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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,555,906 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Br:1][C:2]1[C:7]([O:8][CH2:9][C@@H:10]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]2[O:23][CH:24]([C:31]([F:34])([F:33])[F:32])[C:25]3[C:30]([C:4]=2[CH:3]=1)=[CH:29][CH:28]=[N:27][CH:26]=3.C(O)(C(F)(F)F)=O>ClCCl>[Br:1][C:2]1[C:7]([O:8][CH2:9][C@@H:10]([NH2:15])[CH2:11][CH:12]([CH3:14])[CH3:13])... | CC(C)C[C@@H](COc1cc2c(cc1Br)-c1ccncc1C(C(F)(F)F)O2)NC(=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 | null | 8 | To a stirred solution of tert-butyl ((2S)-1-((9-bromo-5-(trifluoromethyl)-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (50 mg, 0.092 mmol) in dichloromethane (10 mL) at room temperature was added TFA (0.035 mL, 0.458 mmol) and stirred overnight. The solvent was removed under reduced pressure to aff... | CC(C)C[C@H](N)COc1cc2c(cc1Br)-c1ccncc1C(C(F)(F)F)O2 | null | 35.9 | null |
1,598,130 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH3:1][C:2]([CH3:37])([CH2:6][CH2:7][C:8](=[O:36])[N:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[O:23][C:24](=[O:35])[C:25]3[C:30]4[CH2:31][CH2:32][CH2:33][CH2:34][C:29]=4[S:28][C:26]=3[N:27]=2)[CH:17]=1)[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:3]([OH:5])=[O:4].[CH3:38]N(C=O)C.CI.C(=O)([O-])[O-].[K+].[... | CCC(CC)N(Cc1cccc(-c2nc3sc4c(c3c(=O)o2)CCCC4)c1)C(=O)CCC(C)(C)C(=O)O | CN(C)C=O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a mixture of 4.81 g of 2,2-dimethyl-5-oxo-5-{[3-(4-oxo-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-2-yl)benzyl](pentan-3-yl)amino}pentanoic acid and 50 mL of DMF were added 2.59 g of methyl iodide and 3.16 g of potassium carbonate, followed by stirring for 1 hour at room temperature. Water was added to a ... | CCC(CC)N(Cc1cccc(-c2nc3sc4c(c3c(=O)o2)CCCC4)c1)C(=O)CCC(C)(C)C(=O)OC | null | null | null |
1,275,270 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Br[C:2]1[CH:3]=[C:4]([NH:14][C:15]([C:17]2[N:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[CH2:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[CH3:24]>>[CH2:23]([C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[C:4]([NH:14][C:15]([C:17]3[N:18]=[N:19][CH:20]=[... | CCc1ccc(B(O)O)cc1 | O=C(Nc1cnc(OCC(F)(F)F)c(Br)c1)c1cccnn1 | null | null | null | null | null | null | null | 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 synthesized in analogy to Example 39, using pyridazine-3-carboxylic acid[5-bromo-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-amide (example 62 a) and B-(4-ethylphenyl)-boronic acid (CAN 63139-21-9) as starting materials; LC-MS (UV peak area/ESI) 98.9%, 403.1386 (M+H)+. | CCc1ccc(-c2cc(NC(=O)c3cccnn3)cnc2OCC(F)(F)F)cc1 | null | null | null |
1,607,139 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([CH2:11][C:12]([OH:14])=O)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[NH2:20][C:21]1[C:30]([Cl:31])=[CH:29][C:28]([C:32]([NH:34][NH2:35])=O)=[C:27]2[C:22]=1[CH2:23][CH2:24][CH2:25][O:26]2>>[Cl:31][C:30]1[C:21]([NH2:20])=[C:22]2[C:27](=[C:28]([C:32]3[O:14][C:12]([CH2:11][C... | NNC(=O)c1cc(Cl)c(N)c2c1OCCC2 | O=C(O)CC1CCN(C2CCC2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To the (1-cyclobutyl piperidin-4-yl) acetic acid (725 mg, 3.52 mmol, obtained in preparation 4) was added phosphoryl chloride (4 mL). The mixture was stirred for 15 minutes and 5-Amino-6-chloro-chroman-8-carboxylic acid hydrazide (500 mg, 2.0 mmol) was added. The reaction mixture was gradually heated to reflux for 30 m... | Nc1c(Cl)cc(-c2nnc(CC3CCN(C4CCC4)CC3)o2)c2c1CCCO2 | null | 31 | null |
591,931 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][C@H:14]1[CH2:28][O:27][C:17]2[CH:18]=[CH:19][C:20]3[C:21](=[O:26])[CH:22]=[CH:23][O:24][C:25]=3[C:16]=2[O:15]1.O>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH:14]2[CH2:28][O:27][C:17]3[CH:18]=[CH:19][C:20]4... | Cc1ccc(S(=O)(=O)Cl)cc1 | O=c1ccoc2c3c(ccc12)OC[C@H](CO)O3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 25 | 8 | p-Toluenesulfonyl chloride (0.60 g, 3.15 mmole) was added to solution of (2S)-2-(hydroxymethyl)-2,3-dihydro-7H-[1,4]dioxino[2,3-h]chromen-7-one (0.41 g, 1.75 mmole) in 50 mL of pyridine. The solution was stirred at room temperature overnight under nitrogen. Water was added to quench the excess tosyl chloride and the so... | Cc1ccc(S(=O)(=O)OCC2COc3ccc4c(=O)ccoc4c3O2)cc1 | null | null | null |
955,271 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [NH2:1][C:2]1[C:3]([C:24](N(OC)C)=[O:25])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH:9]=2)=[CH:6][N:7]=1>C1COCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[C:14]([NH:16][CH2:17][C:18]2[CH:19]=[CH:20][C... | CON(C)C(=O)c1nc(-c2cccc(C(=O)NCc3ccccc3)c2)cnc1N | null | 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 | 0 | 1 | A solution of 3-amino-6-{3-[(benzylamino)carbonyl]phenyl}-N-methoxy-N-methylpyrazine-2-carboxamide (2.5 g, 6.4 mmol) in THF (20 mL) was cooled to 0° C. Under N2 lithium aluminum hydride (0.364g, 9.58 mmol) was added and the reaction was stirred at 0° C. for 1 h. The mixture was then quenched with H2O at 0° C. Removal o... | Nc1ncc(-c2cccc(C(=O)NCc3ccccc3)c2)nc1C=O | null | 89.3 | null |
1,487,667 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([S:12](Cl)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([S:12]([NH:19][CH:16]2[CH2:18][CH2:17]2)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1 | NC1CC1 | O=S(=O)(Cl)c1cc(Br)cc(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride (0.2 g, 0.62 mmol) is added to a solution of cyclopropylamine (0.09 μl, 1.3 mmol) in DCM (5 ml), and the resulting solution is stirred at room temperature overnight. The reaction mixture is diluted with DCM (2×10 ml), washed with 0.1M HCl (5 ml), sat. aq. NaHCO3 (5 ml... | O=S(=O)(NC1CC1)c1cc(Br)cc(C(F)(F)F)c1 | null | null | null |
1,588,039 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([C@H:10]([NH:12][C:13]2[C:22]3[C:17](=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][N:14]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO>[NH2:1][C:4]1[CH:5]=[C:6]([C@H:10]([NH:12][C:13]2[C:22]3[C:17](=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15]... | C[C@@H](Nc1ncnc2c(C(N)=O)cccc12)c1cccc([N+](=O)[O-])c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 3 | A suspension of 4-{[(1R)-1-(3-nitrophenyl)ethyl]amino}quinazoline-8-carboxamide (1.50 g, 4.45 mmol) in methanol (125 mL) was shaken for 3 h in a | C[C@@H](Nc1ncnc2c(C(N)=O)cccc12)c1cccc(N)c1 | null | null | null |
1,465,168 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | Br[CH:2]([CH2:7][CH2:8]Br)[C:3]([O:5][CH3:6])=[O:4].[CH3:10][C:11]1([CH3:18])[CH2:16][CH:15]([NH2:17])[CH2:14][CH2:13][O:12]1>>[CH3:10][C:11]1([CH3:18])[CH2:16][CH:15]([N:17]2[CH2:8][CH2:7][CH:2]2[C:3]([O:5][CH3:6])=[O:4])[CH2:14][CH2:13][O:12]1 | CC1(C)CC(N)CCO1 | COC(=O)C(Br)CCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The reaction of methyl 2,4-dibromobutanoate 17 with 2,2-dimethyltetrahydro-2H-pyran-4-amine 18H yielded methyl 1-(2,2-dimethyltetrahydro-2H-pyran-4-yl)azetidine-2-carboxylate as a light brown solid (33%). MS ISP (m/e): 228.3 (100) [(M+H)]+. | COC(=O)C1CCN1C1CCOC(C)(C)C1 | null | 33 | null |
871,328 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | I[C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[CH:4][N:3]=1.[CH2:16]([OH:21])[CH:17]=[CH:18][C:19]#[CH:20]>C(#N)C.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:8][C:7]1[C:2]([C:20]#[C:19]/[CH:18]=[CH:17]/[CH2:1... | Nc1c(I)ncnc1Oc1ccccc1 | C#CC=CCO | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | [Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 4-Iodo-6-phenoxypyrimidin-5-amine (3.5 g) was dissolved in a mixed solvent of acetonitrile (185 mL)/triethylamine (136 mL), and 2-penten-4-yn-1-ol (1.1 g), trans-dichlorobis(triphenylphosphine)palladium(II) (392 mg) and copper(I) iodide (127 mg) were sequentially added. The title compound (1.79 g) was obtained as a pow... | Nc1c(C#C/C=C/CO)ncnc1Oc1ccccc1 | null | 59.9 | null |
1,574,178 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [OH:1][C@@H:2]1[CH2:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[C@@H:5]([C:12](=[O:14])[CH3:13])[C:4]([CH3:15])=[CH:3]1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C([O-])(=O)C.[Na+]>[OH-].[Na+]>[C:16]([O:1][C@H:2]1[CH:3]=[C:4]([CH3:15])[C@H:5]([C:12](=[O:14])[CH3:13])[C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:11]1)(=[O:18])[CH3:17... | CC(=O)OC(C)=O | CC(=O)[C@H]1C(C)=C[C@H](O)CC12CCCC2 | null | CC(=O)[O-] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 80 | 1 | A mixture of 8:92 cis/trans-1-(9-hydroxy-7-methylspiro[4.5]dec-7-en-6-yl)ethanone (4.2 g, 20.2 mmol) was treated with acetic anhydride (4 ml, 42.3 mmol) and sodium acetate (1.65 g, 20.2 mmol). The resulting mixture was stirred at 80° C. for 1 h, poured into cold 2N aqueous NaOH (50 ml), and extracted twice with MTBE (4... | CC(=O)O[C@H]1C=C(C)[C@H](C(C)=O)C2(CCCC2)C1 | null | 81.1 | null |
255,406 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [NH2:1][C@@H:2]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([NH:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][C:7]=1[F:14])=[O:4].[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([NH:28][C:29]([NH:1][C@@H:2]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3](... | O=C=Nc1ccccc1 | N[C@@H](Cc1ccccc1)C(=O)Nc1c(F)cc(F)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of Example 58 only using the product of Example 50 and phenylisocyanate, the title compound was obtained, mp 225°-233° C. | O=C(Nc1ccccc1)N[C@@H](Cc1ccccc1)C(=O)Nc1c(F)cc(F)cc1F | null | null | null |
1,035,410 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [N+](=[CH:3]P(=O)(OC)OC)=[N-].CC(C)([O-])C.[K+].[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:25]=O)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:28]1([CH2:27][C@H:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[C:25]#[CH:3])[CH:33]=[CH:32][CH:31]=... | CC(C)(C)OC(=O)N[C@H](C=O)Cc1ccccc1 | COP(=O)(C=[N+]=[N-])OC | 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 | -35 | 0.25 | To a solution of dimethyl diazomethylphosphonate (0.60 g, 4.0 mmol) (prepared as described by Brown, D. et al., J. Org. Chem. 1996, 61(7), 2540-1 which is hereby incorporated by reference in its entirety and for all purposes as if specifically set forth herein) in 20 mL of THF at −78° C. was added potassium tert-butoxi... | C#C[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C | null | 36.7 | null |
833,757 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[CH:5][C:6]2[C:12]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])=[N:11][CH2:10][C:9](=[O:21])[NH:8][C:7]=2[CH:22]=1.[CH2:31](I)[CH2:32][CH3:33]>>[CH3:1][O:2][C:3]1[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29... | COc1ccccc1-c1cc2c(cc1OC)NC(=O)CN=C2c1cccc(C#N)c1 | CCCI | null | null | null | null | null | null | null | 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 from 3-[8-methoxy-7-(2-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile Example 10 using the same method described for Example 35 using propyl iodide instead of hexyl bromine. The title compound (99 mg) was obtained as a white solid, yield=89%. | CCCN1C(=O)CN=C(c2cccc(C#N)c2)c2cc(-c3ccccc3OC)c(OC)cc21 | null | 89 | null |
426,000 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | [Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:9])[CH2:6][CH2:7][CH3:8].[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:5](=[O:9])[CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=1 | CCCC(=O)Cl | Fc1ccccc1 | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | Aluminum chloride (139 g, 1.04 mol) was added to a solution of butyryl chloride (55.45 g, 0.520 mol, Aldrich) in dichloromethane (500 ml) stirring under a nitrogen atmosphere at 25° C. A solution of fluorobenzene (50.1 g, 0.521 mol, Aldrich) in dichloromethane was added and stirring was continued for 18 h. The reaction... | CCCC(=O)c1ccc(F)cc1 | null | 80.2 | null |
570,422 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | O1CCCCC1[O:7][CH2:8][CH2:9][O:10][N:11]=[C:12]1[C:16](=[O:17])[C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[O:13]1>CO>[OH:7][CH2:8][CH2:9][O:10][N:11]=[C:12]1[C:16](=[O:17])[C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[O:13]1 | O=C1C(=NOCCOC2CCCCO2)Oc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 2.07 g (0.01 mol) of benzofuran-2,3-dione2-{O-[2-(tetrahydropyran-2-yloxy)-ethyl]oxime} (XIV-2) are dissolved in 12 ml of methanol and stirred at room temperature with 100 mg of acidic ion exchanger resin for 16 hours. 40 ml of methanol are added to the reaction mixture which is then warned until the crystals have diss... | O=C1C(=NOCCO)Oc2ccccc21 | null | 81.6 | null |
623,421 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@H:5]([NH2:11])[CH2:4]2.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1/[CH:17]=[CH:18]/[C:19](O)=[O:20]>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@H:5]([NH:11][C:19](=[O:20])/[CH:18]=[CH:17]/[C:13]1[O:12][CH:16]=[CH:15][CH:14]=1)[CH2:4]2 | O=C(O)/C=C/c1ccco1 | N[C@@H]1CN2CCC1CC2 | 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 | Prepared as a free base by a method analogous to that described in Example 1 from (S)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride and E-3-(2-furyl)propenoic acid; the compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent, followed by recrystallization fro... | O=C(/C=C/c1ccco1)N[C@@H]1CN2CCC1CC2 | null | null | null |
1,076,814 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:56]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH2:57][C:58](O)=... | CC(C)(C)OC(=O)NCC(=O)O | O=C(OCc1ccccc1)N1CC[C@H](NC2CCCCC2)C1 | 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 | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of (3S)-1-Cbz-3-{cyclohexylamino}pyrrolidine (3.0 g, 10.0 mmol), prepared in Intermediate 2, in DMF (30 mL) were added DIPEA (3.50 mL, 20.0 mmol), HBTU (4.88 g, 13 mmol), BOC-Gly (1.92 g, 11 mmol). After the mixture was stirred at rt for 4 h, the solvent was removed in vacuo, and the residue was diluted w... | CC(C)(C)OC(=O)NCC(=O)N(C1CCCCC1)[C@H]1CCN(C(=O)OCc2ccccc2)C1 | null | 100.7 | null |
1,249,834 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | C[O:2][C:3](=[O:42])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=3[F:25])[C@:16]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[F:35])([C:26]#[N:27])[C@H:15]([CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[NH:14]2)=[O:12])=[CH:6][C:5]=1[Cl:41].[OH-].[Na... | COC(=O)c1ccc(NC(=O)[C@@H]2N[C@@H](CC(C)(C)C)[C@](C#N)(c3ccc(Cl)cc3F)[C@H]2c2cccc(Cl)c2F)cc1Cl | 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 | 55 | 1 | rac 4-{[(2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-2-chloro-benzoic acid methyl ester (54 mg) was dissolved in MeOH (10 mL) with help of slight heating. To the stirred solution was added NaOH (1N, 2 mL) and the mixture was stirr... | CC(C)(C)C[C@@H]1N[C@@H](C(=O)Nc2ccc(C(=O)O)c(Cl)c2)[C@H](c2cccc(Cl)c2F)[C@@]1(C#N)c1ccc(Cl)cc1F | null | null | null |
838,939 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | C([O:8][C:9]1[CH:24]=[C:23]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.CO>[C].[Pd].O1CCCC1>[OH:8][C:9]1[CH:24]=[C:23]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:22]=[CH:21][C:10]=1[C:11](... | CC1(C)OB(c2ccc(C(=O)OCc3ccccc3)c(OCc3ccccc3)c2)OC1(C)C | null | null | [Pd] | 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 | 25 | 3 | To a mixture of benzyl 2-benzyloxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.24 g), methanol (6 mL) and tetrahydrofuran (6 mL) was added 10% palladium-carbon (0.05 g) at room temperature under an atmosphere of argon. The mixture was stirred at room temperature for 3 hrs under an atmosphere of hydrogen.... | CC1(C)OB(c2ccc(C(=O)O)c(O)c2)OC1(C)C | null | 102.4 | null |
3,074 | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | null | 1976-01-01T00:03:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[CH:20]=[CH:19][N:18]=[C:17]2[CH2:21]O)=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[F:1][C:2]1[CH:3]=[CH... | O=C1NC(=O)c2ccccc21 | O=C(c1ccccc1)c1cc(F)ccc1-n1ccnc1CO | 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 | null | null | null | null | null | null | null | null | null | null | null | null | null | In the manner given in Example 17, 5-fluoro-2-[2-(hydroxymethyl)imidazol-1-yl]benzophenone is treated with phthalimide and triphenylphosphine and finally with diethyl azodicarboxylate to give 5-fluoro-2-[2-(phthalimidomethyl)imidazol-1-yl]benzophenone. | O=C(c1ccccc1)c1cc(F)ccc1-n1ccnc1CN1C(=O)c2ccccc2C1=O | null | null | null |
12,517 | ord_dataset-a0071d97083e4e69ae8872417ed2776b | null | 1976-01-01T00:09:00 | true | BrC(C)C([C:5]1[CH:15]=[CH:14][C:8]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:7][CH:6]=1)=O.C(#N)C.[ClH:20]>CC(=O)CC>[ClH:20].[CH3:13][S:10]([NH:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:15][CH:14]=1)(=[O:12])=[O:11] | CC(Br)C(=O)c1ccc(NS(C)(=O)=O)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4'-(2-bromopropionyl)methanesulfonanilide (15.3 g., 0.05 mole) and α,60 -dimethylphenethylamine (16.42 g., 0.11 mole) in 200 ml. of acetonitrile is refluxed for a period of 16 hr. The product is isolated by concentrating the reaction mixture under reduced pressure, dissolving the residue in chloroform whic... | CS(=O)(=O)Nc1ccccc1 | null | null | null |
250,830 | ord_dataset-41ea179beba54bed8cd874a5ec3469f7 | null | 1992-01-01T00:07:00 | true | Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].O=[C:10]([CH3:18])[CH2:11][CH2:12][C:13](OCC)=[O:14]>O>[O:5]=[C:4]1[CH2:3][N:2]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]2([CH3:18])[NH:6]1 | CCOC(=O)CCC(C)=O | NCC(N)=O | null | Cl | [Na+] | [OH-] | 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 | To a solution of glycinamide hydrochloride (18.4 g, 0.166 mol) in water (200 ml), adjusted to pH 9.5 with 10% sodium hydroxide (about 60 ml), ethyl 4-oxopentanoate (20 g, 0.139 mol) was added. The solution was refluxed for 24 hours. After cooling the solvent was evaporated under vacuum and the residue was chromatograph... | CC12CCC(=O)N1CC(=O)N2 | null | 21 | null |
835,598 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [N:1]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14](OC)=[O:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3].CC(C[AlH]CC(C)C)C>C1COCC1>[N:1]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][OH:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3] | COC(=O)c1ccc2c(c1)OCC[C@H]2N=[N+]=[N-] | 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 | 2.5 | (R)-Methyl 4-azido-3,4-dihydro-2H-chromene-7-carboxylate (21.50 mmol, 1.0 eq) in 50 mL THF was cooled to 0° C., and treated with DIBAL (63.0 mmol, 3.0 eq). After 2.5 h, the reaction mixture was quenched by adding 50% saturated K—Na tartrate (60 mL). After stirring 1 h at room temperature, the solution was extracted wit... | [N-]=[N+]=N[C@@H]1CCOc2cc(CO)ccc21 | null | null | null |
145,415 | ord_dataset-d6cdba90760a47779a36ece5962905eb | null | 1986-01-01T00:06:00 | true | [OH-:1].[Na+].Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][C:5]=1[C:16]([F:19])([F:18])[F:17].Cl>>[F:17][C:16]([F:19])([F:18])[C:5]1[CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=1[OH:1] | O=[N+]([O-])c1cc([N+](=O)[O-])c(Cl)c(C(F)(F)F)c1 | [OH-] | null | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 60 | null | To a 1000 cm3 flask equipped with a stirrer, dropping funnel, reflux and thermometer 300 g /0.75 mole/ of a 10% by weight NaOH solution are added 81.3 g /0.3 mole/ of 2-chloro-3,5-dinitro-benzotrifluoride of a purity of 95% are added under stirring. The temperature is raised to 60° C. and the reaction mixture is stirre... | O=[N+]([O-])c1cc([N+](=O)[O-])c(O)c(C(F)(F)F)c1 | null | 90 | null |
1,394,085 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)=[C:11]=[O:12]>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]([NH:10][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)=[O:12])=[C:4]([F:9])[CH:3]=1 | Nc1ccc(Br)cc1F | Cc1cccc(N=C=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | A 0° C. solution of 4-bromo-2-fluoroaniline (1 g, 5.26 mmol) in dichloromethane (10 mL) was treated dropwise with 1-isocyanato-3-methylbenzene (0.71 mL, 5.26 mmol), warmed to room temperature, stirred for 18 hours, and filtered. The filter cake was washed with dichloromethane and dried to provide 0.62 g of the desired ... | Cc1cccc(NC(=O)Nc2ccc(Br)cc2F)c1 | null | 36.5 | null |
90,817 | ord_dataset-6ba93916f2ad4247804469d8c2600b26 | null | 1982-01-01T00:01:00 | true | C([S:4][CH2:5][CH2:6][C:7]([N:9]1[CH2:16][C:15]([O:19][CH3:20])([O:17][CH3:18])[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=O)C.N>>[SH:4][CH2:5][CH2:6][C:7]([N:9]1[CH2:16][C:15]([O:19][CH3:20])([O:17][CH3:18])[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8] | COC1(OC)C[C@@H](C(=O)O)N(C(=O)CCSC(C)=O)C1 | null | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product from part (a) is hydrolyzed with concentrated ammonia according to the procedure of Example 4 to yield 1-(3-mercapto-1-oxopropyl)-4,4-dimethoxy-L-proline. | COC1(OC)C[C@@H](C(=O)O)N(C(=O)CCS)C1 | null | null | null |
1,644,555 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [CH:1]1([CH2:6][C:7]2[N:11]([CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:10]3[CH:17]=[CH:18][C:19]([C:21]([OH:23])=O)=[CH:20][C:9]=3[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C.C(Cl)(=O)C([Cl:32])=O>ClCCl>[CH:1]1([CH2:6][C:7]2[N:11]([CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:10]3[CH:17]=[CH:18][C:19]([C:21]([Cl:32]... | O=C(Cl)C(=O)Cl | CCC(CC)n1c(CC2CCCC2)nc2cc(C(=O)O)ccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 16 | To 8.00 g of 2-cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid in 100 ml of dichloromethane 0.1 ml of DMF and 4 ml of oxalyl chloride were added. The reaction was stirred at it for 16 h, then concentrated and co-distilled with toluene to obtain 8.45 g (100%) of the crude product as a brown soli... | CCC(CC)n1c(CC2CCCC2)nc2cc(C(=O)Cl)ccc21 | null | 100 | null |
1,459,812 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH3:12].CC(C)([O-])C.[K+].[I:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=1.CCOCC>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([I:19])[CH:21]=2)([CH3:9])[CH3:10])=[CH:4][C:3]=1[CH3:12] | Cc1cc(C(C)(C)N)ccc1Cl | Ic1cccc(I)c1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | CCOCC | null | null | null | null | null | null | null | null | null | 25 | null | A suspension of amine INT 22 (2.8 g, 15.24 mmol) and potassium tert-butoxide (5.99 g, 53.4 mmol) in DME (25 mL) was purged with argon for 5 minutes. Then, PEPPSI-IPr® (207 mg, 0.305 mmol) and 1,3-diiodobenzene (5.03 g, 15.24 mmol) were added and the flask was closed. The mixture was stirred at room temperature over the... | Cc1cc(C(C)(C)Nc2cccc(I)c2)ccc1Cl | null | null | null |
1,261,370 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [Br:1][C:2]1[C:3]([S:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH:5]=O.Cl.[NH2:19][OH:20]>C(O)(C)C.O>[Br:1][C:2]1[C:3]([S:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH:5]=[N:19][OH:20] | NO | CC(C)(C)Sc1c(Br)cc([N+](=O)[O-])cc1C=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | A solution of 3-bromo-2-tert-butylsulfanyl-5-nitro-benzaldehyde (1.2 g, 3.8 mmol) and hydroxylamine hydrochloride (1.2 g, 7.7 mmol) in isopropanol (36 mL) and water (8 mL) was heated to 90° C. for 16 h. The reaction mixture was cooled and concentrated to remove isopropanol. Water was added to the residue, followed by s... | CC(C)(C)Sc1c(Br)cc([N+](=O)[O-])cc1C=NO | null | 150.1 | null |
467,836 | ord_dataset-8cd3720738054d76b936f66e14d8cba6 | null | 2000-01-01T00:06:00 | true | Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][N:19]=2)(=[O:17])=[O:16])[C:3]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].[Na]>C(O)CO>[OH:27][CH2:28][CH2:29][O:34][C:2]1[N:7]=[C:6]([N:8]2[C... | COc1ccccc1Oc1c(Cl)nc(N2CCOCC2)nc1NS(=O)(=O)c1ccc(C(C)C)cn1 | null | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | OCCO | null | null | null | null | null | null | null | null | null | null | null | null | reacting the product of step d) with sodium in ethylene glycol to form 5-isopropyl-pyridine-2-sulfonic acid 6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl-amide, and | COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)C)cn2)nc(N2CCOCC2)nc1OCCO | null | null | null |
1,429,231 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [CH2:1]([N:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][C:6]1=[O:12])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:15])=O>CN(C=O)C>[Br:15][C:8]1[CH:9]=[CH:10][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6](=[O:12])[CH:7]=1 | CCCCn1ccc(O)cc1=O | O=P(Br)(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 110 | null | To a solution of intermediate D2 (1.44 g, 8.6 mmol) in DMF (140 ml) was added phosphorus oxybromide (5.4 g, 18.9 mmol) and the mixture was heated at 110° C. for 1 hour. After cooling in an ice bath the solution was partitioned between water and EtOAc. After three extractions with EtOAc the combined organic fractions we... | CCCCn1ccc(Br)cc1=O | null | 92 | null |
966,909 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CC(C)=O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH:5]=[CH:4][C:3]=1[C:9](=... | COc1ccc(CCl)cc1 | CC(=O)c1ccc(O)cc1O | null | O=C([O-])[O-] | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 16 | 2′,4′-Dihydroxyacetophenone (11.71 g, 0.077 mol), 4-methoxybenzyl chloride (10.44 ml, 0.077 mol), anhydrous potassium carbonate (11.75 g, 0.085 mol) and potassium iodide (12.78 g, 0.077 mol) are heated together in refluxing dry acetone (80 ml) for 4 hours. The mixture is then cooled to room temperature, poured into wat... | COc1ccc(COc2ccc(C(C)=O)c(O)c2)cc1 | null | null | null |
641,752 | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | null | 2004-01-01T00:07:00 | true | [C:1]([C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH2:17])=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6])#[N:2].[Cl:18][CH2:19][CH2:20][CH2:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]1[C:31](O)=[O:32]>>[C:1]([C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13]... | O=C(O)c1cc2ccccc2n1CCCCl | CC(C)C[C@@H](C#N)NC(=O)[C@@H]1CCCC[C@@H]1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (1R,2S)-2-Amino-cyclohexanecarboxylic acid ((S)-1-cyano-3-methyl-butyl)-amide was coupled with afford 1-(3-chloro-propyl)-1H-indole-2-carboxylic acid using the procedure of Example 11 to yield 1-(3-chloro-propyl)-1H-indole-2-carboxylic acid [(1S,2R)-2-((S)-1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide. | CC(C)C[C@@H](C#N)NC(=O)[C@@H]1CCCC[C@@H]1NC(=O)c1cc2ccccc2n1CCCCl | null | null | null |
1,620,939 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[N:12]1([CH:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:19][NH2:20])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:20][CH2:19][CH:18]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)... | O=C(O)c1cccc(Cl)c1Cl | NCC(c1ccccn1)N1CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | From 2,3-dichlorobenzoic acid and (2-morpholin-4-yl-2-pyridin-2-ylethyl)amine. | O=C(NCC(c1ccccn1)N1CCOCC1)c1cccc(Cl)c1Cl | null | null | null |
1,494,741 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [C:1]1([S:7][C:8]([S:11](F)(=[O:13])=[O:12])([F:10])[F:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>ClCCCl>[CH2:15]([NH:22][S:11]([C:8]([F:10])([F:9])[S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:13])=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1 | O=S(=O)(F)C(F)(F)Sc1ccccc1 | NCc1ccccc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | null | Added to a solution of 1,2-dichloroethane (15 ml), containing the PhSCF2SO2F (1.46 g, 5 mmol) obtained according to the method from example 7, was freshly distilled benzylamine (2.7 ml, 25 mmol). The mixture was stirred and heated at 50° C. for 20 h until the disappearance of PhSCF2SO2F (monitored by TLC and 19F NMR/CD... | O=S(=O)(NCc1ccccc1)C(F)(F)Sc1ccccc1 | null | null | null |
1,094,663 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([SH:11])[S:9][CH:10]=1)[CH3:2].[C:13]([O:17][C:18](=[O:22])[CH:19](Br)[CH3:20])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18](=[O:22])[CH:19]([S:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:12])[N:7]=1)[CH3:20])([CH3:16])([CH3:15])[CH3:14] | CCOC(=O)Cc1csc(S)n1 | CC(Br)C(=O)OC(C)(C)C | null | null | null | null | null | null | null | 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 obtained by an operation similar to that of Example 2 and using (2-mercapto-1,3-thiazol-4-yl)acetic acid ethyl ester synthesized in Example 1 and 2-bromopropionic acid tert-butyl ester to give 2-{[4-(2-ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester, followed by sequentia... | CCOC(=O)Cc1csc(SC(C)C(=O)OC(C)(C)C)n1 | null | null | null |
559,132 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [C:1]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][C:4]([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][N:13](C)[CH2:14]C2C=CC=CC=2)=[CH:3][CH:2]=1.[H][H].[ClH:36].Cl.CC(O)C>CO.[Pd]>[ClH:36].[ClH:36].[C:1]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:6... | [H][H] | CN(CCNCCC(c1ccccc1)c1ccc(-c2ccccc2)cc1)Cc1ccccc1 | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | A mixture of (±)-N-[3-([1,1′-biphenyl]-4-yl)-3-phenylpropyl]-N′-methyl-N′-(phenylmethyl)-1,2-ethanediamine (0.006 mol) in methanol (150 ml) was hydrogenated at room temperature with palladium on carbon (10%, 1 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was ... | CNCCNCCC(c1ccccc1)c1ccc(-c2ccccc2)cc1 | null | null | null |
1,493,617 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | FC(F)(F)C(O)=O.C(OC([NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([CH3:34])([S:30]([CH3:33])(=[O:32])=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:18][CH:17]=1)=O)(C)(C)C>>[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]([CH3:34])([S:30]([CH3:33])(=[O:32])=[O:31])[C:25]([O:27][CH2:28][CH3:2... | CCOC(=O)C(C)(CCc1ccc(NC(=O)OC(C)(C)C)cc1)S(C)(=O)=O | 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 | 2 | Trifluoroacetic acid (50 mL, 650 mmol) was added to a solution of (+/−)-ethyl 4-{4-[(tert-butoxycarbonyl)amino]phenyl}-2-methyl-2-(methylsulfonyl)butanoate (6.47 g, 16.2 mmol) in dicholoromethane (100 mL) at 0° C. The reaction was allowed to warm to room temperature and was stirred for 2 hours. The reaction was then co... | CCOC(=O)C(C)(CCc1ccc(N)cc1)S(C)(=O)=O | null | 72.6 | null |
71,876 | ord_dataset-520610070b3c4780a03b44c7fcecc28f | null | 1980-01-01T00:10:00 | true | [C:1]([C:3]([C:15]#[N:16])=[C:4]1[CH2:9][CH2:8][C:7](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[CH2:6][CH2:5]1)#[N:2]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH:5]1[C:4](=[C:3]([C:1]#[N:2])[C:15]#[N:16])[CH:9]=[CH:8][C:7](=[C:10]([C:11]#[N:12])[C:13]#[N:14])[CH:6]=1 | N#CC(C#N)=C1CCC(=C(C#N)C#N)CC1 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | According to the procedure of Fatiadi Synthesis, 1976, 133, incorporated herein by reference, the 1,4-bis(dicyanomethylene)cyclohexane is allowed to react with manganese dioxide in refluxing (110° C.) toluene for ca. 15 minutes to provide TCNQ in ca. 60% yields. | N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1 | null | null | null |
496,291 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH:2]1[O:4][CH2:3]1.[NH:14]1[CH:19]=[CH:18][CH:17]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1>>[N:5]1([CH2:1][CH:2]([OH:4])[CH2:3][N:14]2[CH2:15][CH:16]=[C:17]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C... | C1=CC(c2c[nH]c3ccccc23)CCN1 | c1ccc2c(c1)ccn2CC1CO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A methanolic solution of 1-N-glycidylindole (0.52 g, 3.0 mmole) from example 4 and 3-(4-tetrahydropyridinyl)indole (0.59 g, 3.0 mmole) was refluxed under nitrogen for 24 hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography (ethyl acetate) to afford the titled... | OC(CN1CC=C(c2c[nH]c3ccccc23)CC1)Cn1ccc2ccccc21 | null | 47.6 | null |
1,735,867 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:22][N:12]3[C:13](=[O:21])[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]3=[N:10][CH2:9]2)=[C:4]([CH3:23])[CH:3]=1.C(N(CC)CC)C.[C:31]1([CH3:40])[CH:36]=[CH:35][CH:34]=[C:33]([N:37]=[C:38]=[O:39])[CH:32]=1>C(Cl)Cl>[CH3:23][C:4]1[CH:3]=[C:2]([NH:1][C:38]([NH:37][C:33]... | Cc1cc(N)ccc1C1CN=C2c3ccccc3NC(=O)N2C1 | Cc1cccc(N=C=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | To a mixture of 3-(4-amino-2-methylphenyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,2-c]quinazolin-6-one (92 mg, 0.30 mmol) and triethylamine (0.125 mL, 0.90 mmol) in 2.5 mL CH2Cl2 at rt was added meta-tolyl isocyanate (0.057 mL, 0.45 mmol) and the reaction stirred at rt. After 2 hours, an additional 0.015 mL meta-tolyl isocya... | Cc1cccc(NC(=O)Nc2ccc(C3CN=C4c5ccccc5NC(=O)N4C3)c(C)c2)c1 | null | 75.1 | null |
589,414 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH2:16][CH2:17][F:18])[N:11]=[N:10]2)=[C:4]([F:19])[CH:3]=1.[N+:20]([O-])([OH:22])=[O:21]>>[Cl:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH2:16][CH2:17][F:18])[N:11]=[N:10]2)=[C:6]([N+:20]([O-:22])=[O:21])[C:7]=1[OH:... | O=[N+]([O-])O | O=c1n(CCCF)nnn1-c1cc(O)c(Cl)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | 1-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-(3-fluoropropyl)-tetrazolinone (2.91 g) was gradually added into an ice-cooled nitric acid (20 ml) and stirred for 30 minutes. Crushed ice was added followed by extraction with ethyl acetate. The ethyl acetate extract was washed with water, dried over sodium sulfate, concentrated... | O=c1n(CCCF)nnn1-c1c(F)cc(Cl)c(O)c1[N+](=O)[O-] | null | null | null |
1,270,351 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | COC1C=C(OC)C=CC=1C[NH:6][C:7]1[C:12]2[C:13](=[O:17])[N:14]([CH3:16])[CH2:15][C:11]=2[CH:10]=[CH:9][N:8]=1.[OH-].[Na+]>Cl>[NH2:6][C:7]1[C:12]2[C:13](=[O:17])[N:14]([CH3:16])[CH2:15][C:11]=2[CH:10]=[CH:9][N:8]=1 | COc1ccc(CNc2nccc3c2C(=O)N(C)C3)c(OC)c1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-[(2,4-dimethoxybenzyl)amino]-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one one (1.8 g, 5.7 mmol) in 37% HCl (7.0 mL) was stirred at rt for 16 hours. The reaction mixture was neutralized with NaOH and extracted with EtOAc (15 mL). The organic layer was washed with water (10 mL), washed with brine (... | CN1Cc2ccnc(N)c2C1=O | null | null | null |
1,655,139 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[N:14][C:13]=3[CH:30]=2)O1.Br[C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH2:39])=[O:38])=[C:35]([F:42])[CH:34]=1>>[C:37]([C:36]1[CH:40]=[CH:41][C:33]([C:9]2[CH:10]... | NC(=O)c1ccc(Br)cc1F | CC(C)(C)OC(=O)N1CCC(c2nc3cc(B4OC(C)(C)C(C)(C)O4)ccc3o2)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 | Following the General Procedure-3, the titled compound (25 mg) was prepared from Intermediate 8 (150 mg, 0.35 mmol) and 4-bromo-2-fluorobenzamide (77 mg, 0.35 mmol) as a white solid. M.P.: 202-206° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.22 (t, J 8.3, 1H), 7.89 (s, 1H), 7.59-7.49 (m, 3H), 7.37 (dd, J 1.6, 13.24, 1H), 6.... | CC(C)(C)OC(=O)N1CCC(c2nc3cc(-c4ccc(C(N)=O)c(F)c4)ccc3o2)CC1 | null | 16.3 | null |
1,317,808 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [CH3:1][NH:2][CH2:3][CH:4]1[O:9][C:8]2[CH:10]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=[CH:13][C:7]=2[CH2:6][O:5]1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CCOC(C)=O>[CH2:18]([N:2]([CH3:1])[CH2:3][CH:4]1[O:9][C:8]2[CH:10]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])... | BrCc1ccccc1 | CNCC1OCc2ccc(S(C)(=O)=O)cc2O1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | N-methyl-1-[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methanamine (1.05 g, 4.1 mmol), benzylbromide (0.49 ml, 4.1 mmol), potassium carbonate (0.68 g, 4.9 mmol) and ACN (20 ml) were heated at 50° C. for 12 h. EtOAc was added, the reaction mixture was filtered and concentrated. Purification by flash chromatography (isoo... | CN(Cc1ccccc1)CC1OCc2ccc(S(C)(=O)=O)cc2O1 | null | 63.9 | null |
1,276,328 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Br[C:2]1[CH:3]=[C:4]([N:22]([CH2:29][CH3:30])[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8].[CH:31]([C:33]1[N:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)=[O:32].C([O-])([O-])=O.[Na+].[Na+]>O1... | O=Cc1ccc(B(O)O)cn1 | CCN(c1cc(Br)cc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C)C1CCOCC1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 80 | null | To a stirred solution of 5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide (1 g, 2.15 mmol) and (6-formylpyridin-3-yl)boronic acid (0.539 g, 2.31 mmol) in dioxane/water mixture (15 mL+3 mL), Na2CO3 (0.82 g, 7.74 mmol) was added and solution purged ... | CCN(c1cc(-c2ccc(C=O)nc2)cc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C)C1CCOCC1 | null | 55.5 | null |
1,574,453 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].[OH:10][CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[N:5]1[CH:6]=[CH:7][CH:2]=[C:3]([CH2:8][O:9][C:17]2[C:12]([CH:11]=[O:10])=[CH:13][N:14]=[CH:15][CH:16]=2)[CH:4]=1 | O=Cc1cnccc1Cl | OCc1cccnc1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 4-chloro-3-pyridine aldehyde (1.0 g, 7 mmol, 1.0 eq), 3-hydroxymethylpyridine (5.4 g, 49.45 mmol, 7 eq) and p-toluenesulfonic acid mon hydrate (1.3 g, 7.0 mmol, 1.0 eq) in benzene (30 mL) were heated using a Dean-Stark trap for 24 h. Solvent was removed and purified by column chromatography to provide the alkylation pr... | O=Cc1cnccc1OCc1cccnc1 | null | null | null |
1,315,424 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)=[O:4] | COC(=O)C1CCCN1c1ccc([N+](=O)[O-])cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-(4-nitro-phenyl)-pyrrolidine-2-carboxylic acid methyl ester (0.55 g, 2.2 mmol) in methanol (15 ml) was hydrogenated over 10% Pd—C (50 mg) at 30 psi until no further gas uptake was observed. The reaction mixture was then filtered over celite and the filtrate evaporated to yield 1-(4-amino-phenyl)-pyrroli... | COC(=O)C1CCCN1c1ccc(N)cc1 | null | 72.2 | null |
1,389,735 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | F[C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[NH:13][CH:14]=[C:15]([CH2:19][C:20]3[CH:21]=[N:22][C:23]([O:26][CH3:27])=[N:24][CH:25]=3)[C:16](=[O:18])[N:17]=2)=[CH:6][C:3]=1[C:4]#[N:5].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=1[C:36]([F:39])([F:38])[F:37].C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[Cl... | Oc1ccc(Cl)c(C(F)(F)F)c1 | COc1ncc(Cc2c[nH]c(CCc3ccc(F)c(C#N)c3)nc2=O)cn1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a solution of 2-fluoro-5-[2-(5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-4-oxo-1,4-dihydro-2-pyrimidinyl)ethyl]benzonitrile (80 mg, 0.219 mmol) and 4-chloro-3-(trifluoromethyl)phenol (64.6 mg, 0.328 mmol) in NMP (2 mL), K2CO3 (60.5 mg, 0.438 mmol) was added. The reaction vessel was sealed and stirred at room temp for 10... | COc1ncc(Cc2c[nH]c(CCc3ccc(Oc4ccc(Cl)c(C(F)(F)F)c4)c(C#N)c3)nc2=O)cn1 | null | 25.3 | null |
31,260 | ord_dataset-56c07ce5503b46d1805bdf471f8f1c55 | null | 1977-01-01T00:10:00 | true | Cl[CH2:2][C:3]([C:5]1[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[F:18])[CH:7]=[CH:8][CH:9]=1)=[O:4].[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>CO>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:6]2[CH:7]=[CH:8][CH:9]=[C:5]2[C:3](=[O... | c1ccc(N2CCNCC2)cc1 | O=C(CCl)c1cccn1Cc1ccc(Cl)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CO | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-chloroacetyl-1-(4-chloro-2-fluorobenzyl)pyrrole, N-phenylpiperazine and triethylamine in methanol is treated by the procedure described in Example 1b to produce 1-(4-chloro-2-fluorobenzyl)-2-[α-(4-phenylpiperazino)acetyl]pyrrole. | O=C(CN1CCN(c2ccccc2)CC1)c1cccn1Cc1ccc(Cl)cc1F | null | null | null |
1,311,033 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([Cl:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[C:24]([N:31](C)[C:32]1[N:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:33]=1[CH3:47])(OC(C)(C)C)=O>>[Cl:21][C:16]1[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2](... | Cn1cc(-n2c(=O)n(C)c3cnc4ccc(Br)cc4c32)c(Cl)n1 | Cc1cc(B2OC(C)(C)C(C)(C)O2)cnc1N(C)C(=O)OC(C)(C)C | null | null | null | null | null | null | null | 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 synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(3-chloro-1-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate K) and 6-(N-boc-methylamino)-5-methylpyridine-3-boronic acid pinacol ester (Combi-Blocks, San Diego, USA, 58.8 mg, 0.176... | CNc1ncc(-c2ccc3ncc4c(c3c2)n(-c2cn(C)nc2Cl)c(=O)n4C)cc1C | null | null | null |
929,503 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[CH:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)=[O:21])=[CH:15][C:14]=1B1OC(C)(C)C(C)(C)O1>>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)=[O:21])=[CH:17][C:18]=1[C:... | Cc1noc2cc(Br)ccc12 | Cc1ccc(NC(=O)c2ccoc2)cc1B1OC(C)(C)C(C)(C)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Example 6 was prepared in a similar manner to Example 4 using 6-bromo-3-methyl-1,2-benzisoxazole (11 mg) and N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-furamide (Intermediate 17, 16 mg) to give the title compound as an oil (8.6 mg). | Cc1ccc(NC(=O)c2ccoc2)cc1-c1ccc2c(C)noc2c1 | null | 52.9 | null |
256,477 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[NH:30][N:29]=[N:28][N:27]=4)=[CH:16][CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:31])[CH:3]=1.O.[NH2:33][NH2:34]>>[NH:33]([C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[... | NN | CCc1nc2c(C)cc(Br)nc2n1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-Bromo-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine. (2.0 g), and hydrazine hydrate (15 mL) was heated to 120° C. for 24 hours. Concentration and purification (SiO2, 85/14/2 CH2Cl2 /MeOH/NH4OH) gave 1.80 g of 5-hydrazino-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-... | CCc1nc2c(C)cc(NN)nc2n1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | null | null | null |
501,874 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | C1C=CC=CC=1.[CH2:7]([O:9][C:10](=[O:27])[C:11]([CH3:26])=[CH:12][C:13]1[CH:18]=[C:17]2[CH:19]=[CH:20][C:21]([N+:23]([O-])=O)=[CH:22][C:16]2=[CH:15][CH:14]=1)[CH3:8]>[Fe].O>[CH2:7]([O:9][C:10](=[O:27])[C:11]([CH3:26])=[CH:12][C:13]1[CH:18]=[C:17]2[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:16]2=[CH:15][CH:14]=1)[CH3:8] | CCOC(=O)C(C)=Cc1ccc2cc([N+](=O)[O-])ccc2c1 | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | O | null | null | null | null | null | null | null | null | null | 25 | 1.5 | Into 30 ml of benzene, 2.0 g (7 mmol) of 3-(2-nitro-benzo[d]phenyl)-2-methyl-2-propenoic acid ethyl ester were dissolved; and, with 1.73 g of iron powder (Koso Chem. Co.) and 2.5 ml of distilled water being added thereto under stirring at room temperature, temperature was raised, so that a reaction was carried out for ... | CCOC(=O)C(C)=Cc1ccc2cc(N)ccc2c1 | null | 78.3 | null |
959,389 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | CO/[CH:3]=[C:4]1/[C:5](=[O:20])[NH:6][C:7](=[O:19])[C:8]2[C:13]/1=[CH:12][C:11]([N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)=[CH:10][CH:9]=2.CN(C)C=O.[NH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31]>CCOCC>[O:19]=[C:7]1[C:8]2[C:13](=[CH:12][C:11]([N:14]3[CH:15]=[CH:16][CH:17]=[CH:18]3)=[CH:10][CH:9]=2)/[C:4](=[CH:3]/[N... | NCCCC(=O)O | CO/C=C1/C(=O)NC(=O)c2ccc(-n3cccc3)cc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of (E)-4-(methoxymethylene)-6-(1H-pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione (201 mg, 0.75 mmole), dimethylformamide (5 mL), and 4-aminobutanoic acid (78 mg, 0.75 mmole) is stirred at room temperature for 1 hour. The reaction mixture is diluted with ether, filtered, washed with fresh ether and dried to give a ... | O=C(O)CCCN/C=C1\C(=O)NC(=O)c2ccc(-n3cccc3)cc21 | null | null | null |
1,629,664 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [NH:1]1[C:5]2[CH:6]=[C:7]([C:10]3[O:14][C:13]([SH:15])=[N:12][N:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCO>[CH2:16]([S:15][C:13]1[O:14][C:10]([C:7]2[CH:8]=[CH:9][C:4]3[NH:3][CH:2]=[N:1][C:5]=3[CH:6]=2)=[N:11][N:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18... | Sc1nnc(-c2ccc3nc[nH]c3c2)o1 | BrCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 1 (0.33 g, 1.5 mmol), TEA (0.209 mL, 1.5 mmol), benzyl bromide (0.178 mL, 1.5 mmol) were dissolved in 10 mL of EtOH and kept under reflux overnight. The solvent was removed and the remaining oil was purified by flash-chromatography on silica gel, applying a CHCl3/MeOH gradient. | c1ccc(CSc2nnc(-c3ccc4[nH]cnc4c3)o2)cc1 | null | null | null |
698,870 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | N[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N([O-])=O.[Na+].[BrH:15]>O1CCOCC1.O.[Cu]Br>[Br:15][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5] | N#Cc1cccc(F)c1N | Br | null | [Cu]Br | O=N[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 0 | 2 | To a solution of 2-amino-3-fluorobenzonitrile (17.07 g, 0.125 mol) in 1,4-dioxane (20 ml) was added 48% aqueous hydrobromic acid (200 ml) and the solution was cooled to 0° C. before adding dropwise a solution of sodium nitrite (9.95 g, 0.144 mol) in water (22 ml) over 35 min so that the temperature did not rise above 3... | N#Cc1cccc(F)c1Br | null | 53 | null |
145,232 | ord_dataset-d6cdba90760a47779a36ece5962905eb | null | 1986-01-01T00:06:00 | true | [H-].[Na+].C(OCC)(=O)[CH2:4][C:5]([O:7]CC)=[O:6].Br[CH2:15][C:16]1[O:20][C:19]([CH3:21])=[N:18][C:17]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1>CN(C)C=O.O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:17]2[N:18]=[C:19]([CH3:21])[O:20][C:16]=2[CH2:15][CH2:4][C:5]([OH:7])=[O:6])=[CH:23][CH:24]=1 | CCOC(=O)CC(=O)OCC | Cc1nc(-c2ccc(Cl)cc2)c(CBr)o1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | 0.17 | 60% Sodium hydride in oil (0.6 g) was added portionwise to a solution of diethyl malonate (4.8 g) in N,N-dimethylformamide (50 ml). The mixture was stirred for 10 minutes and a solution of 5-bromomethyl-4-(4-chlorophenyl)-2-methyloxazole (4.30 g) in N,N-dimethylformamide (20 ml) was added dropwise under ice-cooling. Th... | Cc1nc(-c2ccc(Cl)cc2)c(CCC(=O)O)o1 | null | null | null |
713,503 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[CH2:8]([K])[CH3:9].Cl>O>[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4] | CC[K] | O=C(O)CC(=O)O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 0.17 | Ethyl potassium malonate (25.0 g, 0.15 mol) was suspended in water (15.6 ml) and cooled in an ice bath. Concentrated HCl (12.5 ml) was added dropwise over 30 min, then the mixture was stirred for a further 10 min. The precipitate was filtered, then washed twice with ether. The filtrate was separated and the aqueous pha... | CCOC(=O)CC(=O)O | null | 96.9 | null |
554,924 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | [N:1]1([C:8]([NH:10][C@@H:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([OH:14])=O)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([O:23][C:24](=[O:39])[C@@H:25]([NH2:38])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:29][CH:28]=1)([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][... | CC(C)(C)OC(=O)[C@@H](N)Cc1ccc(OC(C)(C)C)cc1 | CC(C)C[C@H](NC(=O)N1CCCCCC1)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of the product from Example Z (2(S)-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid) (0.20 g, 0.78 mmol) and 2(S)-amino-3-(4-tert-butoxy-phenyl)-propionic acid tert-butyl ester (Bachem, 0.284 g, 0.86 mmol) were coupled according to the procedure described in Example 3. The residue was purified by chroma... | CC(C)CC(NC(=O)N1CCCCCC1)C(=O)NC(Cc1ccc(OC(C)(C)C)cc1)C(=O)OC(C)(C)C | null | 23.1 | null |
1,326,497 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][C@H:22]4[NH:27]C(=O)OC(C)(C)C)=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].Cl>O1CCOCC1>[NH2:27][C@H:22]1[C:23]2[C:19](=[C:18]([C:16]3[S:17][C:13]([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH:10... | CC(C)Oc1ccc(-c2ccc(-c3cccc4c3CC[C@H]4NC(=O)OC(C)(C)C)s2)cc1C#N | 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 | 25 | 16 | Prepared using General Procedure 5. To a stirred solution of (R)-tert-butyl 4-(5-(3-cyano-4-isopropoxyphenyl)thiophen-2-yl)-2,3-dihydro-1H-inden-1-ylcarbamate (15 mg, 0.03 mmol) in 1,4-dioxane (1 mL) was added 4N HCl solution in 1,4-dioxane (0.5 mL). The reaction mixture was stirred at room temperature for 16 h. Solven... | CC(C)Oc1ccc(-c2ccc(-c3cccc4c3CC[C@H]4N)s2)cc1C#N | null | 89 | null |
972,031 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [C:1]([O:5][C:6](=[O:45])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:44])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[N:29]4[N:30]=[CH:31][CH:32]=[C:28]4[CH:27]=[C:26]([C:33]4[CH:42]=[CH:41][C:40]5[C:35](=[CH:36][CH:37]=[C:38]([OH:43])[CH:39]=5)[CH:34]=4)[N:25]=3)=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:... | COCCBr | CC(C)(C)OC(=O)NCc1ccc(C(=O)Nc2ccc(Nc3nc(-c4ccc5cc(O)ccc5c4)cc4ccnn34)cc2)cc1 | 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 | 8 | To a solution of (4-{4-[5-(6-hydroxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-benzyl)-carbamic acid tert-butyl ester (compound A3)(120 mg) in DMF (3 ml) are added NaH (8 mg) and 2-bromoethylmethylether (0.019 ml). The mixture is stirred overnight and after extraction the crude product is pu... | COCCOc1ccc2cc(-c3cc4ccnn4c(Nc4ccc(NC(=O)c5ccc(CNC(=O)OC(C)(C)C)cc5)cc4)n3)ccc2c1 | null | 52 | null |
38,094 | ord_dataset-b0ddd49dad024fc7a23ae6f474f9c52f | null | 1978-01-01T00:03:00 | true | [NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][N:7]=1.[C:13]([C:15]([C:21]#[N:22])=[C:16](SC)[S:17][CH3:18])#[N:14]>>[C:13]([C:15]([C:21]#[N:22])=[C:16]([S:17][CH3:18])[NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][N:7]=1)#[N:14] | NCCSCc1ncccc1Cl | CSC(SC)=C(C#N)C#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Reaction of 2-[(2-aminoethyl)thiomethyl]-3-chloropyridine with 1,1-dicyano-2,2-bis-methylthioethylene by the procedure of Example 1(b)(i) yields 1,1-dicyano-2-methylthio-2-[2-((3-chloro-2-pyridyl)methylthio)ethylamino]ethylene. | CSC(NCCSCc1ncccc1Cl)=C(C#N)C#N | null | null | null |
485,878 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [Na].[C:2]1(=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:11]([OH:13])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1.I[CH2:16][CH2:17][CH3:18]>CO>[CH2:16]([S:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][C:2]2=[O:14])=[CH:6][CH:7]=1)(=[O:13])=[O:12])[CH2:17][CH3:18] | CCCI | O=C1CCc2ccc(S(=O)O)cc21 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 0.25 g of sodium is dissolved in 50 ml of anhydrous methanol. 1.96 g of indan-1-one-6-sulfinic acid (see above) are added in portions and the mixture is stirred for 30 min at room temp. 1.87 g of 1-iodopropane are then added and the mixture is stirred for 4 hours at reflux temp. For completion of the reaction, the mixt... | CCCS(=O)(=O)c1ccc2c(c1)C(=O)CC2 | null | null | null |
1,242,231 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [NH2:1][C:2]1[S:3][C:4]([C:10]2[C:15]([F:16])=[CH:14][C:13]([C:17]([OH:20])([CH3:19])[CH3:18])=[CH:12][C:11]=2[F:21])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].Cl[C:23]1[CH:24]=[CH:25][C:26]2[C:27](=[N:29][S:30][N:31]=2)[N:28]=1>>[F:16][C:15]1[CH:14]=[C:13]([C:17]([OH:20])([CH3:18])[CH3:19])[CH:12]=[C:11]([F:21])[C:10]=1[C:4]1... | Clc1ccc2nsnc2n1 | CC(C)(O)c1cc(F)c(-c2cc(C(N)=O)c(N)s2)c(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 title compound was prepared as described in Example 1, Step 5 using 2-amino-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (150 mg, 0.48 mmol) and 5-chloro[1,2,5]thiadiazolo[3,4-b]pyridine (82 mg, 0.48 mmol) as starting materials. LRMS (APCI) calc'd for (C19H16F2N5O2S2) [M+H]+, 448. found... | CC(C)(O)c1cc(F)c(-c2cc(C(N)=O)c(Nc3ccc4nsnc4n3)s2)c(F)c1 | null | null | null |
1,002,747 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [C:1]([NH:5][C:6](=[O:33])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:19]3[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:15]=2)[N:10]=[C:9]1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:34][C:35]([CH3:37])=O.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1>[C:1](... | CC(C)(C)NC(=O)Cn1c(-c2cccc(Cl)c2)nc2ccc(N3CCCNCC3)cc2c1=O | CC(C)=O | null | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | N-tert-Butyl-2-[2-(3-chlorophenyl)-4-oxo-6-perhydro-1,4-diazepin-1-yl-4H-quinazolin-3-yl]acetamide (EXAMPLE 1a) (17 mg, 0.03 mmol), anhydrous acetone (30 μL), sodium cyanoborohydride (3 mg, 0.03 mmol) and glacial acetic acid (12 μL, 0.21 mmol) in anhydrous THF (0.15 mL) was heated in a microwave at 130° C. for 10 minut... | CC(C)N1CCCN(c2ccc3nc(-c4cccc(Cl)c4)n(CC(=O)NC(C)(C)C)c(=O)c3c2)CC1 | null | 47 | null |
287,246 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:12]1[C:17](=[O:18])[N:16]([O:19][C:20](ON2C(=O)CCC2=O)=[O:21])[C:14](=[O:15])[CH2:13]1>C(#N)C>[CH2:12]1[C:17](=[O:18])[N:16]([O:19][C:20]([NH:1][C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][CH:6]=[CH:5][C:4]=3[CH:3]=2)=[O:21])[C:14](=[O:15])[CH... | Nc1ccc2ncccc2c1 | O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O | 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 | 6-Aminoquinolyl-N-hydroxysuccinimidyl carbamate was synthesized according to the following procedure. Acetonitrile (500 ml, Baker analyzed HPLC grade) was distilled to azeotropically remove any water present. The first 50 ml of acetonitrile was discarded. 6-Aminoquinoline (1.5 g, 10 mmol, Aldrich Chemical Co.) was diss... | O=C(Nc1ccc2ncccc2c1)ON1C(=O)CCC1=O | null | null | null |
1,691,451 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [C:1]([NH:4][C:5]1[N:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:6]=1)(=[O:3])[CH3:2].[I:23](O)(=O)=O.II>C(O)C>[C:1]([NH:4][C:5]1[N:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[C:7]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=... | CCOC(=O)Cn1nc(-c2ccc(F)cc2)cc1NC(C)=O | [O-][I+2]([O-])O | null | II | 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 | 60 | 1.5 | To a solution of ethyl 2-(5-acetamido-3-(4-fluorophenyl)-1H-pyrazol-1-yl)acetate (1.1 g, 3.7 mmol) in ethanol (33 mL) were added iodic acid (170 mg, 0.95 mmol) and iodine (480 mg, 1.9 mmol). The reaction was stirred for 90 min at 60° C. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2... | CCOC(=O)Cn1nc(-c2ccc(F)cc2)c(I)c1NC(C)=O | null | 397.9 | null |
1,744,046 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH3:1][C:2]1SC(CNCC)=C(C)[N:6]=1.Cl[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[C:15](OC)[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([NH:6][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1)[CH3:1] | COc1ccc([N+](=O)[O-])c(Cl)n1 | CCNCc1sc(C)nc1C | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 1.0 g of 2,4-dimethyl-5-ethylaminomethylthiazole, 1.5 g of 2-chloro-3-nitro-6-methoxypyridine, 5.0 g of potassium carbonate, 20 mL of N,N-dimethylformamide (DMF) were added into a 150 mL of single-neck flask equipped with a magnetic stirrer. And the reaction mixture was stirred at room temperature overnight. And then e... | CCNc1ncccc1[N+](=O)[O-] | null | null | null |
140,810 | ord_dataset-a2a0fbbcd49a46ffaa432d7ceae8a506 | null | 1986-01-01T00:02:00 | true | [OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)(=[O:27])[CH3:26]>C1(C)C=CC=CC=1>[C:25]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([O:1][C:2]2[CH:17]=[CH:16][... | CC(=O)Oc1ccc(C(=O)Cl)cc1 | O=C(OCc1ccccc1)c1ccc(O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 30 | 0.5 | A 200 ml. four-necked flask equipped with a condenser tube and a thermometer was charged with 36 g of p-acetoxybenzoic acid and 71.4 g of thionyl chloride, and they were reacted at 50° C. for 4 hours. The excess of thionyl chloride was evaporated under reduced pressure to give p-acetoxybenzoyl chloride. Then, a 300 ml ... | CC(=O)Oc1ccc(C(=O)Oc2ccc(C(=O)OCc3ccccc3)cc2)cc1 | null | null | null |
564,804 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | S(OC)(O[CH3:5])(=O)=O.[OH:8][C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11]2[CH:20]=[CH:21][S:22][C:10]=12.[OH-].[K+]>O>[CH3:5][N:12]1[CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9](=[O:8])[C:10]2[S:22][CH:21]=[CH:20][C:11]1=2 | CCOC(=O)c1cnc2ccsc2c1O | COS(=O)(=O)OC | null | [K+] | [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 | 25 | 24 | Dimethyl sulphate (3.9 ml) can be added to a stirred solution of ethyl 7-hydroxythieno[3,2-b]-pyridine-6-carboxylate (4.63 g) and potassium hydroxide (3.5 g) in water (50 ml) at 0-5° C. More water (20 ml) can be added and the mixture can be stirred at ambient temperature for 24 hours. The solid product can be collected... | CCOC(=O)c1cn(C)c2ccsc2c1=O | null | null | null |
987,798 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:20]([S:39]([C:42]3[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=3)(=[O:41])=[O:40])[C:21]([C:23]3[C:27]4=[N:28][C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=[C:26]4[N:25]([CH2:36][CH2:37]I)[CH:24]=3... | C1COCCN1 | COc1cc2c(nc1OC)c(-c1cc3c(Cl)ccnc3n1S(=O)(=O)c1ccc(C)cc1)cn2CCI | 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 | 60 | null | Add morpholine (3.5 equiv., 25.9 mg, 26.1 μmol, 0.30 mmol) and K2CO3 (11.7 mg, 0.085 mmol) to bisazaindole 32 (54 mg, 0.0848 mmol) in CH3CN (6.0 mL). After heating at 60° C. for 30 h, concentrate the reaction medium under vacuum and submit the residue of raw product to flash chromatography on SiO2 (MeOH at 2-4%/CH2Cl2)... | COc1cc2c(nc1OC)c(-c1cc3c(Cl)ccnc3n1S(=O)(=O)c1ccc(C)cc1)cn2CCN1CCOCC1 | null | 257.1 | null |
701,084 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:37]=[CH:36][C:9]([NH:10][C:11]2[N:12]=[C:13]([CH3:35])[C:14]3[CH:20]=[CH:19][C:18](=[O:21])[N:17]([C:22]4[CH:34]=[CH:33][C:25]([C:26]([O:28]C(C)(C)C)=[O:27])=[CH:24][CH:23]=4)[C:15]=3[N:16]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([... | CCOC(=O)c1ccc(Nc2nc(C)c3ccc(=O)n(-c4ccc(C(=O)OC(C)(C)C)cc4)c3n2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | A solution of compound 3 (0.12 g; 0.2397 mmol) and trifluoroacetic acid (0.2 mL; 2.62 mmol) in 3 mL of methylene chloride was stirred at room temperature for 2 h. The reaction mixture was concentrated and the crude product taken up with ethyl acetate and n-hexane to yield compound 9 (0.09 g; 84%). | CCOC(=O)c1ccc(Nc2nc(C)c3ccc(=O)n(-c4ccc(C(=O)O)cc4)c3n2)cc1 | null | 84.5 | null |
332,243 | ord_dataset-1558660634294cc8ad7e01746e9083fd | null | 1996-01-01T00:06:00 | true | [Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([F:21])=[CH:14][C:13]=2[F:22])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:22])=[CH:14][C:15]([F:21])=[C:16]([NH2:18])[CH:17]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:9])([F:8])[F:10] | Cn1nc(-c2cc([N+](=O)[O-])c(F)cc2F)c(Cl)c1C(F)(F)F | null | null | [Fe] | 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 | 80 | 0.5 | A solution of 3.4 g (0.01 mole) 4-chloro-3-(2,4-difluoro-5-nitrophenyl)-1-methyl-5-(trifluoro-methyl)-1H-pyrazole in 50 mL acetic acid was heated to 80° C. under a nitrogen atmosphere. The heat and nitrogen were removed and 1.7 g (0.03 mole) iron powder was added in 3 portions over 5 min. The solution was stirred at 80... | Cn1nc(-c2cc(N)c(F)cc2F)c(Cl)c1C(F)(F)F | null | 78.9 | null |
1,082,403 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8](OCC)=[O:9])=[C:4]([N+:15]([O-])=O)[CH:3]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][CH2:7][C:8](=[O:9])[NH:15][C:4]=2[CH:3]=1 | CCOC(=O)COc1ccc(Cl)cc1[N+](=O)[O-] | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | Iron powder (1.4 g) was added to a solution of the product from step (i) (1.4 g) in acetic acid (30 ml) and the mixture stirred at RT for 1 h. The mixture was filtered and the filtrate evaporated under reduced pressure. Yield 0.44 g | O=C1COc2ccc(Cl)cc2N1 | null | null | null |
152,945 | ord_dataset-5944a40bb4504bbe8185cfdf2a811d03 | null | 1987-01-01T00:01:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]=[CH:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:2]=12.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)(Cl)Cl>[N+:1]1([O-:25])[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]=[CH:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:2]=12 | O=c1c2ccccc2ccc2cccnc12 | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of 1.04 grams (0.005 mole) of benzo[5,6]cyclohepta[1,2-b]pyridin-11-one in 20 milliliters of chloroform was added 1.19 grams (0.0055 mole) of m-chloroperbenzoic acid and the resulting solution stirred at room temperature for 24 hours. At this time an additional 0.6 gram of m-chloroperbenzoic acid was adde... | O=c1c2ccccc2ccc2ccc[n+]([O-])c12 | null | 67.2 | null |
349,129 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | [P:1]([Cl:5])(Cl)([Cl:3])=[O:2].CN1C=CN=C1.[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1>>[P:1]([Cl:5])([Cl:3])(=[O:2])[O:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][CH3:12])=[CH:15][CH:16]=1 | CSc1ccc(O)cc1 | O=P(Cl)(Cl)Cl | null | Cn1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of freshly distilled phosphoryl chloride (45 ml, 0.5 mol) and 1-methylimidazole (0.15 ml), is added 4-(methylthio)phenol (14, 0.1 mol) and the solution is heated under reflux for 20 h. The excess of phosphoryl chloride is removed by distillation and the residue distilled under reduced pressure to give the... | CSc1ccc(OP(=O)(Cl)Cl)cc1 | null | 42.8 | null |
1,422,356 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | Cl[C:2]1[N:13]=[C:12]([NH:14][CH:15]2[CH2:20][CH2:19][CH:18]([N:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]2)[C:11]2[C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C... | Nc1ccccc1 | CN(C)C1CCC(Nc2nc(Cl)nc3sc4c(c23)CCC4)CC1 | null | [Pd] | CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21 | O=C(/C=C/c1ccccc1)/C=C/c1ccccc1 | 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 | 110 | 8 | A solution of 4-N-[10-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]-1-N,1-N-dimethylcyclohexane-1,4-diamine (120 mg, 0.34 mmol, 1.00 equiv) in dioxane (5 mL), was added aniline (60 mg, 0.72 mmol, 2.00 equiv), XantPhos (20 mg, 0.03 mmol, 0.10 equiv) and Pd2(dba)3 (20 mg, 0.02 mmol, 0... | CN(C)C1CCC(Nc2nc(Nc3ccccc3)nc3sc4c(c23)CCC4)CC1 | null | 14.4 | null |
1,417,101 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([O:22]CC)=O)[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH:26]1[CH:30]=[C:29]([CH2:31][CH2:32][NH2:33])[N:28]=[CH:27]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:... | CCOC(=O)c1c(O)c2ncc(Cc3ccc(F)cc3)cc2[nH]c1=O | NCCc1c[nH]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 | This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-(1H-imidazol-4-yl)ethylamine employing methods similar to those described in Example 11 and was obtained as an off-white solid: 1H NMR (CF3CO2D) δ 8.66 (1H, s), 8.60 (1H, s), 8.43 (1H, s), ... | O=C(NCCc1c[nH]cn1)c1c(O)c2ncc(Cc3ccc(F)cc3)cc2[nH]c1=O | null | null | null |
1,406,905 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:13])[NH:6]2.[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[O:22][C:23]([CH2:26]Cl)=[N:24][N:25]=2)[CH:20]=1>>[Br:14][C:15]1[CH:20]=[C:19]([C:21]2[O:22][C:23]([CH2:26][N:6]3[C:7]4[C:3](=[C:2]([Cl:1])[C:10]([C:11]#[N:12])=[CH:9][CH:8]=4)[CH... | ClCc1nnc(-c2cncc(Br)c2)o1 | Cc1cc2c(Cl)c(C#N)ccc2[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesized as described in Example 4 from 4-chloro-2-methyl-1H-indole-5-carbonitrile and 3-bromo-5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridine: 1H NMR (400 MHz, DMSO-d6) δ 9.05 (s, 1H), 8.94 (s, 1H), 8.48 (s, 1H), 7.96 (s, 1H), 7.85 (d, J=8.5 Hz, 1H), 7.63 (d, J=8.5 Hz, 1H), 5.96 (s, 2H), 2.47 (s, 3H); MS (ES) m/z... | Cc1cc2c(Cl)c(C#N)ccc2n1Cc1nnc(-c2cncc(Br)c2)o1 | null | null | null |
1,430,144 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:15]([CH2:22][CH3:23])[C:16](N(OC)C)=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:24]([N:14]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C@@H:15]([CH2:22][CH3:23])[CH:16]=[O:17])[C:25... | CC[C@@H](C(=O)N(C)OC)N(Cc1ccccc1)Cc1ccccc1 | 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 | -30 | 2.5 | Under an atmosphere of argon, at −20 to −30° C., LiAlH4 (2.34 g, 61.8 mmol, Eq: 1.2) was combined with THF (150 ml) to give a light grey suspension. Then (S)-2-(dibenzylamino)-N-methoxy-N-methylbutanamide (24 g, 51.5 mmol, Eq: 1.00), diluted in THF (50 ml) was added at −30° C. The reaction was stirred for 2.5 h at −30°... | CC[C@@H](C=O)N(Cc1ccccc1)Cc1ccccc1 | null | null | null |
1,702,237 | 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=[CH:7][C:6]=2[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=1.[Cl:18][C:19]1[CH:24]=[C:23](B(O)O)[CH:22]=[CH:21][N:20]=1>>[Cl:18][C:19]1[CH:24]=[C:23]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[CH:7][C:6]=3[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=2)[CH... | N#Cc1cc(Br)c2c(c1)cc1n2CCNC1=O | OB(O)c1ccnc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, off-white solid (68 mg, 84%), MS (ISN) m/z=323.5 [(M+H)+], mp 286° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 15) (72.5 mg, 0.25 mmol) and commercially available 2-chloro-pyridin-4-ylbor... | N#Cc1cc(-c2ccnc(Cl)c2)c2c(c1)cc1n2CCNC1=O | null | null | null |
1,384,478 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH:12]([C:16]1[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)[C:13]([OH:15])=[O:14])=[O:4].[N:24]12[CH2:31][CH2:30][CH:27]([CH2:28][CH2:29]1)[C@@H:26](O)[CH2:25]2.O.N1(O)C2C=CC=CC=2N=N1.C(=NC1CCCCC1)=NC1CCCCC1>C1COCC1>[CH3:23][O:22][C:19]1[N:18]=[... | COC(=O)c1ccccc1NC(C(=O)O)c1ccc(OC)nc1 | O[C@H]1CN2CCC1CC2 | null | C(=NC1CCCCC1)=NC1CCCCC1 | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 2-(2-(methoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (I79) (118 mg, 0.37 mmol), (R)-quinuclidin-3-ol (52.2 mg, 0.41 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (62.8 mg, 0.41 mmol), and N,N′-methanediylidenedicyclohexanamine (85 mg, 0.41 mmol) was dissolved in dry THF (10 ml) and stirr... | COC(=O)c1ccccc1NC(C(=O)O[C@H]1CN2CCC1CC2)c1ccc(OC)nc1 | null | null | null |
179,385 | ord_dataset-4d84abdf99524e0fb6c42ab2a3300790 | null | 1988-01-01T00:10:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][N:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[C:6](=[O:20])[C:5]2=O.Cl.[NH2:23][NH:24][C:25]([NH2:27])=[O:26]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][N:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:... | CC(C)N(CCN1C(=O)C(=O)c2cc(Br)ccc21)C(C)C | NNC(N)=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By using 5-bromo-1-(2-diisopropylaminoethyl)isatin and semicarbazide hydrochloride, a method analogous to that described in Example 4 was carried out to obtain (E)-5-bromo-1-(2-diisopropylaminoethyl)isatin 3-semicarbazone having a melting point of 149°-153° C. (yield: 72.6%, recrystallizing solvent: chloroform-hexane). | CC(C)N(CCN1C(=O)/C(=N/NC(N)=O)c2cc(Br)ccc21)C(C)C | null | 72.6 | null |
460,302 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([CH:17](C(O)=O)[C:18]([OH:20])=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:17][C:18]([OH:20])=[O:19] | CCCCCC(c1ccc(OC)cc1OC)C(C(=O)O)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 6.57 g of 2-[1-(2,4-dimethoxyphenyl)hexyl]malonic acid [prepared as described in step (i) above] in 60 ml of xylene was heated under reflux for 3 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography ... | CCCCCC(CC(=O)O)c1ccc(OC)cc1OC | null | 74 | null |
1,289,225 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[C:11]([O:13]CC)=O.O=S(Cl)[Cl:18]>C1(C)C=CC=CC=1.[OH-].[Na+]>[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[C:11]([Cl:18])=[O:13] | CCOC(=O)c1c(C(F)F)nn(C)c1F | O=S(Cl)Cl | null | [Na+] | [OH-] | 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 | 80 | null | A solution of 22.3 g (100 mmol) of ethyl 5-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate in 100 ml of toluene and 50 ml of 10% NaOH are stirred at AT for 3 hours. The aqueous phase is separated and adjusted to pH 5 with HCl. After extracting the product with chlorobenzene and azeotropically drying the orga... | Cn1nc(C(F)F)c(C(=O)Cl)c1F | null | null | null |
817,087 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | CS([C:5]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[S:7][N:6]=1)(=O)=O.[CH2:17]([OH:21])[C:18]#[C:19][CH3:20].[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[Cl:16][C:12]1[CH:11]=[C:10]([C:8]2[S:7][N:6]=[C:5]([O:21][CH2:17][C:18]#[C:19][CH3:20])[N:9]=2)[CH:15]=[CH:14][CH:13]=1 | CC#CCO | CS(=O)(=O)c1nsc(-c2cccc(Cl)c2)n1 | null | [Cl-] | [H-] | [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 | null | 0.5 | In 2.5 ml of N,N-dimethylformamide, 350 mg of 3-methylsulfonyl-5-(3-chlorophenyl)-1,2,4-thiadiazole and 98 mg of 2-butyne-1-ol were dissolved, to the resulting solution was added 56 mg of sodium hydride (60% oily) with ice-cooling, and the mixture was stirred for 30 minutes, and further stirred at room temperature for ... | CC#CCOc1nsc(-c2cccc(Cl)c2)n1 | null | 86 | null |
1,252,873 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH:23]=O)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[CH3:26][O:27][CH2:28][CH2:29][NH2:30]>>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:... | COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2C=O)c1 | COCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the procedure described in Example 1, Step 5, using the following starting materials: (2′-formyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester and 2-methoxyethylamine. | COCCNCc1cc(C(F)(F)F)ccc1-c1cc(CC(=O)OC)ccc1OC | null | null | null |
1,403,145 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[O:22][C:16]3=[CH:17][N:18]=[C:19](Cl)[CH:20]=[C:15]3[CH2:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)(=[O:26])=[O:25]>>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[O:22][C:16]3=[CH:1... | CC(C)OC(=O)N1CCC(C2Cc3cc(Cl)ncc3O2)CC1 | CS(=O)(=O)c1ccc(B(O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid isopropyl ester and 4-(methanesulfonyl)phenylboronic acid following a procedure analogous to that described in Example 28. LC (method 7): tR=1.26 min; Mass spectrum (ESI+): m/z=445 [M+H]+. | CC(C)OC(=O)N1CCC(C2Cc3cc(-c4ccc(S(C)(=O)=O)cc4)ncc3O2)CC1 | null | null | null |
582,728 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]2[CH2:15][C@H:14]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]([NH:25][C:26]4[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:33])=[O:24])[CH2:18][CH2:17]3)[CH2:13][CH2:12][N:11]2C(OCC)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[K+]>CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]2[CH... | CCOC(=O)N1CC[C@@H](N2CCN(CC(=O)Nc3c(C)cccc3C)CC2)C[C@@H]1Cc1ccc(Cl)c(Cl)c1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of intermediate 11 (0.0034 mol) and potassium hydroxide (0.034 mol) in 2-propanol (150 ml) was stirred and refluxed for 4 days. The solvent was evaporated. The residue was taken up in CH2Cl2/water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by col... | Cc1cccc(C)c1NC(=O)CN1CCN([C@@H]2CCN[C@@H](Cc3ccc(Cl)c(Cl)c3)C2)CC1 | null | 30 | null |
1,627,220 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[CH:4][CH:3]=1.[C:16]1(=O)[CH:21]=[CH:20][C:19](=[O:22])[CH:18]=[CH:17]1>C(O)C.CC(OC)(C)C.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[O:7][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=3[C:8]=2[C:9]([O:11][CH2:1... | O=C1C=CC(=O)C=C1 | CCOC(=O)CC(=O)c1ccc(Cl)cc1 | null | [Cl-] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | COC(C)(C)C | null | null | null | null | null | null | null | null | null | 95 | 0.5 | Zinc chloride (28.3 g, 0.207 mol) was stirred in anhydrous ethanol (45 mL) then heated to 95° C. (reflux) under nitrogen atmosphere using oven dried glassware. Ethyl 4-chlorobenzoylacetate (44 g, 0.194 mol) was added as a single portion followed by dropwise addition of a solution of benzoquinone (22.6 g, 0.21 mol) in a... | CCOC(=O)c1c(-c2ccc(Cl)cc2)oc2ccc(O)cc12 | null | 43.9 | null |
620,590 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[CH2:4][NH:5][C:6]([C@@H:8]1[C:12]([CH3:14])([CH3:13])[S:11][CH2:10][N:9]1[C:15](=[O:29])[C@@H:16]([OH:28])[C@@H:17]([NH2:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:7].C([O:37][C:38]1[C:39]([CH3:48])=[C:40]([CH:44]=[CH:45][C:46]=1[F:47... | CC(=O)Oc1c(F)ccc(C(=O)O)c1C | COc1ccc(C[C@H](N)[C@H](O)C(=O)N2CSC(C)(C)[C@H]2C(=O)NCc2ccccc2C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The reaction was carried out in the same manner as in Step 3 of Example 1 using the compound obtained in Step 2 of Example 1 (94 mg) and 3-acetoxy-4-fluoro-2-methylbenzoic acid (45 mg). The resulting crude product was purified by recryatallization from a mixture of EtOAc and n-hexane to obtain the target compound (84 m... | COc1ccc(C[C@H](NC(=O)c2ccc(F)c(O)c2C)[C@H](O)C(=O)N2CSC(C)(C)[C@H]2C(=O)NCc2ccccc2C)cc1 | null | 67.6 | null |
1,413,319 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [I:1][C:2]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([C:19]([F:22])([F:21])[F:20])[C:3]=1[NH2:4].[N+:23]([C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30])([O-:25])=[O:24]>>[I:1][C:2]1[CH:8]=[C:7]([C:9]([F:18])([C:10]([F:11])([F:12])[F:13])[C:14]([F... | O=C(Cl)c1cccc([N+](=O)[O-])c1 | Nc1c(I)cc(C(F)(C(F)(F)F)C(F)(F)F)cc1C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | According to the method of 4-3 of Example 4, a target compound was prepared from 2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline and 3-nitrobenzoyl chloride. | O=C(Nc1c(I)cc(C(F)(C(F)(F)F)C(F)(F)F)cc1C(F)(F)F)c1cccc([N+](=O)[O-])c1 | null | null | null |
560,849 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH2:16][C:17]#[N:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni]>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | N#CCCOC1CCN(Cc2ccccc2)CC1 | [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 | 10 g (40.9 mmol) 3-(1-benzylpiperidin-4-yloxy)-propionitrile are dissolved in 100 ml ethanol and added to a spatula tip Raney-Nickel. The mixture is stirred at RT and under hydrogen atmosphere until the consumption of the theoretical amount of hydrogen to be taken up (ca. two days). Subsequently, this is filtered from ... | NCCCOC1CCN(Cc2ccccc2)CC1 | null | null | null |
977,775 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | Cl.[NH2:2][CH:3]([C:10]([C:12]1[S:13][C:14]([Cl:17])=[CH:15][CH:16]=1)=[O:11])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[Cl:17][C:14]1[S:13][C:12]([C:10](=[O:11])[CH:3]([NH:2][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]... | O=C(Cl)c1ccc(F)cc1 | CCOC(=O)CC(N)C(=O)c1ccc(Cl)s1 | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | O | null | null | null | null | null | null | null | null | null | 25 | 2 | A mixture of ethyl 3-amino-4-(5-chlorothiophen-2-yl)-4-oxobutyrate hydrochloride (596 mg), 4-fluorobenzoyl chloride (380 mg) and sodium hydrogen carbonate (1.0 g) in ethyl acetate (10 ml) and water (10 ml) was stirred at room temperature for 2 hours. To the reaction mixture were added ethyl acetate (30 ml) and water (3... | CCOC(=O)CC(NC(=O)c1ccc(F)cc1)C(=O)c1ccc(Cl)s1 | null | 95.4 | null |
418,269 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:23][CH:22]=2)=[O:20])=[CH:15][CH:14]=1.[CH3:39][Mg]Br>C1COCC1>[N:1]1[C:10]2[... | C[Mg]Br | O=C(c1ccc(OCc2ccc3ccccc3n2)cc1)c1ccc(OCc2ccc3ccccc3n2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 12 | To a -78° C. solution in THF (20 mL) of bis(4-(2-quinolylmethoxy)phenyl) ketone (992 mg, 2 mmol), prepared as in step 1, was added methylmagnesium bromide (3M solution in ethyl ether, 0.8 mL, 2.4 mmol) and the resulting mixture was stirred at room temperature for 12 hours. The mixture was then quenched with saturated a... | CC(O)(c1ccc(OCc2ccc3ccccc3n2)cc1)c1ccc(OCc2ccc3ccccc3n2)cc1 | null | 89.7 | null |
235,405 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | [Si]([O:8][CH:9]([CH2:22][O:23][CH2:24][P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[CH2:10][O:11][N:12]1[CH:20]=[N:19][C:18]2[C:13]1=[N:14][CH:15]=[N:16][C:17]=2[NH2:21])(C(C)(C)C)(C)C>C(O)(=O)C>[CH2:28]([O:27][P:25]([CH2:24][O:23][CH2:22][CH:9]([OH:8])[CH2:10][O:11][N:12]1[CH:20]=[N:19][C:18]2[C:13]1... | CCOP(=O)(COCC(COn1cnc2c(N)ncnc21)O[Si](C)(C)C(C)(C)C)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 9-[2-(t-butyldimethylsilyloxy)-3-(diethoxyphosphorylmethoxy)propoxy]adenine (410 mg, 0.84 mmol) in 80% acetic acid (20 ml) was stirred at 85° C. for 4 h. The solvents were evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 10:1, affording 9-[3-(diethoxyphosphor... | CCOP(=O)(COCC(O)COn1cnc2c(N)ncnc21)OCC | null | 74.5 | null |
1,504,167 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [NH2:1][C@H:2]1[C:7]([F:9])([F:8])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:10][C:11]1[N:12]=[C:13]([NH:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][CH:24]=[CH:23]3)[C:14]([C:17]#[N:18])=[N:15][CH:16]=1.[OH-].[Na+].OO.CC(O)=[O:36]>CCO.CS(C)=O>[NH2:1][C@H:2]1[C:7]([F:8])([F:9])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH... | CC(=O)O | N#Cc1ncc(N[C@@H]2CCCC(F)(F)[C@@H]2N)nc1Nc1ccc2ncccc2c1 | null | OO | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CCO | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A mixture of 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-chloropyrazine-2-carbonitrile (97 mg, 0.241 mmol), 6-aminoquinoline (50 mg, 0.347 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (10 mg, 0.044 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. Water... | NC(=O)c1ncc(N[C@@H]2CCCC(F)(F)[C@@H]2N)nc1Nc1ccc2ncccc2c1 | null | null | null |
618,041 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][C@H:11]([S:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][C@H:9]2[CH2:33][O:34][CH2:35][C:36]2[CH:41]=[C:40]([F:42])[C:39]([F:43])=[CH:38][C:37]=2[F:44])[CH:5]=[CH:4][N:3]... | Fc1cc(F)c(COC[C@@H]2C[C@@H](SC(c3ccccc3)(c3ccccc3)c3ccccc3)CN2c2ccnc(Cl)n2)cc1F | C[O-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 75 | null | A solution of 0.24 (0.4 mmol) (2S,4R)-2-Chloro-4-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine in 1 ml MeOH was treated at 0° C. with 0.16 ml (0.88 mmol) sodium methylate (5.5 M in MeOH) and kept at this temperature (2 h), warmed up and heated for 10 h at 75° C. After evaporation and... | COc1nccc(N2C[C@H](SC(c3ccccc3)(c3ccccc3)c3ccccc3)C[C@H]2COCc2cc(F)c(F)cc2F)n1 | null | 77 | null |
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