C:8]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10][C:9]=3[CH:15]=2)[O:5]1.[F:18][C:19]1[CH:30]=[CH:29][C:22]([C:23]([CH2:25][CH2:26][CH2:27][Cl:28])=[O:24])=[CH:21][CH:20]=1.O>CN(C=O)C>[ClH:28].[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([CH2:25][CH2:26][CH2:27][N:12]2[CH2:13][C... | c1c2c(cc3c1OCO3)CCNCC2 | O=C(CCCCl)c1ccc(F)cc1 | null | Cl | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | null | The sodium hydride obtained by washing 1.95 g of the 54% dispersion (0.042 moles) with benzene was used to prepare the sodium salt from 4.54 g. of 2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-3-benzazepine hydrochloride in 50 ml of DMF as described in Example 35. Treatment of the suspension with 4.41 g of 3-(4-fluorobenzoy... | O=C(CCCN1CCc2cc3c(cc2CC1)OCO3)c1ccc(F)cc1 | null | null | null |
525,783 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | C[O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=3)[O:15][CH2:14][C@H:13]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:8][CH:7]=1.Cl>[OH-].[K+].CO>[OH:22][C:18]1[CH:17]=[C:16]2[C:21]([C@H:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:29... | COC(=O)COc1ccc([C@H]2c3ccc(O)cc3OC[C@H]2c2ccccc2)cc1 | null | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 1 | (+,−) cis [4-(7-Hydroxy-3-phenyl-chroman-4-yl)-phenoxy]-acetic acid methyl ester (30 mg, 0.077 mmol) was stirred in 2N potassium hydroxide in methanol (1 ml) for 120 min. The reaction mixture was acidified by 1 N hydrochloric acid (2.5 ml), and stirring continued for 60 min. The precipitated product was filtered, washe... | O=C(O)COc1ccc([C@H]2c3ccc(O)cc3OC[C@H]2c2ccccc2)cc1 | null | null | null |
1,505,048 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12](=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][C:18]([CH3:27])([CH3:26])[NH:17]2)[C:13]([NH2:15])=[O:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:28](=O)([O-])[O-].[Na+].[Na+].CI>C(#N)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]=[N:11][C:12](=[C:16]2[C:25]3[C:20]... | O=C([O-])[O-] | CC(=O)c1ccc(N=NC(C(N)=O)=C2NC(C)(C)Cc3ccccc32)cc1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CI | null | null | null | null | null | null | null | null | null | 25 | null | 2-(4-acetyl-phenylazo)-2-(3,3-dimethyl-3,4-dihydro-2H-isoquinoline-1-ylidene) acetamide (Asinex Corp., Russia) and sodium carbonate are added to acetonitrile, and an acetonitrile solution of methyl iodide is slowly dropped and refluxed. The refluxed product is cooled to room temperature and, then, the solvent is remove... | CC(=O)c1ccc(N=NC(C(N)=O)=C2c3ccccc3CC(C)(C)N2C)cc1 | null | null | null |
3,448 | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | null | 1976-01-01T00:03:00 | true | [CH3:1][CH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH2:3]1.[BH4-].[Na+]>CO.O>[OH:16][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH:4]=2)=[CH:9][CH:10]=1)[CH3:15] | CC(=O)c1ccc(C2=CCC(C)CC2)cc1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | 4 | 8.8 g of para-(4-methyl-1-cyclohexenyl)-acetophenone are stirred portionwise into a solution, cooled to 0°C, of 1.8 g of sodium borohydride in 80 ml of methanol and 15 ml of water. Stirring is continued at 5°-10°C for an hour and a half and at room temperature for 4 hours, 200 ml of water are added, and the batch then ... | CC1CC=C(c2ccc(C(C)O)cc2)CC1 | null | null | null |
830,491 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:20][CH2:21][O:22][Si](C(C)C)(C(C)C)C(C)C)[CH2:10][N:11](C)[C:12](=O)OC(C)(C)C)=[CH:5][CH:4]=1)#[N:2].Cl>C1COCC1>[OH:22][CH2:21][CH2:20][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[CH2:10][NH:11][CH3:12] | CC(C)[Si](OCCC(CN(C)C(=O)OC(C)(C)C)c1ccc(C#N)cc1)(C(C)C)C(C)C | null | 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 | 8 | tert-Butyl {2-(4-cyanophenyl)-4-[(triisopropylsilyl)oxy]butyl}methylcarbamate (0.37 g) was dissolved in THF (8 mL) at 0° C. Hydrochloric acid (8 ml of 6M solution) was added and the mixture stirred overnight at room temperature. The volatiles were removed by evaporation and then removed azeotropically after the additio... | CNCC(CCO)c1ccc(C#N)cc1 | null | null | null |
1,023,212 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][CH:16]([CH:30]([CH3:32])[CH3:31])[CH2:17][CH:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]3[CH2:21][O:20]3)[CH:13]=2)[N:8]([CH3:33])[CH:7]=1>C(O)(C)C.C(N)(C)C>[OH:20][CH:19]([CH:18]([NH:22][C:23](=[O:29])[O:... | COCCCc1cn(C)c2ccc(CC(CC(NC(=O)OC(C)(C)C)C3CO3)C(C)C)cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | CC(C)N | null | null | null | null | null | null | null | null | null | null | null | A solution of 0.032 g of tert-butyl {3-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-4-methyl-1-oxiranylpentyl}carbamate in 1 ml of isopropanol and 0.044 ml of isopropylamine is stirred at 70° C. On completion of reaction (TLC monitoring), the reaction mixture is concentrated by evaporation, and the residue is adm... | COCCCc1cn(C)c2ccc(CC(CC(NC(=O)OC(C)(C)C)C(O)CNC(C)C)C(C)C)cc12 | null | null | null |
703,835 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[N:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1>C1COCC1>[C:1]1([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | ClN1C=Cc2ccccc2C1 | Br[Mg]c1ccccc1 | 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 | 0.83 | A solution of phenylmagnesium bromide (1M in THF, 3.6 mL, 3.6 mmol) is added to a solution of 2-chloro-isoquinoline (258 mg, 1.57 mmol)) and Fe(acac)3 (28 mg, 0.078 mmol) in THF (10 mL) at −30° C. After stirring for 50 min at that temperature, the reaction is quenched with brine, the aqueous layer is extracted with Et2... | C1=CN(c2ccccc2)Cc2ccccc21 | null | 56.5 | null |
1,400,857 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:17]([Sn:21]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])Cl)[CH2:18][CH2:19][CH3:20].[NH4+].[Cl-]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Sn:21]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29... | CCCC[Sn](Cl)(CCCC)CCCC | Clc1ccc2c(I)n[nH]c2c1 | null | CC(C)[Mg]Cl | [Cl-] | [NH4+] | 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 | 20 | 0.33 | To a solution of 6-chloro-3-iodo-1H-indazole (337 mg, 1.21 mmol) in dry tetrahydrofuran (20 mL) was added drop-wise isopropylmagnesium chloride (1.33 mL, 2M in THF, 2.66 mmol) at −16° C. under N2 atmosphere. After stirring for 20 minutes, tributylchlorostannane (472 mg, 1.45 mmol) was added drop-wise at −16° C., and th... | CCCC[Sn](CCCC)(CCCC)c1n[nH]c2cc(Cl)ccc12 | null | 77.3 | null |
474,467 | ord_dataset-d56f0a7ec215495c92e641d9fa932d28 | null | 2000-01-01T00:09:00 | true | [CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([C:15]([OH:17])=O)[CH:12]=[C:13]([CH3:14])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1.Cl.[NH2:19][C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32](=[O:45])[C@@H:33]([CH2:35][CH2:36][CH2:37][NH:38][C:39]([NH2:44])=[N:40][N+:41]([O-:43])=[O:42])[NH2:34])=[CH:26][... | Cc1cc(C(=O)O)cc2c1nc(C1CC1)n2C | NC(=O)NCc1ccc(CNC(=O)[C@H](N)CCCNC(N)=N[N+](=O)[O-])cc1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | Cl | F[B-](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 | Prepared analogously to Example 69a) from 2-cyclopropyl-1,4-dimethyl-1H-benzimidazole-6-carboxylic acid, (R)-N-[[4-(aminocarbonylaminomethyl)phenyl]methyl]-N5 -[amino(nitroimino)methyl]-ornithinamide-hydrochloride and TBTU in a yield of 51% of theory. | Cc1cc(C(=O)N[C@H](CCCNC(N)=N[N+](=O)[O-])C(=O)NCc2ccc(CNC(N)=O)cc2)cc2c1nc(C1CC1)n2C | null | 51 | null |
1,494,751 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [Mg].Br[C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.II.[CH3:13][N:14]([CH3:22])[CH2:15][C@H:16]([CH3:21])[C:17](=[O:20])[CH2:18][CH3:19]>O1CCCC1>[CH3:13][N:14]([CH3:22])[CH2:15][C@H:16]([CH3:21])[C@:17]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1)([OH:20])[CH2:18][CH3:19] | CCC(=O)[C@@H](C)CN(C)C | COc1cccc(Br)c1 | null | II | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 71.5 | null | In a dry flask charged magnesium turning (41.0 gm 1.70 M) in tetrahydrofuran (200 ml). Under nitrogen atmosphere charged 3-Bromo anisole (20.0 gm; 0.106 M), iodine crystal (0.2 gm). Stirred and heated the reaction mass to 68-75° C. After initiation of the reaction the remaining quantity of 3-Bromo anisole (307 gm, 1.64... | CC[C@](O)(c1cccc(OC)c1)[C@@H](C)CN(C)C | null | 79.77 | null |
187,752 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | [CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:17]([O-])=O)[C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.[H][H]>[Ni].C(O)C>[NH2:17][C:9]1[C:10]([F:16])=[C:11]([F:15])[C:12]([F:14])=[C:13]2[C:8]=1[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O... | CCOC(=O)c1cn(C2CC2)c2c(F)c(F)c(F)c([N+](=O)[O-])c2c1=O | [H][H] | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A suspension of 1.9 g (5.3 mmoles) of ethyl 1-cyclopropyl-5-nitro-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 0.5 g of Raney nickel and 100 ml of ethanol was shaken in a hydrogen atmosphere at pressures of 42.5-50 psi and temperatures of 24°-26.5° C. for ten hours. The mixture was filtered through Celite ... | CCOC(=O)c1cn(C2CC2)c2c(F)c(F)c(F)c(N)c2c1=O | null | 34.7 | null |
1,170 | ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad | null | 1976-01-01T00:01:00 | true | [Cl:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6].C([Li])CCC.B(F)(F)F.CCOCC.[CH:21]([C:23]([CH3:25])=[O:24])=[CH2:22]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:22][CH2:21][C:23](=[O:24])[CH3:25] | C#CCCCCl | C=CC(C)=O | null | FB(F)F | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 0.25 | 14.85 Parts of 5-chloropent-1-yne is dissolved in 250 parts by volume of toluene and the resulting solution is cooled to approximately -40°. To that solution is then added 62.8 parts by volume of 2.31 M ethereal butyl lithium and stirring is continued for approximately 15 minutes. 6.87 Parts of boron trifluoride ethera... | CC(=O)CCC#CCCCCl | null | null | null |
706,054 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | C(OC(=O)[NH:7][CH2:8][C:9]1[N:10]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:11](=[O:30])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]1[O:29][CH:28]=[N:27][CH:26]=1)=[CH:14][CH:13]=2)(C)(C)C.[ClH:36]>CO.C(OCC)(=O)C>[ClH:36].[NH2:7][CH2:8][C:9]1[N:10]([CH2:31][CH:32]([CH3:34])[CH3:... | CC(C)Cn1c(CNC(=O)OC(C)(C)C)c(-c2ccccc2)c2cc(-c3cnco3)ccc2c1=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | 25 | 1 | Tert-butyl[2-isobutyl-6-(1,3-oxazol-5-yl)-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.14 g, 0.30 mmol) was dissolved in methanol (4 mL) and a solution (10 mL) of 4N hydrogen chloride in ethyl acetate were added thereto. This mixture was stirred at room temperature for 1 h and the precipitated crystals... | CC(C)Cn1c(CN)c(-c2ccccc2)c2cc(-c3cnco3)ccc2c1=O | null | 69 | null |
136,082 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:29](Cl)(=[O:33])[O:30][CH2:31][CH3:32]>CC1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:1... | O=C(c1ccc(F)cc1)C1(c2ccccc2)CCN(Cc2ccccc2)CC1 | CCOC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 5 | To a stirred mixture of 79 parts of (4-fluorophenyl)[4-phenyl-1-(phenylmethyl)-4-piperidinyl]methanone and 630 parts of methylbenzene were added dropwise 32 parts of ethyl carbonochloridate at room temperature. Upon completion, stirring was continued for 5 hours at reflux temperature. The reaction mixture was evaporate... | CCOC(=O)N1CCC(C(=O)c2ccc(F)cc2)(c2ccccc2)CC1 | null | null | null |
1,400,729 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])=[O:12])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1.[CH3:27][O:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][N:30]=1.CC(C)([O-])C.[Na+]>O1CCOCC1.CC(C)([P](C(C)(C)... | COc1n[nH]c2ccccc12 | CC(C)(CO)NC(=O)c1cn(COCC[Si](C)(C)C)c2ncc(Br)nc12 | null | CC(C)(C)[P]([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C | CC(C)(C)[O-] | [Na+] | 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 | 125 | null | To a stirred solution of 2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 338 μmol), 3-methoxy-1H-indazole (50.1 mg, 338 μmol) in dioxane (2 mL) was added sodium tert-butoxide (71.5 mg, 744 μmol) and bis(tri-tert-butylphosphine)palladium(0) ... | COc1nn(-c2cnc3c(n2)c(C(=O)NC(C)(C)CO)cn3COCC[Si](C)(C)C)c2ccccc12 | null | 80 | null |
1,662,372 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [OH:1][C:2]1[C:11]([O:12]C)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6](C(OC(C)(C)C)=O)[CH2:7]2.B(Br)(Br)Br>ClCCl>[OH:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH2:7]2 | COc1ccc2c(c1O)CCN(C(=O)OC(C)(C)C)C2 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | null | Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tert-butyl 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (70 mg, 0.25 mmol, 1.00 equiv) and dichloromethane (30 mL). This was followed by the addition of BBr3 (187 mg) dropwise with stirri... | Oc1ccc2c(c1O)CCNC2 | null | null | null |
1,338,564 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:30])[CH2:13][CH2:12][N:11]([C:14]([C@H:16]3[CH2:19][CH2:18][C@H:17]3[NH:20]C(=O)OC(C)(C)C)=[O:15])[CH2:10][C:9]2([CH3:29])[CH3:28])=[CH:4][CH:3]=1.O1CCOCC1>Cl>[ClH:1].[NH2:20][C@H:17]1[CH2:18][CH2:19][C@H:16]1[C:14]([N:11]1[CH2:12][CH2:13][C@@:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H]1C(=O)N1CC[C@](O)(c2ccc(Cl)cc2)C(C)(C)C1 | 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 | A solution of tert-butyl (±)-(cis)-2-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidine-1-carbonyl)cyclobutylcarbamate (160 mg, 0.366 mmol) in 4 M HCl in dioxane (5 mL, 20.00 mmol HCl) was stirred at room temperature for 3 hours. After this time, the mixture was concentrated in vacuo, then concentrated 3× from me... | CC1(C)CN(C(=O)[C@@H]2CC[C@@H]2N)CC[C@]1(O)c1ccc(Cl)cc1 | null | null | null |
1,615,248 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Si:1]([O:18][CH2:19][CH2:20][C@H:21]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)[CH2:22][C@H:23]1[O:28][C@@H:27]([CH2:29][C@@H:30]([O:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:26][C@@H:25]([OH:42])[CH2:24]1)([C:14]([CH3:17])([CH3:16])[CH3... | C[Si](C)(C)Cl | CCOC(=O)C[C@@H](C[C@H]1C[C@@H](O)C[C@@H](C[C@H](CCO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)OCc2ccc(OC)cc2)O1)O[Si](C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 12 | To a solution of alcohol 4 (83.1 mg, 0.111 mmol, 1.0 equiv) in CH2Cl2 (11 mL, 0.01 M) in a 25 mL rb flask was added TMSCl (60.3 mg, 0.555 mmol, 5.0 equiv) and NEt3 (112.3 mg, 1.11 mmol, 10.0 equiv) dropwise via syringe. After 12 h at rt, the reaction was quenched by the addition of water (5.0 mL). The phases were separ... | CCOC(=O)C[C@@H](C[C@H]1C[C@@H](O[Si](C)(C)C)C[C@@H](C[C@H](CCO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)OCc2ccc(OC)cc2)O1)O[Si](C)(C)C | null | 95.9 | null |
370,453 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | [CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:7]([C:13]([O:15]CC)=[O:14])=[C:8]([CH:10]([OH:12])[CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].O.[OH-].[Li+]>>[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22](... | CCCCc1nc(C(C)O)c(C(=O)OCC)n1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | Following a procedure similar to that described in Example 36, 0.54 g of ethyl 2-butyl-4-(1-hydroxyethyl)-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in Example 43(b)] was hydrolyzed, using 245 mg of lithium hydroxide monohydrate, to give 0.43 g of the title compound as a p... | CCCCc1nc(C(C)O)c(C(=O)O)n1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | null | 84.6 | null |
1,564,365 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=O)[CH:7]=1.[CH3:17][NH:18][NH2:19]>O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:18]([CH3:17])[N:19]=[C:8]2[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1 | CNN | O=C(c1cccnc1)c1cc(Br)ccc1F | null | null | 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 | 100 | null | A heavy wall pressure flask was charged with (5-bromo-2-fluorophenyl)(pyridin-3-yl)methanone (3.417 g, 12.2 mmol) and dioxane (30 mL). Methylhydrazine (1.4 mL, 26.6 mmol) was then added, and the mixture was heated to 100° C. for 16 hours. The crude mixture was concentrated, and purified by column chromatography (gradie... | Cn1nc(-c2cccnc2)c2cc(Br)ccc21 | null | null | null |
403,153 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | [F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:38]=[N+:39]=[N-])(=O)=O)(C)C.N12CCCN=C1CCCCC2>C(#N)C>[N+:38](=[C:13]([C:5]1[CH:4]=[C:3]([C:2]([F:18])([F:19])[F:1])[CH:8]=[C:7]([C:9]([F:11])([F:12])[F:10]... | COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CC(C)c1cc(C(C)C)c(S(=O)(=O)N=[N+]=[N-])c(C(C)C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | -5 | 1 | To methyl 3,5-bis(trifluoromethyl)phenylacetate (43.5 g, 160 mmol), in dry acetonitrile (250 ml), cooled to -5° C., was added 2,4,6-triisopropyl benzenesulfonyl azide (52.7 g). To the resulting solution was added 1,8-diazabicyclo[5.4.0]undec-7-ene (25.5 ml), and the mixture was stirred at -5° C. for 1 hour. The mixture... | COC(=O)C(=[N+]=[N-])c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | null |
947,489 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH:12](N(C(C)C)CC)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C.CO>[CH3:12][O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1 | CCN(C(C)C)C(C)C | O=[N+]([O-])c1ccc(O)cc1F | null | C[Si](C)(C)C=[N+]=[N-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC#N | null | null | null | null | null | null | null | null | null | 25 | 18 | A solution of 3-fluoro-4-nitrophenol (25 g, 0.159 mmol) in acetonitrile (500 mL) and methanol (500 mL) was treated with diisopropyl ethylamine (28 mL). The reaction mixture was cooled in an ice-bath and after 30 minutes, trimethylsilyldiazomethane was added dropwise. The mixture was stirred at room temperature for 18 h... | COc1ccc([N+](=O)[O-])c(F)c1 | null | 100 | null |
109,648 | ord_dataset-406d20cb3f314e2c967b14f55925f895 | null | 1983-01-01T00:10:00 | true | [CH2:1]([N:19]=[C:20]=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:22]([OH:25])[CH2:23][OH:24]>N1C=CC=CC=1>[CH2:1]([NH:19][C:20]([O:24][CH2:23][CH2:22][OH:25])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][... | CCCCCCCCCCCCCCCCCCN=C=O | OCCO | 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 | null | 8 | In 50 ml of pyridine are dissolved 11.8 g (40 mM) of stearyl isocyanate and 12.4 g (200 mM) of ethylene glycol, and the solution is allowed to stand at room temperature overnight. The reaction mixture is concentrated to dryness under reduced pressure, and the residue is recrystallized from 100 ml of methanol to give 11... | CCCCCCCCCCCCCCCCCCNC(=O)OCCO | null | 79.7 | null |
1,475,368 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | O1CCOCC1.C(OC([N:14]1[CH2:17][CH:16]([N:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[CH:25][C:26]4[N:27]([C:29]([CH2:32][C:33]5[CH:34]=[C:35]6[C:40](=[CH:41][C:42]=5[F:43])[N:39]=[CH:38][CH:37]=[CH:36]6)=[CH:30][N:31]=4)[N:28]=3)[CH:20]=[N:19]2)[CH2:15]1)=O)(C)(C)C.Cl>CCOC(C)=O.C([O-])(O)=O.[Na+]>[NH:14]1[CH2:15][CH:16]([N:18]2[... | CC(C)(C)OC(=O)N1CC(n2cc(-c3ccc4ncc(Cc5cc6cccnc6cc5F)n4n3)cn2)C1 | null | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 1 | Dioxane (5 mL) was charged in a flask. 3-{4-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-azetidine-1-carboxylic acid tert-butyl ester (Stage 146.2, 100 mg, 0.200 mmol) and HCl in dioxane (4 M solution, 500 μL, 2.002 mmol) were then added and the mixture was stirred at rt for 1 h. The RM... | Fc1cc2ncccc2cc1Cc1cnc2ccc(-c3cnn(C4CNC4)c3)nn12 | null | null | null |
129,624 | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | null | 1985-01-01T00:05:00 | true | [CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:12]=1[O:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:25])[N:10]([CH3:28])[C:11]1[C:12]([O:23][CH3:24])=[CH:13][C:14]([C:19]([O:21][CH3:22])=... | CI | COC(=O)c1cc(OC)c(NC(=O)OCc2ccccc2)c(OC)c1 | 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 | 25 | 1 | A suspension of 34.2 g. of 2,6-dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester and 5.8 g. of sodium hydride (50% dispersion in oil) in 300 ml. of absolute dimethylformamide was stirred at room temperature for 4 hours. The resulting solution was treated with 17 g. of methyl iodide with stirring and ice-cooli... | COC(=O)c1cc(OC)c(N(C)C(=O)OCc2ccccc2)c(OC)c1 | null | null | null |
766,425 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([N+:21]([O-])=O)[CH:3]=1>CO.Cl.[Fe]>[NH2:21][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]1=[O:20] | Cn1c(C(F)(F)F)cc(=O)n(-c2ccc(Cl)cc2[N+](=O)[O-])c1=O | null | null | [Fe] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred suspension of 3-(4-chloro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (1 g) in methanol (20 ml) and conc. hydrochloric acid (10 ml) was added iron (powdered, 0.48 g) unded vigorous stirring. After addition, the mixture was heated at reflux temperature for 1 hr. The oil bath was re... | Cn1c(C(F)(F)F)cc(=O)n(-c2ccc(Cl)cc2N)c1=O | null | null | null |
1,298,622 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[C:4]([Cl:12])[CH:3]=1.[CH3:13][N:14]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH2:16][C:15]1=[O:24].[Al+3].[Cl-].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:21]2[CH:22]=[CH:23][C:18]3[O:17][CH2:16][C:15](=[O:24])[N:14]([CH3:13])[C:19]=3... | O=C(O)Cc1ccc(Br)cc1Cl | CN1C(=O)COc2ccccc21 | null | [Al+3] | [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 | In analogy to Example 1, step 1, (4-bromo-2-chloro-phenyl)-acetic acid was converted to the acid chloride and subsequently reacted with 4-methyl-2H-1,4-benzoxazin-3(4H)-one in the presence of AlCl3 to give the title compound as a light brown solid. MS (m/e, ISP neg. ion)=392.1 [M−H+]. | CN1C(=O)COc2ccc(C(=O)Cc3ccc(Br)cc3Cl)cc21 | null | null | null |
598,404 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | [CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH2:12]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:2]=1[CH3:1])[C:13]1[CH:18]=[CH:17][CH... | Cc1c(N)cccc1[N+](=O)[O-] | O=Cc1ccccc1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 4 | 2-Methyl-3-nitroaniline (3.40 g, 22.3 mmoles) and benzaldehyde (3.9 mL, 38 mmoles) in dichloroethane (78 mL) were treated with glacial acetic acid (5.1 mL, 89 mmoles). The yellow reaction mixture was stirred for 4 hours at room temperature, treated with sodium triacetoxyborohydride (9.5 g, 44.6 mmoles) and allowed to s... | Cc1c(NCc2ccccc2)cccc1[N+](=O)[O-] | null | 87.4 | null |
150,885 | ord_dataset-b9a9e369e9da4413999591aa08f4c3e3 | null | 1986-01-01T00:11:00 | true | [F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][C:9]#N)=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:14]>>[F:1][C:2]1[CH:12]=[C:11]2[C:5](=[CH:4][CH:3]=1)[O:6][CH2:7][CH2:8][C:9]2=[O:14] | O=S(=O)(O)O | N#CCCOc1ccc(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 | In the former pathway, 3-(4-fluorophenoxy)propionitrile having the formula (I) is stirred in polyphosphoric acid at a temperature of more than 140° C., preferably at about 170° C. for about 15 minutes to form 6-fluoro-4-chromanimine having the formula (V) and then the reaction mixture is poured into ice-water to hydrol... | O=C1CCOc2ccc(F)cc21 | null | null | null |
27,526 | ord_dataset-14866e68bb5b47f5929457eecb4eb3a5 | null | 1977-01-01T00:07:00 | true | [OH:1][C:2]([CH3:28])([CH2:23][CH2:24][O:25][CH2:26][CH3:27])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH:6]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].O>C(O)(=O)C>[OH:1][C:2]([CH3:28])([CH2:23][CH2:24][O:25][CH2:26][CH3:27])[CH:3]=[CH:4][CH:5]1[CH:6]([CH2:14][CH2:15][CH2:16][CH2... | CCOCCC(C)(O)C=CC1CCC2(OCCO2)C1CCCCCCC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | null | 6 | Crude 7-{7-(3-hydroxy-3-methyl-5-ethoxypent-1-enyl)-1,4-dioxaspiro[4,4]non-6-yl}heptanoic acid (0.38 g.), water (8 ml.) and glacial acetic acid (16 ml.) were left to stand at room temperature for 6 hours. The solution was then evaporated in vacuo at a temperature lower than 50° C. Ethyl acetate (150 ml.) was added, and... | CCOCCC(C)(O)C=CC1CCC(=O)C1CCCCCCC(=O)O | null | 106.5 | null |
1,020,234 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [N:1]1([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[C:25]([O:28][CH2:29][CH:30]3[CH2:33][CH2:32][CH2:31]3)[CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:12][CH2:11]2)[CH2:7][CH2:6][CH2:5][CH2:4]C[CH2:2]1.Cl.Cl.Cl.NC1CCN(CCN2CCC([OH:52])CC2)CC1>>[OH:52][CH:5]1[CH2:6][CH2:7][N... | O=C(NC1CCN(CCN2CCCCCC2)CC1)c1cc2c(OCC3CCC3)cccc2[nH]1 | NC1CCN(CCN2CCC(O)CC2)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound is synthesized analogously to Example 1 from 4-Cyclobutylmethoxy-1H-indole-2-carboxylic acid 82 (preparation see Example 22) and amine 21. | O=C(NC1CCN(CCN2CCC(O)CC2)CC1)c1cc2c(OCC3CCC3)cccc2[nH]1 | null | null | null |
1,147,472 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][N:5]=[C:6]=[O:7].[Cl:12][C:13]1[N:18]=[C:17]2[NH:19][N:20]=[C:21]([OH:22])[C:16]2=[C:15]([CH3:23])[CH:14]=1>C1COCC1.CN(C=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][NH:5][C:6]([N:20]1[C:21](=[O:22])[C:16]2[C:17](=[N:18][C:13]([Cl:12])=[CH:14][C:15]... | Cc1cc(Cl)nc2[nH]nc(O)c12 | Cc1ccccc1CN=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 2 | 136 μl (0.98 mmol) of 2-methylbenzyl isocyanate were added to 150 mg (0.82 mmol) of 6-chloro-4-methyl-1H-pyrazolo[3,4-b]pyridin-3-ol in 10 ml of THF and 2 ml of DMF at room temperature. The reaction mixture was stirred at room temperature for 2 h and left to stand overnight. Concentration was followed by purification b... | Cc1ccccc1CNC(=O)n1[nH]c2nc(Cl)cc(C)c2c1=O | null | null | null |
719,863 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [F:1][C:2]1[CH:10]=[C:9]([C:11]2[N:15]3[CH:16]=[C:17]([C:20]4[CH:21]=[N:22][N:23]([C:25]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH:24]=4)[CH:18]=[CH:19][C:14]3=[N:13][CH:12]=2)[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:... | O=C(O)c1ccc(-c2cnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cn23)cc1F | Cc1csc(N)n1 | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)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 | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 170 mg 2-fluoro-4-[6-(1-trityl-1H-4-pyrazolyl)imidazo-[1,2-a]pyridin-3-yl]benzoic acid (compound in Example 472) and 34.4 mg 2-amino-4-methyl-1,3-thiazole were allowed to react overnight with 146 mg benzotriazol-1-yloxy-tris-(dimethylamino)phosphonium hexafluorophosphate and 50 μL triethylamine in 6 mL dichloromethane.... | Cc1csc(NC(=O)c2ccc(-c3cnc4ccc(-c5cnn(C(c6ccccc6)(c6ccccc6)c6ccccc6)c5)cn34)cc2F)n1 | null | 84.9 | null |
1,699,386 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | IC.[C:3](=O)([O-])[O-].[Cs+].[Cs+].[Cl:9][C:10]1[CH:19]=[C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]>CN(C=O)C>[Cl:9][C:10]1[CH:19]=[C:18]([N:20]([CH3:3])[S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13] | O=C([O-])[O-] | COC(=O)c1ccc(NS(C)(=O)=O)cc1Cl | null | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CI | null | null | null | null | null | null | null | null | null | 25 | 16 | 78 μL of iodomethane and 447 mg of Cesium Carbonate were added to 300 mg of methyl 2-chloro-4-(methylsulfonamido)benzoate in 3 mL of DMF and stirred at room temperature for 16 hours. The reaction mixture was extracted in Ethyl Acetate twice with saturated bicarbonate and once with brine, dried over Magnesium Sulfate, f... | COC(=O)c1ccc(N(C)S(C)(=O)=O)cc1Cl | null | null | null |
1,161,323 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[N:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19])=[CH:3][CH:2]=1.[CH2:28]([N:35]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][CH3:4... | CNCCCCCN(Cc1ccccc1)Cc1ccccc1 | COC(=O)C=Cc1ccccc1N=C=Nc1ccc(-c2ccccc2)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 | Compound (11) is reacted with compound (18) in a suitable solvent to give 3-(4-biphenylyl)-2-[N-(5-dibenzylaminopentyl)-N-methylamino]-4-methoxycarbonylmethyl-3,4-dihydroquinazoline (19). Then, this compound (19) is hydrogenated in the presence of Pd(C) and formalin solution to give 2-[N-(5-N′,N′-dimethylaminopentyl)-N... | COC(=O)CC1c2ccccc2N=C(N(C)CCCCCN(Cc2ccccc2)Cc2ccccc2)N1c1ccc(-c2ccccc2)cc1 | null | null | null |
1,710,991 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | C[Si]([C:5]#[C:6][C:7]1[NH:11][C:10]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:9][CH:8]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:6]([C:7]1[NH:11][C:10]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:9][CH:8]=1... | CC(C)(C)OC(=O)N1CCC[C@H]1c1ncc(C#C[Si](C)(C)C)[nH]1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 3 | (S)-tert-Butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (537 mg, 1.61 mmol) was dissolved into MeOH (20 mL) and then potassium carbonate (22 mg, 0.16 mmol) was added and the reaction was stirred at rt for 3 h. The reaction was concentrated, dissolved into dichcloromethane, loaded onto a... | C#Cc1cnc([C@@H]2CCCN2C(=O)OC(C)(C)C)[nH]1 | null | 82 | null |
1,501,248 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | Cl[C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:9]([C:5]1[C:6]([NH2:8])=[CH:7][C:2]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:3][CH:4]=1)([O-:11])=[O:10] | Nc1cc(Cl)ncc1[N+](=O)[O-] | C1CCNC1 | null | O=C([O-])[O-] | [K+] | 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 | 70 | null | A 500 mL round bottom flask equipped with a reflux condenser was charged with 2-chloro-5-nitropyridin-4-amine (2.00 g, 11.5 mmol, 1.0 equiv), pyrrolidine (2.86 mL, 34.6 mmol, 3.0 equiv), potassium carbonate (4.78 g, 34.6 mmol, 3.0 equiv) and acetonitrile (50 mL). The mixture was heated at 70° C. overnight under nitroge... | Nc1cc(N2CCCC2)ncc1[N+](=O)[O-] | null | 59.7 | null |
601,802 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:14](=O)[CH2:15]Br>>[CH3:10][C:11]1[CH:12]=[C:13]([C:14]2[N:1]=[C:2]3[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]3[CH:15]=2)[CH:18]=[CH:19][C:20]=1[CH3:21] | COc1ccnc(N)c1 | Cc1ccc(C(=O)CBr)cc1C | null | null | null | null | null | null | null | 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, pale yellow solid, m.p. 175° C. and MS: m/e=252.2 (M+), was prepared in accordance with the general method of example 1 from 2-amino-4-methoxy-pyridine and 3,4-dimethyl-phenacylbromide. | COc1ccn2cc(-c3ccc(C)c(C)c3)nc2c1 | null | null | null |
1,214,438 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH3:1][O:2][C:3](=[O:16])[C:4](=O)[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([Br:14])[CH:8]=1)Cl.[C:17]([NH2:20])(=[S:19])[CH3:18]>>[CH3:1][O:2][C:3]([C:4]1[N:20]=[C:17]([CH3:18])[S:19][C:5]=1[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([Br:14])[CH:8]=1)=[O:16] | CC(N)=S | COC(=O)C(=O)C(Cl)c1ccc(F)c(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | prepared by reaction of 3-(3-Bromo-4-fluoro-phenyl)-3-chloro-2-oxo-propionic acid methyl ester with thioacetamide. LC-MS: tR=0.95 min; [M+H]+=330.2. | COC(=O)c1nc(C)sc1-c1ccc(F)c(Br)c1 | null | null | null |
279,389 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | N.[CH2:2]([C@@H:8]1[C:11](=[O:12])[O:10][C@H:9]1[CH2:13][C@@H:14]([O:26][CH2:27][CH2:28][C:29]([OH:31])=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C[N:33](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[C:29]([CH2:28][CH2:27... | CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OCCC(=O)O | CN(C)C(On1nnc2ccccc21)=[N+](C)C | null | F[P-](F)(F)(F)(F)F | N | 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 | Ammonia gas was blown into a solution of 40 mg of 3-[[(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl]oxy]propionic acid (Example L) in 2.5 ml of acetonitrile until the solution is saturated and subsequently 50 mg of HBTU were added. Then, the mixture was filtered and evaporated and the residue was chromato-gra... | CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OCCC(N)=O | null | 81.4 | null |
1,702,155 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([Cl:17])[CH:3]=1.[NH2:18][C:19]1[N:24]=[CH:23][C:22](B(O)O)=[CH:21][N:20]=1>>[NH2:18][C:19]1[N:24]=[CH:23][C:22]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[C:7]([CH3:16])[C:6]=3[CH:5]=[C:4]([Cl:17]... | Cc1c2n(c3c(Br)cc(Cl)cc13)CCNC2=O | Nc1ncc(B(O)O)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, white solid (59 mg, 72%), MS (ISP) m/z=328.5 [(M+H)+], mp 316° C., was prepared in accordance with the general method of example 1 from 6-bromo-8-chloro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (intermediate 12) (78.4 mg, 0.25 mmol) and commercially available 2-aminopyrimidin-5-ylboronic ... | Cc1c2n(c3c(-c4cnc(N)nc4)cc(Cl)cc13)CCNC2=O | null | null | null |
345,784 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH3:10].N1C=CC=CC=1.[CH3:17][C:18](=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19](Cl)=[O:20]>CC(C)=O>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([CH3:10])=[C:2]([NH:1][C:19](=[O:20])[C:18]([CH3:17])=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2... | CC(=Cc1ccccc1)C(=O)Cl | COc1ccc(C)c(N)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 2-Amino-4-methoxytoluene (13.2 g, 89.7 mmol) and pyridine (10 ml) were dissolved in acetone (112 ml), to which α-methylcinnamoylchloride (19.4 g, 107.6 mmol) was added while cooling and stirring. The mixture was stirred overnight at room temperature. The solvent was evaporated, and the residue was dissolved in chlorofo... | COc1ccc(C)c(NC(=O)C(C)=Cc2ccccc2)c1 | null | 84.3 | null |
192,724 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | [CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[N:6][NH:5][C:4](=[O:15])[CH2:3]1.[CH3:16][N:17]=[C:18]=[O:19]>CS(C)=O>[CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:18]([NH:17][CH3:16])=[O:19])=[N:12][CH:13]=2)=[N:6][NH:5][C:4](=[O:15])[CH2:3]1 | CN=C=O | CC1CC(=O)NN=C1c1ccc(N)nc1 | null | null | null | 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 | null | null | A mixture of 0.4 g. (2 mmole) 4,5-dihydro-5-methyl-6-(2-amino-5-pyridyl)-3(2H)-pyridazinone, 10 ml. dimethyl sulphoxide and 0.24 ml. (4 mmole) methyl isocyanate was stirred for 16 hours at ambient temperature, evaporated in a vacuum and the residue triturated with water. There were obtained 0.25 g. of the title compoun... | CNC(=O)Nc1ccc(C2=NNC(=O)CC2C)cn1 | null | 48 | null |
917,781 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:30]=[CH:29][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:28])[CH2:25][CH2:26][CH3:27])[CH:18]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCCC1>[C:24]([NH:23][C:19]1[CH:18]=[C:17]([O:16][C:15]2[CH:14]=[CH:13][C:12]([NH:11][C:2](... | CCCC(=O)Nc1cc(Oc2ccc(N)cc2)ccn1 | O=C(Cl)Oc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | Phenyl chloroformate (0.14 ml) was added dropwise to an ice-cooled stirred solution of 4-(4-aminophenoxy)-2-(butyrylamino)pyridine (0.3 g), triethylamine (0.14 ml) and tetrahydrofuran (10 ml). The cooling bath was removed and the mixture was stirred at room temperature overnight. Silica gel was added to the reaction so... | CCCC(=O)Nc1cc(Oc2ccc(NC(=O)Oc3ccccc3)cc2)ccn1 | null | null | null |
1,077,345 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].[H-].[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][C:26]2[C:29]([CH2:34]Cl)=[C:30]([Cl:33])[CH:31]=[CH:32][C:25]=2[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[I-].[Na+]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2... | CC(C)(C)OC(=O)N1CCc2ccc(Cl)c(CCl)c2CC1 | CCC(C)(C)c1ccc(S)cc1 | null | [H-] | [I-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 45 | 0.08 | Dissolve 4-(1,1-dimethyl-propyl)-benzenethiol (100 mg, 0.55 mmol) in anhydrous DMF (2 mL). Add sodium hydride (32 mg, 0.78 mmol, 60% dispersion in mineral oil) at room temperature under a nitrogen atmosphere. Stir the mixture for 5 min, then add a solution of 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrah... | CCC(C)(C)c1ccc(SCc2c(Cl)ccc3c2CCN(C(=O)OC(C)(C)C)CC3)cc1 | null | 40.3 | null |
323,729 | ord_dataset-24ad29d930104afea313b6c3bd11099e | null | 1996-01-01T00:01:00 | true | [CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[C:6](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>N1C=CC=CC=1>[C:6]([O:4][CH2:3][CH2:2][CH2:1][OH:5])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | OCCCO | 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 | 18 | To a solution of 76 g of 1,3-propanediol in 0.5 1 of pyridine, cooled to 0° C., were added 278 g of trityl chloride. The mixture was stirred at room temperature for 18 hours, and then the solvent was evaporated in vacuo. The residue was taken up in 600 ml of ethyl acetate. Unsoluble material was filtered off, and the f... | OCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | 52.7 | null |
311,880 | ord_dataset-04982f13ed08448d93df6794846500f3 | null | 1995-01-01T00:06:00 | true | [OH:1][C:2]1[C:3]([O:13]CC2C=CC=CC=2)=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]=2[CH:12]=1.[CH:21]1(Br)[CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH:21]1([O:1][C:2]2[C:3]([OH:13])=[CH:4][C:5]3[O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]=3[CH:12]=2)[CH2:25][CH2:24][CH2:23][CH2:22]... | O=c1ccc2cc(O)c(OCc3ccccc3)cc2o1 | BrC1CCCC1 | null | O=C([O-])[O-] | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 3 | 50.0 g (186 mmol) of 6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one, 41.7 g (280 mmol) of cyclopentylbromide, 51.4 g (372 mmol) of potassium carbonate and 5.0 g of potassium iodide are agitated in 500 ml DMF for 18 h at 80° C. This is followed by filtration, evaporation, dissolution in chloroform, washing with water, ... | O=c1ccc2cc(OC3CCCC3)c(O)cc2o1 | null | null | null |
1,215,901 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | C(O)(=O)C.[BH4-].[Na+].[C:7]1([C@@H:13]([NH:15][C:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(#N)C>[C:7]1([C@@H:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:14])[CH:8]=[CH:9]... | CCOC(=O)C1=C(N[C@@H](C)c2ccccc2)CCCC1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CC#N | null | null | null | null | null | null | null | null | null | 23 | null | Acetic acid (1.0 L) was added to a reactor followed by sodium borohydride (100 g) with cooling between 16-30° C. under nitrogen in NLT 1 hour and mixed for NLT 30 minutes. Acetonitrile (500 mL) was added and mixed for NLT 30 minutes, and the cooled to below 5° C. A solution of (S)-ethyl 2-(1-phenylethylamino)cyclohex-1... | CCOC(=O)[C@@H]1CCCC[C@@H]1N[C@@H](C)c1ccccc1 | null | 90 | null |
1,570,623 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH3:1][N:2]1[C:7]2[C:8](C)=[CH:9][NH:10][C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].Br[CH2:16][C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:30]=[C:29]([F:31])[C:28]([O:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[C:27]([Cl:38])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[Cl:38][C:27]1[CH:26]=[C:25]([C:23]... | Cc1c[nH]c2c(=O)n(C)c(=O)n(C)c12 | O=C(CBr)Nc1nc(-c2cc(F)c(OCC(F)(F)F)c(Cl)c2)cs1 | 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 | The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (33 mg, 0.184 mmol) with 2-bromo-N-{4-[3-chloro-5-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]-1,3-thiazol-2-yl}acetamide (70 mg, 0.156 mmol) in the presence of NaH (11 mg, 0.458 mmol) in dry DMF (5.0 mL) to give 11 mg o... | Cn1c(=O)c2c(ccn2CC(=O)Nc2nc(-c3cc(F)c(OCC(F)(F)F)c(Cl)c3)cs2)n(C)c1=O | null | null | null |
37,838 | ord_dataset-b0ddd49dad024fc7a23ae6f474f9c52f | null | 1978-01-01T00:03:00 | true | P(Cl)(Cl)[Cl:2].[C:5]1([O:11][P:12](OC2C=CC=CC=2)[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C)P(=O)(N(C)C)N(C)C>[C:5]1([O:11][P:12]([Cl:2])[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1 | c1ccc(OP(Oc2ccccc2)Oc2ccccc2)cc1 | ClP(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)P(=O)(N(C)C)N(C)C | null | null | null | null | null | null | null | null | null | null | 25 | null | 32.5 g (0.24 mole) of phosphorus trichloride is added dropwise, with stirring, to a mixture, cooled to 0° to 5° C, of 155.2 g (0.5 mole) of triphenylphosphite and 10.0 g of hexamethylphosphoric acid triamide. The reaction mixture is subsequently heated to room temperature and stirred at this temperature for a further 4... | ClP(Oc1ccccc1)Oc1ccccc1 | null | 181.4 | null |
1,194,331 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | Cl[C:2]1[N:25]=[CH:24][C:5]2[C:6]3[N:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)[CH:9]=[C:8]([C:14]1[N:18]([CH:19]([CH3:21])[CH3:20])[N:17]=[C:16]([CH2:22][OH:23])[N:15]=1)[N:7]=3.Cl.[F:27][C:28]1([F:32])[CH2:31][NH:30][CH2:29]1>>[F:27][C:28]1([F:32])[CH2:31][N:30]([C:2]2[N:25]=[CH:24][C:5]3[C:6]4[N:10]([CH:9]=[C:8]([C:... | FC1(F)CNC1 | CC(C)n1nc(CO)nc1-c1cn2c(n1)-c1cnc(Cl)cc1OCC2 | 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 | [5-(8-Chloro-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-2-yl)-1-isopropyl-1H-[1,2,4]triazol-3-yl]-methanol was reacted with 3,3-difluoroazetidine-HCl to give 417 (23 mg) as a colorless solid. LCMS: 418.1. 1H NMR (400 MHz, DMSO) δ 9.14 (s, 1H), 7.85 (s, 1H), 6.16 (s, 1H), 5.87 (dt, J=13.2, 6.6 Hz, 1H), 5.18 (t, J=6.... | CC(C)n1nc(CO)nc1-c1cn2c(n1)-c1cnc(N3CC(F)(F)C3)cc1OCC2 | null | null | null |
1,024,569 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | C[O:2][C:3](=[O:94])[CH2:4][N:5]([CH3:93])[C:6](=[O:92])[C@H:7]([C@H:89]([OH:91])[CH3:90])[NH:8][C:9](=[O:88])[C@H:10]([C@H:80]([OH:87])[C@H:81]([CH3:86])[CH2:82]/[CH:83]=[CH:84]/[CH3:85])[N:11]([CH3:79])[C:12](=[O:78])[C@H:13]([CH:75]([CH3:77])[CH3:76])[N:14]([CH3:74])[C:15](=[O:73])[C@H:16]([CH2:69][CH:70]([CH3:72])[... | C/C=C/C[C@@H](C)[C@@H](O)[C@@H](C(=O)N[C@H](C(=O)N(C)CC(=O)OC)[C@@H](C)O)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@H](NC(=O)OC(C)(C)C)C(C)CC | null | null | O=C([O-])O | [Na+] | 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 | 4 | Methyl-(6R,9S,12S,15S,18R,21S,24S,27S,30S,33S)-6-sec-butyl-33-[(1R)-1-hydroxyethyl]-30-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexen-1-yl]-9,12,21,24-tetraisobutyl-27-isopropyl-2,2,11,15,18,20,26,29,35-nonamethyl-4,7,10,13,16,19,22,25,28,31,34-undecaoxo-3-oxa-5,8,11,14,17,20,23,26,29,32,35-undecaazaheptatriacontan-37-oate (80... | C/C=C/C[C@@H](C)[C@@H](O)[C@@H](C(=O)N[C@H](C(=O)N(C)CC(=O)O)[C@@H](C)O)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@H](N)C(C)CC | null | 61.5 | null |
559,659 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([NH:23][OH:24])[CH2:20][CH2:21][CH3:22]>>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[N+:23]([CH2:19][CH2:20][CH2:21][CH3:22])[O-:24])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6... | CCCCNO | COc1cc(C=O)ccc1OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the procedures described in Examples 11 using 4-benzyloxy-3-methoxybenzaldehyde and N-n-butylhydroxylamine. The title compound was isolated in 41.7% yield as a solid, m.p. 81.2° C. | CCCC[N+]([O-])=Cc1ccc(OCc2ccccc2)c(OC)c1 | null | null | null |
888,442 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4][C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)[CH:9]=1.O1CCCC1>[Fe].C(O)(=O)C>[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4][C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])[CH:9]=1 | CC(C)(C)C#Cc1cnn(-c2ccccc2[N+](=O)[O-])c1 | null | null | [Fe] | 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 | 80 | null | A mixture of 4-(3,3-dimethyl-but-1-ynyl)-1-(2-nitro-phenyl)-1H-pyrazole (20 g, 74 mmol), tetrahydrofurane (100 ml) and acetic acid (425 ml of a 5% aqueous solution) was heated to 80° C. Iron powder (66 g, 1.2 mol) was added in small portions at this temperature. The reaction mixture was heated for 5 hours to reflux. Af... | CC(C)(C)C#Cc1cnn(-c2ccccc2N)c1 | null | null | null |
833,697 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [Br:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([Cl:8])=[CH:6][N:7]=1.[Cl:10][C:11]1[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=1>>[Cl:10][C:11]1[S:15][C:14]([S:16]([NH:9][C:3]2[C:2]([Br:1])=[N:7][CH:6]=[C:5]([Cl:8])[N:4]=2)(=[O:18])=[O:17])=[CH:13][CH:12]=1 | Nc1nc(Cl)cnc1Br | O=S(=O)(Cl)c1ccc(Cl)s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by the method of Example 1 using 3-bromo-6-chloro-2-pyrazinamine and 5-chloro-2-thienylsulphonyl chloride. | O=S(=O)(Nc1nc(Cl)cnc1Br)c1ccc(Cl)s1 | null | null | null |
828,787 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:1... | CCOC(=O)Cc1ccc(O[C@H]2CCN(C(=O)OC(C)(C)C)C2)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 750 mg of ethyl 2-[4-[(3S)-1-(t-butoxycarbonyl)-3-pyrrolidyloxy]phenyl]acetate was dissolved in 10 ml of ethanol. 4 ml of 1 N aqueous sodium hydroxide solution was added to the obtained solution. After stirring at room temperature overnight, the solvent was evaporated. 1 N hydrochloric acid was added to the residue. Af... | CC(C)(C)OC(=O)N1CC[C@H](Oc2ccc(CC(=O)O)cc2)C1 | null | null | null |
172,393 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | O[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[CH:3]([NH:6][C:7]([O:9]CC)=[O:8])CO.[K].C([O-])(=[O:25])CCC>C1(C)C=CC=CC=1>[CH3:19][S:18][C:15]1[CH:14]=[CH:13][C:12]([CH:2]2[O:9][C:7](=[O:8])[NH:6][CH:3]2[OH:25])=[CH:17][CH:16]=1 | CCCC(=O)[O-] | CCOC(=O)NC(CO)C(O)c1ccc(SC)cc1 | null | [K] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | Compound (F) (5 g; 17.5 mmols) has been dissolved in warm toluene (25 ml). To this solution, an equimolar amount of potassium ter.butyrate has been added and the reaction mixture has been refluxed for 3 hours. Afterwards, almost all the solvent has been evaporated; water and ice have been added to the residue and the p... | CSc1ccc(C2OC(=O)NC2O)cc1 | null | null | null |
1,313,729 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1 | O=[N+]([O-])c1ccc(O)cc1 | CN(C)CCCl | null | Cl | O=C([O-])[O-] | [K+] | 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 mixture of 4-nitrophenol (3.5 g, 25 mmol), 2-(dimethylamino)ethyl chloride hydrochloride (3.6 g, 25 mmol), and potassium carbonate (13.2 g, 125 mmol) in acetone (100 mL) was heated to reflux for 30 hours. The solvent was removed under vacuum. The residue was partitioned between water (150 mL) and ethyl acetate (150 m... | CN(C)CCOc1ccc([N+](=O)[O-])cc1 | null | 57 | null |
796,434 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][NH:10][S:9]2(=[O:15])=[O:14])=[CH:5][CH:4]=1.[I:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[I:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][N:10]... | OCc1cccc(I)c1 | COc1ccc(CN2C(=O)CNS2(=O)=O)cc1 | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of the title B compound, 2-(4-methoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (1.02 g, 3.98 mmol), 3-iodo-benzyl alcohol (1.01 mL, 7.95 mmol) and triphenylphosphine (2.10 g, 8.0 mmol) in THF (50 mL) is cooled to 5° C. and treated with a solution of diethyl azodicarboxylate (1.26 mL, 8.0 mmol) in THF (10 ... | COc1ccc(CN2C(=O)CN(Cc3cccc(I)c3)S2(=O)=O)cc1 | null | null | null |
992,153 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.BrCCCN1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2C1=O>>[CH2:31]([O:32][C:16]([NH:15][CH2:14][CH2:10][CH2:9][O:1][C:2]1[CH:3]=[C:4]([C:8]2[C... | O=C1c2ccccc2C(=O)N1CCCBr | CC(C)(C)OC(=O)NCc1cccc(-c2cccc(O)c2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a similar manner to that described in Reference Example 31 using tert-butyl N-(3′-hydroxybiphenyl-3-ylmethyl)carbamate instead of tert-butyl N-(3′-hydroxybiphenyl-4-ylmethyl)carbamate and N-(3-bromopropyl)phthalimide instead of N-(4-bromobutyl)phthalimide. | CC(C)(C)OC(=O)NCc1cccc(-c2cccc(OCCCNC(=O)OCc3ccccc3)c2)c1 | null | null | null |
776,437 | ord_dataset-bf316bf78f4f45d4b275959c08104b7c | null | 2007-01-01T00:06:00 | true | [OH:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]([CH3:25])=[CH:9][C:10]([NH:16][C:17](=[O:24])[CH2:18][C:19]([O:21]CC)=[O:20])=[C:11]3[C:15]=2[CH2:14][CH2:13][CH2:12]3)=[CH:4][C:3]=1[CH2:28][CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[OH-].[Na+]>CO>[OH:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]([CH3:25])=[CH:9]... | CCOC(=O)CC(=O)Nc1cc(C)c(Oc2ccc(O)c(CC3CCOCC3)c2)c2c1CCC2 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | To ethyl N-{7-[4-hydroxy-3-(tetrahydropyran-4-ylmethyl)phenoxy]-6-methylindan-4-yl}malonamate (50 mg) were added methanol (10 mL) and a 1 mol/L aqueous solution of sodium hydroxide (8 mL), and the mixture was stirred under an argon atmosphere at 50° C. for 30 min. Adding water (20 mL), the reaction mixture was washed w... | Cc1cc(NC(=O)CC(=O)O)c2c(c1Oc1ccc(O)c(CC3CCOCC3)c1)CCC2 | null | 95.7 | null |
431,507 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | C([Li])CCC.C[Si](C)(C)[NH:8][Si](C)(C)C.[C:15]([C:17]1[CH:37]=[CH:36][C:20]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1)#[N:16].Cl>C1COCC1>[C:15]([C:17]1[CH:37]=[CH:36][C:20]([C:21]([N:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][... | C[Si](C)(C)N[Si](C)(C)C | CCOC(=O)CCN1CCN(C(=O)c2ccc(C#N)cc2)CC1 | null | Cl | [Li]CCCC | 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 solution of Li--N(Si(CH3)3)2 in 20 ml of THF, freshly prepared from C4H9Li and 1.13 g of hexamethyldisilazane, is added dropwise at -78°, with stirring, to a solution of 3.15 g of ethyl 3-(4-(4-cyanobenzoyl)piperazin-1-yl)propionate (FAB 316; obtainable by reacting 4-cyanobenzoyl chloride with ethyl piperazin-1-ylpro... | CCOC(=O)CCN1CCN(C(=O)c2ccc(C(=N)N)cc2)CC1 | null | null | null |
826,297 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | [OH:1][CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1([CH2:12][CH2:13][CH3:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(Cl)Cl.[CH3:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>N1C=CC=CC=1>[CH2:12]([C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][CH:2]1[O:1][C:21](=[O:22])[C:20]1[CH:24]=[CH:25][CH:26]... | Cc1ccccc1C(=O)Cl | CCCC1(C(=O)OCC)CCCC1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | null | 12 | Ethyl 2-hydroxy-1-n-propyl-cyclopentane carboxylate (6.00 g) was diluted using 60 ml of methylene chloride. At room temperature and with magnetic stirring, pyridine (3.66 ml) was slowly added, then 2-methyl-benzoyl chloride (5.95 ml) was dropwise added. Upon the completion of the addition, the reaction was continued fo... | CCCC1(C(=O)OCC)CCCC1OC(=O)c1ccccc1C | null | null | null |
1,709,255 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [H][H].[O:3]=[C:4]1[CH:9]([N:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:21]C=O)[N:12]=[C:11]2[CH3:24])[CH2:8][CH2:7][C:6](=[O:25])[NH:5]1>C(O)=O>[NH2:21][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:19](=[O:20])[N:10]([CH:9]1[CH2:8][CH2:7][C:6](=[O:25])[NH:5][C:4]1=[O:3])[C:11]([CH3:24])=[N:1... | [H][H] | Cc1nc2cccc(NC=O)c2c(=O)n1C1CCC(=O)NC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | null | null | In certain embodiments, when the hydrogen donor is formic acid, the transfer hydrogenation further comprises the step of hydrolyzing N-(3-(2,6-dioxopiperidin-3-yl)-2-methyl-4-oxo-3,4-dihydroquinazolin-5-yl)formamide to form 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione as described herein elsewhere. | Cc1nc2cccc(N)c2c(=O)n1C1CCC(=O)NC1=O | null | null | null |
1,736,794 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][CH:3]=1.CI.[C:12](=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:12])=[CH:4][CH:3]=1 | O=C([O-])[O-] | Cc1nc(Br)ccc1O | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | CC#N | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 6-bromo-2-methyl-pyridin-3-ol (4.06 g, 21.59 mmol), methyl iodide (1.61 mL, 25.91 mmol), potassium carbonate (5.97 g, 43.18 mmol) and acetonitrile (183.0 mL) was heated at reflux for 17 hours. The mixture was cooled to room temperature, filtered through a plug of celite and the solvent was evaporated under... | COc1ccc(Br)nc1C | null | 72.9 | null |
1,230,449 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | C[O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:18][C@H:17]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])[C@@H:16]([OH:24])[C@H:15]2[OH:25])=[C:7]([NH:26][CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:6]=1)=O.[CH2:41]([NH2:44])[CH2:42]... | CCC(=O)N[C@H]1C[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O | NCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 105 | 0.75 | 9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (62 mg, 1.0 mmol) is dissolved in ethylene diamine (3.4 ml, 51 mmol) and the solution is stirred at 105° C. The reaction is shown to be complete by LCMS after 45 minutes. The reaction mixtur... | CCC(=O)N[C@H]1C[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O | null | null | null |
1,371,582 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH2:1]([O:3][C:4]([C:6]([C:9]1[N:10](C(OC(C)(C)C)=O)[C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:8])[CH3:7])=[O:5])[CH3:2]>ClCCl.C(O)(C(F)(F)F)=O>[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[C:9]1[C:6]([CH3:7])([CH3:8])[C:4]([O:3][CH2:1][CH3:2])=[O:5] | CCOC(=O)C(C)(C)c1cc2ccccc2n1C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 5 | tert-Butyl 2-(2-(ethoxycarbonyl)propan-2-yl)-1H-indole-1-carboxylate (22.9 g, 69.1 mmol) was dissolved in dichloromethane (200 mL) before TFA (70 mL) was added. The mixture was stirred for 5 h at room temperature. The mixture was evaporated to dryness, taken up in dichloromethane and washed with saturated sodium bicarb... | CCOC(=O)C(C)(C)c1cc2ccccc2[nH]1 | null | 78.2 | null |
423,231 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2] | CC(C)(C)OC(=O)N1CCC(CCBr)CC1 | null | 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 | null | 3 | A solution of 4(2-bromo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (81.5 g 0.279 mol) in dry tetrahydrofuran (1000 ml) under nitrogen at 20° was treated portionwise, over 30 min, with potassium tert-butoxide (63.2 g 0.563 mol). The mixture was stirred at 25° for 3 h and partitioned between saturated aqueous a... | C=CC1CCN(C(=O)OC(C)(C)C)CC1 | null | 63.1 | null |
164,443 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [NH2:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][N:4]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:3]1=[O:22].Br[CH:24]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:25]([O:27][CH2:28][CH3:29])=[O:26]>>[CH2:28]([O:27][C:25]([CH:24]([NH:1][CH:2]1[CH2... | CCOC(=O)C(Br)CCc1ccccc1 | CC(C)(C)OC(=O)CN1CC(c2cccs2)SCC(N)C1=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 | Following the procedure described in Example 42(h), 0.40 g of t-butyl α-[6-amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (g) above] was N-alkylated using 0.64 g of ethyl 2-bromo-4-phenylbutyrate. The resulting product was subjected to silica gel column chromatography eluted... | CCOC(=O)C(CCc1ccccc1)NC1CSC(c2cccs2)CN(CC(=O)OC(C)(C)C)C1=O | null | null | null |
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