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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,561,452 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:21][CH2:22][C:23]([C@@H:26]4[CH2:30][O:29]C(C)(C)[O:27]4)([CH3:25])[CH3:24])[CH:14]=[C:15]([F:20])[CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[ClH:33]>CO>[ClH:33].[ClH:33].[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:21... | CC1(C)OC[C@@H](C(C)(C)COc2cc(F)cc3ccc(-c4nnc5ccccn45)nc23)O1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 0.5 | (R)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropoxy)-6-fluoroquinoline (0.190 g, 0.435 mmol) was added to methanol saturated with HCl and stirred for 30 minutes. The solution was evaporated, DCM was added, and the material triturated and filtered to yield 140 mgs of the desi... | CC(C)(COc1cc(F)cc2ccc(-c3nnc4ccccn34)nc12)[C@@H](O)CO | null | null | null |
1,697,336 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[N:34]1[CH:39]=[CH:38][C:37]([C:40]2[C:44]3[C:45](=[O:49])[NH:46][CH:47]=[CH:48][C:43]=3[O:42][CH:41]=2)=[CH:36][CH:35]=1.[N:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:53]=[CH:52][C:51]=1[CH2:60][CH2:61]O.Cl>C1COCC1.CC(=O)OCC>[N:34]1[CH:35]=... | O=c1[nH]ccc2occ(-c3ccncc3)c12 | OCCc1ccc2ccccc2n1 | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | Cl | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 15 | 8 | To a solution of triphenylphosphine (247 mg, 0.942 mmol) in THF (10 mL), DIAD (0.321 mL, 1.65 mmol) was added. The mixture was cooled to 15° C. 3-(Pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one (100 mg, 0.471 mmol) and 2-(quinolin-2-yl)ethanol from example from example a1 were added. After stirring overnight at room tempera... | O=c1c2c(-c3ccncc3)coc2ccn1CCc1ccc2ccccc2n1 | null | 36.3 | null |
279,595 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | [F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[N:15]1[C:19]([NH:20][C:21]([CH2:23][O:24]C(C)=O)=[O:22])=[C:18]([N+:28]([O-:30])=[O:29])[CH:17]=[N:16]1.[OH-].[Na+].Cl>C(O)C.O>[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[N:15]1[... | CC(=O)OCC(=O)Nc1c([N+](=O)[O-])cnn1-c1c(F)c(F)c(C(F)(F)F)c(F)c1F | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 25 | 0.25 | A mixture of 1.5 grams (0.0034 mole) of 1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)-5-methylcarbonyloxymethylcarbonylamino-4-nitropyrazole, 2.63 mL of a 2N aqueous sodium hydroxide solution, 1.5 mL of ethanol, and 4.7 mL of water was stirred at room temperature for 15 minutes. After the pH was adjusted to 5.0 with ... | O=C(CO)Nc1c([N+](=O)[O-])cnn1-c1c(F)c(F)c(C(F)(F)F)c(F)c1F | null | 54.8 | null |
810,370 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [CH3:1][O:2][C:3]([CH:5]1[C:11](=O)[CH2:10][CH:9]([C:13]([O:15][CH3:16])=[O:14])[C:7](=O)[CH2:6]1)=[O:4].[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.Cl>CO>[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:7]2[CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:11]([NH:23][C:22]3[CH:24]=[CH:25][C:19](... | COC(=O)C1CC(=O)C(C(=O)OC)CC1=O | COc1ccc(N)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate (9.12 gm; 40 mmol) and methanol (200 ml) were heated to boiling, then 4-methoxyaniline (10.84 gm; 88 mmol) was added followed by conc. hydrochloric acid (400 μl). The mixture was refluxed for 2.5 hours under a nitrogen atmosphere. On cooling, an orange solid precipitated ... | COC(=O)C1=C(Nc2ccc(OC)cc2)CC(C(=O)OC)=C(Nc2ccc(OC)cc2)C1 | null | 96.9 | null |
1,411,756 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:15](=[O:25])[CH2:14]1)C(=O)OCC1C=CC=CC=1>CO>[CH3:1][NH:2][CH:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:15](=[O:25])[CH2:14]1 | CN(C(=O)OCc1ccccc1)C1CCN(c2ccncc2)C(=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 | 4 | Benzyl methyl(2-oxo-1-(pyridin-4-yl)piperidin-4-yl)carbamate (300 mg, 0.885 mmol, 1.0 eq.) was dissolved in MeOH and degassed with N2. Pd(OH)2 (240 mg) was then added and hydrogenation was carried out for 4 hours. After monitoring by TLC, the reaction mixture was filtered over Celite, the filtrate was concentrated unde... | CNC1CCN(c2ccncc2)C(=O)C1 | null | 77 | null |
820,041 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[O:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].[O:21]=[CH:22][C:23]1[CH:31]=[CH:30][C:28]([OH:29])=[C:25]([O:26][CH3:27])[CH:24]=1.CN(C)C=O>O>[CH3:27][O:26][C:25]1[CH:24]=[C:23]([CH:31]=[CH:30][C:28]=1[O:29][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:10]=[N:... | Cc1oc(-c2cccnc2)nc1CCl | COc1cc(C=O)ccc1O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 90 | 2 | A mixture of 3-(4-chloromethyl-5-methyl-1,3-oxazol-2-yl)pyridine (3.00 g), potassium carbonate (1.89 g), vanillin (2.08 g) and N,N-dimethylformamide (50 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed w... | COc1cc(C=O)ccc1OCc1nc(-c2cccnc2)oc1C | null | 81.4 | null |
1,094,845 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:33])=[C:6]([S:8]([N:11]2[C:16]3[CH:17]=[C:18]([C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=4)=[O:22])[CH:19]=[CH:20][C:15]=3[O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.F[C:35]1C=CC(C)=C(S(Cl)(=O)=O)[CH:40]=1>>[CH2:35]([O:29][C:28](=[O:30])[C:2... | Cc1ccc(F)cc1S(=O)(=O)Cl | Cc1ccc(F)cc1S(=O)(=O)N1CCOc2ccc(C(=O)Nc3ccc(C(=O)O)cc3)cc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-{[4-(5-Fluoro-2-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=468.9 (M−H), was prepared as described for example 14, steps 1 to 8. Step 7 was performed using 5-fluoro-2-methyl-benzenesulfonyl chloride and yielded 4-{[4-(5-fluoro-2-methyl-benzenesulfonyl)-3,4-d... | CCOC(=O)c1ccc(NC(=O)c2ccc3c(c2)N(S(=O)(=O)c2cc(F)ccc2C)CCO3)cc1 | null | null | null |
368,765 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | Br[CH2:2][CH2:3]Br.[S:5]([O-:8])([O-:7])=[O:6].[Na+:9].[Na+]>O>[CH2:2]([S:5]([O-:8])(=[O:7])=[O:6])[CH2:3][S:5]([O-:8])(=[O:7])=[O:6].[Na+:9].[Na+:9] | O=S([O-])[O-] | BrCCBr | null | [Na+] | 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 1,2-dibromoethane (37.6 g, 0.20 tool) and sodium sulfite (63.0 g, 0.5 mol) in water (225 mL) was heated at reflux temperature for 20 h. After the mixture was cooled in the refrigerator, crystals were collected. The crude product was repeatedly recrystallized from water-ethanol. The trace amount of inorgani... | O=S(=O)([O-])CCS(=O)(=O)[O-] | null | 65.1 | null |
1,071,775 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [CH:1]([Mg]Cl)([CH3:3])[CH3:2].[C:6]([O:10][C:11](=[O:21])[NH:12][CH:13]1[CH2:18][CH2:17][CH:16]([CH:19]=[O:20])[CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7]>C1COCC1>[C:6]([O:10][C:11](=[O:21])[NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([CH:19]([C:11]2[O:10][C:1]3[CH:3]=[CH:8][CH:6]=[CH:7][C:2]=3[N:12]=2)[OH:20])[CH2:17][CH... | CC(C)[Mg]Cl | CC(C)(C)OC(=O)NC1CCC(C=O)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 | 0 | 1 | To a solution of 4-methoxy-benzoxazole (1490 mg, 10 mmol, obtained by methylation of 4-hydroxybenzoxazole (J. Med. Chem. (1987), 30, 62) in THF (60 ml) was added dropwise a solution of i-PrMgCl (5 ml, 2M solution in THF). The red mixture was stirred at 0° C. for 1 h before dropwise addition of (4-formyl-cyclohexyl)-car... | CC(C)(C)OC(=O)N[C@H]1CC[C@H](C(O)c2nc3ccccc3o2)CC1 | null | null | null |
639,851 | ord_dataset-1c0bae7388cf460091d56129e95b3145 | null | 2004-01-01T00:06:00 | true | [O-:1][N+:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][OH:12].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>>[CH2:17]([O:16][C:14]([N:8]([CH2:9][CH2:10][CH2:11][OH:12])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N+:2]=1[O-:1])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]... | O=C(Cl)OCc1ccccc1 | [O-][n+]1ccccc1NCCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-[N-benzyloxycarbonyl-N-(1-oxido-2-pyridinyl)amino] propanol was prepared by reaction of 3-[N-(1-oxido-2-pyridinyl)amino] propanol (obtained as described in MILLER, W. H. et al. Bioorg. Med. Chem. Lett. 1999, 9 1807-1812) with benzyl chloroformate according to the standard procedure. | O=C(OCc1ccccc1)N(CCCO)c1cccc[n+]1[O-] | null | null | null |
1,440,151 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([C:11]2[N:30]=[C:14]3[CH:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])[CH2:16][CH2:17][CH2:18][CH2:19][N:13]3[N:12]=2)[CH:8]=[CH:7][C:6]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1.CN(C=[O:41])C>>[CH3:3][O:4][C:5]1[N:10]=[C:9]([C:11]2[N:30]=... | COc1nc(-c2nc3n(n2)CCCCC3c2ccccc2C(F)(F)F)ccc1-n1cnc(C)c1 | CN(C)C=O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 96 | Sodium hydride (60%) was added to a solution of 2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-9-(2-trifluoromethylphenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepine obtained in Examples 74 and 75 (83 mg) in DMF (5 mL) with stirring under ice-cooling until bubbling was stopped. Thereafter, the mixture... | COc1nc(-c2nc3n(n2)CCCCC3(O)c2ccccc2C(F)(F)F)ccc1-n1cnc(C)c1 | null | null | null |
1,396,182 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][NH:12]3)[N:5]=[C:4]2[N:17]([CH3:20])[N:18]=[CH:19][C:3]=12.[CH3:21][S:22][CH2:23][CH2:24][CH2:25][NH2:26]>>[NH:12]1[C:13]2[C:9](=[C:8]([C:6]3[N:5]=[C:4]4[N:17]([CH3:20])[N:18]=[CH:19][C:3]4=[C:2]([NH:26][CH2:25][CH2:24][CH2:23][S:22][CH3:21]... | Cn1ncc2c(Cl)cc(-c3cccc4[nH]ncc34)nc21 | CSCCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine 7 (100 mg) and 3-(methylthio)propylamine (3 equiv.) were heated in microwave at 170° C. for one hour following General Procedure B. Volatiles were removed in vacuo; the residue was purified by prep HPLC to give [6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,... | CSCCCNc1cc(-c2cccc3[nH]ncc23)nc2c1cnn2C | null | null | null |
2,742 | ord_dataset-a0bc986c3cf848c2a1ea93b297d1ad89 | null | 1976-01-01T00:02:00 | true | [C:1]([NH:5][CH2:6][CH:7]([OH:26])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[N:18][S:19][C:20]=2[C:21]([O:23]CC)=[O:22])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+]>O>[C:1]([NH:5][CH2:6][CH:7]([OH:26])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[N:18][S:19][C:20]=2[C:21]([OH:23])=[... | CCOC(=O)c1snnc1-c1ccc(OCC(O)CNC(C)(C)C)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | To a solution of 200 mg. of 4-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-5-carboethoxy-1,2,3-thiadiazole in 15 ml. of methanol is added a solution of 100 mg. of sodium hydroxide in 2 ml. of water, and the reaction mixture is refluxed for 4 hours. It is then cooled, evaporated to a small volume under vacuo, diluted with... | CC(C)(C)NCC(O)COc1ccc(-c2nnsc2C(=O)O)cc1 | null | null | null |
892,247 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)[CH:9]=2)[CH2:4][CH2:3][NH:2]1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:21]([N:2]1[CH2:3][CH2:4][C:5]2[C:10]... | NC(=O)c1ccc(Oc2ccc3c(c2)CNCC3)nc1 | O=Cc1ccccc1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | Combine 6-(1,2,3,4-tetrahydro-isoquinolin-7-yloxy)-nicotinamide (94 mg, 0.35 mmol), benzaldehyde (37 μL, 0.37 mmol), sodium triacetoxyborohydride (96 mg 0.46 mmol), acetic acid (21 μL, 0.37 mmol), and 1,2-dichloroethane (5 mL) then stir at room temperature for 18 hours. Dilute the reaction with saturated aqueous sodium... | NC(=O)c1ccc(Oc2ccc3c(c2)CN(Cc2ccccc2)CC3)nc1 | null | 25.7 | null |
1,244,957 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23](=[S:33])[NH:24][C:25]5[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=5[CH3:32])[CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:34]I>ClCCl>[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([C... | Cc1ccc(C)c(NC(=S)N2CCC(c3nc(C4=NOC(c5ccccc5)C4)cs3)CC2)c1 | CI | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 14-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarbothioamide (i.e. the product of Step C) (476 mg, 1.0 mmol) and methyl iodide (0.25 mL, 4.0 mmol) in dichloromethane (2 mL) was agitated at room temperature for 3 h. The reaction mixture was then diluted with dich... | CSC(=Nc1cc(C)ccc1C)N1CCC(c2nc(C3=NOC(c4ccccc4)C3)cs2)CC1 | null | null | null |
424,928 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[C:20]([CH2:21][OH:22])=[CH:19][CH:18]=[CH... | COC(=O)c1cccnc1N(C)C1CCN(Cc2ccccc2)CC1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1.5 | To a flame-dried flask containing 1-benzyl-4-(N-methyl-N-(3-methoxycarbonyl-2-pyridyl)amino)piperidine (XXIX, EXAMPLE 34, 750 mg) in dry tetrahydrofuran (22 ml) at 0° under nitrogen is added lithium aluminum hydride (84 mg) in two portions. The mixture is stirred at 0° for 1.5 hrs, quenched carefully with aqueous sodiu... | CN(c1ncccc1CO)C1CCN(Cc2ccccc2)CC1 | null | null | null |
757,596 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:10][N:11]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)[CH:12]=1)=[O:5])[CH3:2].[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1.O.ON1C2C=CC=CC=2N=N1.CCN=... | NCc1ccc(C(F)(F)F)cc1 | CCOC(=O)CCc1cn(Cc2ccc(C(=O)O)cc2)nc1-c1ccccc1 | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 13 | A mixture of 4-[4-(2-ethoxycarbonylethyl)-3-phenyl-1H-pyrazol-1-ylmethyl]benzoic acid (500 mg), 4-trifluoromethylbenzylamine (250 mg), 1-hydroxybenzotriazole monohydrate (210 mg), WSC (270 mg), and N,N-dimethylformamide (10 ml) was stirred at room temperature for 13 hours. The reaction mixture was poured into water, wh... | CCOC(=O)CCc1cn(Cc2ccc(C(=O)NCc3ccc(C(F)(F)F)cc3)cc2)nc1-c1ccccc1 | null | 77.7 | null |
820,081 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [NH2:1][C:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[NH2:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:3]=1 | Nc1nn(-c2ccccc2)cc1CO | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | A mixture of (3-amino-1-phenyl-1H-pyrazol-4-yl)methanol (12.29 g), activated manganese dioxide (35 g) and tetrahydrofuran (200 mL) was stirred at room temperature for 16 hrs. The reaction mixture was filtered, and the filtrate was concentrated. Recrystallization of the residue from tetrahydrofuran-hexane gave 3-amino-1... | Nc1nn(-c2ccccc2)cc1C=O | null | 82.4 | null |
262,864 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | [CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:54])=[CH:44][CH:45]2[C... | CCC1C=C(C)C(F)C(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(=O)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | NCc1ccccc1 | null | [BH3-]C#N | [Na+] | 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 | 25 | 0.5 | To a solution of 17-ethyl-20-fluoro-1, 14-dihydroxy-12-[2'-(3"-methoxy-4"-oxocyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ] octacos-18-ene-2,3,10,16-tetraone from Example 24 (79.7 mg) in dry isopropyl alcohol (3 ml) is added benzylamine (86.5 mg). The mixture... | CCC1C=C(C)C(F)C(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(NCc4ccccc4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | null | null | null |
635,700 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[CH3:9][CH:10]([CH3:26])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:15]=1)=[O:12]>>[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:23]1[CH2:24][CH2:25][CH:20]([C:16]2[CH:15]=[C:14]([NH:13][C:11](=[O:12])[CH... | CC(C)C(=O)Nc1cccc(C2CCNCC2)c1 | OCCCCCCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by Procedure G and Scheme B1 using 6-chloro-1-hexanol and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: ESMS m/e: 347.3 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(CCCCCCO)CC2)c1 | null | null | null |
596,468 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | [CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[N:13]1[C:20]([Cl:21])=[N:19][C:17](Cl)=[N:16][C:14]=1[Cl:15]>O1CCCC1>[Cl:15][C:14]1[N:13]=[C:20]([Cl:21])[N:19]=[C:17]([N:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=[C:2]2[CH3:1])[N:16]=1 | Cc1nc2ccccc2[nH]1 | Clc1nc(Cl)nc(Cl)n1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 1 | 2-Methylbenzimidazole (5.0 g) was dissolved in tetrahydrofuran (50 ml), and sodium hydride (60% purity, oily) (1.6 g) was added thereto at room temperature. After stirring for 1 hour, cyanuric chloride (7.0 g) was added at room temperature, followed by stirring for 3 hours. Ice water was added, followed by extraction w... | Cc1nc2ccccc2n1-c1nc(Cl)nc(Cl)n1 | null | 24.5 | null |
194,030 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | C([N:3]1[CH2:8][CH2:7][N:6]([OH:9])[CH2:5][CH2:4]1)=O.[ClH:10]>>[ClH:10].[ClH:10].[OH:9][N:6]1[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]1 | O=CN1CCN(O)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.33 | 3N Hydrochloric acid (50 ml) was added to 1-formyl-4-hydroxypiperazine (5.0 g) and the mixture was stirred at 77° to 87° C. for 20 minutes. After stirring, water was distilled off under reduced pressure to give a pale yellow residue, which was washed with ethanol and recrystallized from a mixed solvent of water-ethanol... | ON1CCNCC1 | null | null | null |
414,027 | ord_dataset-275344fd078b4340b89ca0b6e92beb95 | null | 1998-01-01T00:10:00 | true | C([O:3][C:4]([C:6]1([CH3:18])[C:11](=[O:12])[N:10]([CH3:13])[C@@H:9]2[CH2:14][CH2:15][CH2:16][CH2:17][C@H:8]2[O:7]1)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[CH3:18][C:6]1([C:4]([OH:5])=[O:3])[C:11](=[O:12])[N:10]([CH3:13])[C@@H:9]2[CH2:14][CH2:15][CH2:16][CH2:17][C@H:8]2[O:7]1 | CCOC(=O)C1(C)O[C@@H]2CCCC[C@H]2N(C)C1=O | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | trans-Ethyl-2,4-dimethyl-3-oxo-octahydro-2H-1,4-benzoxazine-2-carboxylate (180 mg, 0.71 mmoles) and 1N NaOH (1.1 ml, 1.1 mmoles) in dioxan (5 ml) were stirred for 20 hours. The solvent was evaporated, 1N HCl (11 ml, 11 mmoles) was added to the residue and the mixture was extracted with ethyl acetate (3×20 ml). The orga... | CN1C(=O)C(C)(C(=O)O)O[C@@H]2CCCC[C@H]21 | null | 70.7 | null |
1,584,692 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | Br[C:2]1[C:3]([F:22])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH:18]4[CH2:20][CH2:19]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:21]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([OH:33])([C:31]#[CH:32])[CH3:30]>>[CH:18]1([C:12]2[N:8]3[CH2:9][CH2:10][O:11][C:5]4[CH:4]=[C:3]([F:22])[C:2]([C:... | C#CC(C)(O)c1ccccn1 | NC(=O)c1nc2n(c1C1CC1)CCOc1cc(F)c(Br)cc1-2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 10-bromo-3-cyclopropyl-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with 2-(pyridin-2-yl)but-3-yn-2-ol via General Procedure E to yield 9.5 mg (16%) of (±)-3-cyclopropyl-9-fluoro-10-[3-hydroxy-3-(2-pyridyl)but-1-ynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide. | CC(O)(C#Cc1cc2c(cc1F)OCCn1c-2nc(C(N)=O)c1C1CC1)c1ccccn1 | null | 16 | null |
451,191 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | [I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([OH:20])=O)[N:9]=1.Cl.CN.C[CH2:25][N:26](CC)CC>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([NH:26][CH3:25])=[O:20])[N... | CCN(CC)CC | O=C(O)c1cc2ccccc2c(-c2ccccc2I)n1 | null | CN | Cl | 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 | 7 | To a mixture of 1-(2-iodophenyl)-3-isoquinolinecarboxylic acid (0.1868 g, 0.5 mmol), benzotriazol-1-yloxy-tris (demethylamino) phosphonium hexafluorophosphate (BOP) (0.2219 g, 0.5 mmol), Methylamine hydrochloride (0.1019 g, 1.5 mmol) in DMF (8 mL) was added Et3N (0.42 mL, 4.5 mmol). The resulting mixture was stirred un... | CNC(=O)c1cc2ccccc2c(-c2ccccc2I)n1 | null | 63.7 | null |
192,752 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | C[N:2]([CH3:16])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)=O.N[C:18]1[C:22]([C:23]#[N:24])=C[NH:20][N:19]=1>C(O)(=O)C>[N+:13]([C:9]1[CH:8]=[C:7]([C:5]2[N:20]3[N:19]=[CH:18][C:22]([C:23]#[N:24])=[C:16]3[N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=1)([O-:15])=[O:14] | N#Cc1c[nH]nc1N | CN(C)C=CC(=O)c1cccc([N+](=O)[O-])c1 | 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 | 25 | 16 | A mixture of 24.4 g of 3-dimethylamino-3'-nitroacrylophenone, 13.0 g of 3-aminopyrazole-4-carbonitrile and 120 ml of glacial acetic acid was heated at reflux for 7 hours, then was stirred at room temperature for 16 hours. The precipitate was collected, triturated with saturated aqueous sodium bicarbonate, filtered and ... | N#Cc1cnn2c(-c3cccc([N+](=O)[O-])c3)ccnc12 | null | null | null |
402,332 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3](OC)=[O:4].[CH3:11][NH:12][NH2:13]>CCOCC>[OH:4][C:3]1[N:12]([CH3:11])[N:13]=[C:1]([C:7]([O:9][CH3:10])=[O:8])[CH:2]=1 | COC(=O)C#CC(=O)OC | CNN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | -5 | 1 | 102.3 g (0.72 mol) Dimethyl acetylenedicarboxylate was added to 1000 ml ether and the mixture cooled to -5° C. in an ice-methanol bath. 33 g (0.72 mol) methylhydrazine in 100 ml ether was added dropwise at a rate that the inner temperature did not rise above 0° C. The mixture was stirred for one hour at 0° C., the prec... | COC(=O)c1cc(O)n(C)n1 | null | null | null |
783,759 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH:1]1([NH:7][CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:9]1([CH2:15][N:16]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[C:19](=[O:26])OC2=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>>[CH:1]1([N:7]([CH3:8])[C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH:16][CH2:15][CH:9]2[CH2:10][CH2:11][CH2:12][... | O=c1oc(=O)n(CC2CCCCC2)c2ccccc12 | CNC1CCCCC1 | null | null | null | null | null | null | null | 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 (0.3 g, 67%) was obtained as a orange solid from N-cyclohexyl-N-methylamine and 1-Cyclohexylmethyl-1H-benzo[d][1,3]oxazine-2,4-dione following the same procedure as described in Preparation 7. | CN(C(=O)c1ccccc1NCC1CCCCC1)C1CCCCC1 | null | 67 | null |
324,807 | ord_dataset-fc4cd2699fc04ecbb7c7c831849e6b22 | null | 1996-01-01T00:02:00 | true | [CH2:1]([C:6]1[CH2:7][CH:8]([CH2:17]O)[S:9][CH2:10][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:2][CH2:3][CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>C(Cl)Cl>[Br:39][CH2:17][CH:8]1[CH2:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH... | BrC(Br)(Br)Br | CCCCCC1=C(CCCCC)CC(CO)SC1 | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 14 | Part B. The alcohol from Part A above is dissolved in methylene chloride along with carbon tetrabromide, and cooled to 0° C. A methylene chloride solution of triphenylphosphine is added dropwise. The mixture is stirred for 14 hours, then evaporated and rapidly eluted through a plug ofsilica gel with an appropriate solv... | CCCCCC1=C(CCCCC)CC(CBr)SC1 | null | null | null |
1,208,455 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[N:7]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([Br:25])=[C:22]([OH:24])[CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([Br:25])=[C:22]([CH:23]=1)[O:24][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C... | Nc1ccc(Br)c(O)c1 | O=C(Nc1cn2nc(I)ccc2n1)C1CC1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 140 | 12 | To a solution of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (2.2 g, 6.7 mmol) in N,N-dimethylformamide (60 mL) were added 5-amino-2-bromophenol (1.9 g, 10 mmol) and potassium carbonate (1.8 g, 13 mmol), and the mixture was stirred at 140° C. for 12 hr. After cooling the mixture to room temperature, t... | Nc1ccc(Br)c(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)c1 | null | 30.4 | null |
1,273,367 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH:8]([C:11]([N:13]3[CH2:17][CH:16]([NH:18][CH3:19])[CH:15]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=4)[CH2:14]3)=[O:12])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:39])[C:36]([OH:38])=O)=[CH:31][CH:30]=1>>[CH:1]1([CH2:4][N:5]2... | CNC1CN(C(=O)C2CCN(CC3CC3)CC2)CC1c1ccc(Cl)c(Cl)c1 | CC(C(=O)O)c1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described for the synthesis of example 87 (step c), the title compound N-[(3RS,4SR)-1-(1-cyclopropylmethyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-2-(4-fluoro-phenyl)-N-methyl-propionamide was prepared from (1-cyclopropylmethyl-piperidin-4-yl)-[(3SR,4RS)-3-(3,4-dichlo... | CC(C(=O)N(C)C1CN(C(=O)C2CCN(CC3CC3)CC2)CC1c1ccc(Cl)c(Cl)c1)c1ccc(F)cc1 | null | null | null |
1,208,579 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [Si]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([NH2:26])=[O:25])=[C:21]([O:27][CH:28]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=4[C:37]([F:40])([F:39])[F:38])[CH3:29])[CH:20]=3)[C:12]=2[CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:36][C:33]1[C... | CC(Oc1cc(-n2cnc3cnc(CO[Si](C)(C)C(C)(C)C)cc32)sc1C(N)=O)c1ccc(F)cc1C(F)(F)F | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | 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 | 1.5 | A mixture of 1.48 g of 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-{-1-[4-fluoro-2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide in 25 ml THF is cooled to 0° C. At 0° C. 0.91 ml tetra-n-butylammonium fluoride (˜75% in H20) are added. The reaction mixture is allowed to warm to... | CC(Oc1cc(-n2cnc3cnc(CO)cc32)sc1C(N)=O)c1ccc(F)cc1C(F)(F)F | null | null | null |
1,698,633 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11]([O:13][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:12])=[CH:6][CH... | BrCc1ccccc1 | O=C(O)[C@@H]1C[C@@H]1c1ccc(O)cc1 | null | O=C([O-])O | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 40 | null | To a 100 mL RB flask fitted with magnetic stirrer was charged with 50 mL of acetone. To the stirred solvent was added (1R,2S)-2-(4-hydroxyphenyl)cyclopropanecarboxylic acid (0.51 g, 2.86 mmol). The reaction mixture was brought to 0° C., potassium bicarbonate (0.28 g, 2.8 mmol), stirred for 10 minutes, benzyl bromide (0... | O=C(OCc1ccccc1)[C@@H]1C[C@@H]1c1ccc(O)cc1 | null | 58.6 | null |
302,076 | ord_dataset-9ad0840101374618a7d5c4e4521c82d1 | null | 1994-01-01T00:12:00 | true | [C:1](=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]2[C:9]=1[CH2:10][CH2:11][C:12]2=[O:18].S(OC)(OC)(=O)=O>CC(C)=O>[F:7][C:8]1[CH:16]=[CH:15][C:14]([O:17][CH3:1])=[C:13]2[C:9]=1[CH2:10][CH2:11][C:12]2=[O:18] | O=C([O-])[O-] | O=C1CCc2c(F)ccc(O)c21 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | COS(=O)(=O)OC | null | null | null | null | null | null | null | null | null | null | null | In a nitrogen atmosphere, to 300 g powdered potassium carbonate in 1.5 1 of acetone is added 121 g II under stirring, followed by 83 ml of dimethyl sulphate. After heating to reflux for 2 hrs, the solvent is distilled off, water is added and the mixture refluxed for a further hour. Extraction with methylene chloride an... | COc1ccc(F)c2c1C(=O)CC2 | null | null | null |
1,377,945 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Cl:1][C:2]1[C:7]([NH:8]C(=O)OC(C)(C)C)=[C:6]([CH:16]=O)[CH:5]=[CH:4][N:3]=1.[C:18]1([CH2:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)... | CC(C)(C)OC(=O)NC1(c2ccc(C(=O)Cc3ccccc3)cc2)CCC1 | CC(C)(C)OC(=O)Nc1c(C=O)ccnc1Cl | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 120 | 15 | A mixture of tert-butyl (2-chloro-4-formylpyridin-3-yl)carbamate (7-3) (300 mg, 1.17 mmol), tert-butyl {1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamate (4-1) (427 mg, 1.17 mmol) and potassium carbonate (485 mg, 3.51 mmol) in DMF (10 mL) was stirred at 120° C. for 15 hours. The reaction mixture was cooled to room tempera... | CC(C)(C)OC(=O)NC1(c2ccc(-c3nc4c(Cl)nccc4cc3-c3ccccc3)cc2)CCC1 | null | null | null |
1,409,809 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | I[CH2:2][C@@H:3]([CH3:18])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:17].[CH2:19]([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[CH2:20][CH2:21][CH3:22]>CCCCCCC.CCOC(C)=O>[CH2:19]([CH:23]1[CH2:28][CH2:27][N:26]([CH2:2][C@@H:3]([CH3:18])[CH2:4][N:5]2[C:10]3[CH:11]=[C... | COc1ccc2c(c1)N(C[C@H](C)CI)C(=O)CO2 | CCCCC1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCCC | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | The compound (S)-4-(3-Iodo-2-methylpropyl)-6-methoxy-4H-benzo[1,4]oxazin-3-one (111MF36) (0.636 g, 1.77 mmol) and 4-butylpiperidine (0.226 g, 1.6 mmol) were mixed according to GP16. CC (SiO2; Heptane/EtOAc 4:1-4) and prep HPLC gave the title compound (111MF38) (0.245 g, 27%). 1H NMR (CDCl3) δ 6.89 (d, J=8.8 Hz, 1H), 6.... | CCCCC1CCN(C[C@@H](C)CN2C(=O)COc3ccc(OC)cc32)CC1 | null | 40.9 | null |
828,669 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41][CH2:42]O)[CH:35]=1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][S:52]([C:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[C:57]([O:63][CH3:64])[CH:56]=2)(=[O:54])=[O:53])=[C:47]([CH2:65][C:66]2[C:71]([F:72]... | COc1ccc(S(=O)(=O)Nc2ccc(Cl)cc2Cc2c(F)cccc2F)cc1OC | OCCCc1cccnc1 | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.25 | To 1.5 g of triphenylphosphine dissolved in 25 ml of THF is added 0.909 g of diisopropyl azodicarboxylate. After 15 minutes at room temperature, 0.61 g of 3-pyrid-3-ylpropan-1-ol is introduced and the mixture is left at 20° C. for 15 minutes. 1.36 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxybenzenesulfo... | COc1ccc(S(=O)(=O)N(CCCc2cccnc2)c2ccc(Cl)cc2Cc2c(F)cccc2F)cc1OC | null | null | null |
1,169,847 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1>>[F:15][C:14]([F:17])([F:16])[C:12]1[CH:11]=[C:10]([C:18]2[CH:23]=[CH:22][C:2... | OB(O)c1cccnc1 | FC(F)(F)c1ccc(-c2cc(C(F)(F)F)nc(-c3ccnc(Cl)c3)n2)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 was prepared from 2-(2-chloro-pyridin-4-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (example E.6) (0.202 g, 0.5 mmol) and commercially available 3-pyridineboronic acid (0.08 g, 0.65 mmol) according to the general procedure VI. Obtained as a white solid (0.013 g, 6%). MS (ISP) 447.0 ... | FC(F)(F)c1ccc(-c2cc(C(F)(F)F)nc(-c3ccnc(-c4cccnc4)c3)n2)cc1 | null | null | null |
1,391,434 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [S:1]1[C:5]([C:6]2[C:7]([NH2:26])=[N:8][CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:14][CH:13]=3)[N:11]=2)=[CH:4][CH:3]=[C:2]1[C:27]1[S:28][CH:29]=[CH:30][CH:31]=1.[Si:32]([O:39][C:40]1[CH:45]=[CH:44][C:43]([CH2:46][C:47](Cl)=[O:48])=[CH:42][CH:41]=... | CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)Cl)cc1 | CC(C)(C)[Si](C)(C)Oc1ccc(-c2cnc(N)c(-c3ccc(-c4cccs4)s3)n2)cc1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | c1ccncc1 | null | null | null | null | null | null | null | null | null | 50 | 20 | Under an argon atmosphere, to a mixture of 3-(2,2′-bithiophen-5-yl)-5-[4-(tert-butyldimethylsilyloxy)phenyl]pyrazin-2-amine (7m) (350 mg, 752 μmol) and 4-(dimethylamino)pyridine (15.0 mg, 123 μmol) dissolved in anhydrous pyridine (15 mL) was added 2-[4-(tert-butyl dimethylsilyloxy)phenyl]acetyl chloride (10) prepared a... | CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)Nc2ncc(-c3ccc(O[Si](C)(C)C(C)(C)C)cc3)nc2-c2ccc(-c3cccs3)s2)cc1 | null | null | null |
1,581,473 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | FC(F)(F)C([NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[C@H:9]([OH:17])[CH2:8][CH2:7]1)=O.[OH-].[Na+]>CO.O>[NH2:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[C@H:9]([OH:17])[CH2:8][CH2:7]1 | O=C(N[C@H]1CC[C@@H](O)c2ccc(F)cc21)C(F)(F)F | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 25 | 65 | To a solution of 2,2,2-trifluoro-N-((1S,4R)-7-fluoro-4-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetamide (synthesised in an analogous manner to that described in WO 2009/048474, which is incorporated herein by reference in its entirety) (2.31 g, 8.34 mmol) in MeOH (22.5 mL), was added a solution of sodium hydroxide... | N[C@H]1CC[C@@H](O)c2ccc(F)cc21 | null | 86 | null |
1,051,851 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | Cl.[CH2:2]([O:4][C:5](=[O:14])[CH:6]([NH:10][CH:11]1[CH2:13][CH2:12]1)[C:7](=[O:9])[CH3:8])[CH3:3].[N:15]1([C:21]2[CH:22]=[C:23]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=2)[C:24](O)=[O:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[CH2:2]([O:4][C:5](=[O... | O=C(O)c1cc(N2CCOCC2)cc(C(F)(F)F)c1 | CCOC(=O)C(NC1CC1)C(C)=O | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 3 | To 0.4 g (2 mmol) of 2-cyclopropylamino-3-oxo-butyric acid ethyl ester hydrochloride salt, 0.6 g (2 mmol) of 3-morpholin-4-yl-5-trifluoromethyl-benzoic acid, 0.4 g (2 mmol) of EDCI and 0.3 g (2 mmol) of HOBT was added 2 ml of DMF and 0.6 ml (4 mmol) of triethylamine. The mixture was stirred for 3 h after which time the... | CCOC(=O)C(C(C)=O)N(C(=O)c1cc(N2CCOCC2)cc(C(F)(F)F)c1)C1CC1 | null | 90.4 | null |
185,549 | ord_dataset-754e10d30fb249229e130865010ab25b | null | 1989-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[NH:10][C:9]2=[O:19])=[CH:4][C:3]=1[O:20][CH:21]([CH3:23])[CH3:22].S(OC)(O[CH3:28])(=O)=O.C(=O)(O)[O-].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:17])([F:18])[F:16])[N:10]=[C:9... | COS(=O)(=O)OC | CC(C)Oc1cc(-n2c(=O)cc(C(F)(F)F)[nH]c2=O)ccc1Cl | null | O=C([O-])O | [Na+] | 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 | using 3-(4-chloro-3-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione with dimethyl sulphate and sodium bicarbonate in acetone there is obtained 1-(4-chloro-3-isopropoxyphenyl)-2-methoxy-4-trifluoromethyl -6(1H)-pyrimidinone. m.p. 55°-58° C. | COc1nc(C(F)(F)F)cc(=O)n1-c1ccc(Cl)c(OC(C)C)c1 | null | null | null |
1,383,682 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [Br:1][C:2]1[C:3]([CH3:11])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.O.[NH4+].[Cl-]>CCO.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[CH3:11] | Cc1ncc([N+](=O)[O-])cc1Br | null | null | [Fe] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 75 | 2 | To a solution of 3-bromo-2-methyl-5-nitropyridine (2.3 g, 10.5 mmol) in EtOH (20 mL) was added water (40 mL), NH4Cl (2.25 g, 42 mmol) and iron powder (2.94 g, 52.5 mmol). The mixture was stirred at 75° C. for 2 hours. After the reaction mixture was cooled to room temperature, it was filtered through a celite pad. Organ... | Cc1ncc(N)cc1Br | null | 77.4 | null |
136,118 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | [NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]>C(O)C>[C:5]([NH:9][CH:8]=[N:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:8]2[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=2)[CH:11]=1)#[N:1] | N=C(N)Nc1nc(-c2cccc(N)c2)cs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 9.33 gm of 2-guanidino-4-(3-amino-phenyl)-thiazole and 3.93 gm of ethyl N-cyano-formamidate in 65 ml of ethanol was stirred at room temperature overnight. The crystalline product which separated out was collected by filtration, washed with cold ethanol and dried, yielding 9.2 gm of the title compound, mp.... | N#CNC=Nc1cccc(-c2csc(NC(=N)N)n2)c1 | null | 161.2 | null |
237,619 | ord_dataset-56e7a343b17a4d6da818127ceb19589d | null | 1991-01-01T00:11:00 | true | [C:1]([CH2:6][CH2:7][CH:8]1[C:13](=O)[CH2:12][CH2:11][CH2:10][C:9]1=[O:15])([O:3]CC)=O.[CH2:16]([NH2:18])[CH3:17]>>[CH2:16]([N:18]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9](=[O:15])[C:8]=2[CH2:7][CH2:6][C:1]1=[O:3])[CH3:17] | CCOC(=O)CCC1C(=O)CCCC1=O | CCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 21.2 g (0.1 mol) of 2-(2-carbethoxy-ethyl)-cyclohexan- 1,3-dione and 200 ml of 24% ethanolic ethylamine solution are heated to 180° C. in a stirred autoclave for 3 hours. The reaction solution is evaporated down using a rotary evaporator and the residue is chromatographed on a silica gel column with cyclohexane/ethyl a... | CCN1C(=O)CCC2=C1CCCC2=O | null | null | null |
1,712,578 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([C:16](=[O:20])[N:17]([CH3:19])[CH3:18])[C@@H:13]([OH:21])[CH2:12][N:11]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14](... | CN(C)C(=O)C1=C[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)OC(C)(C)C)C[C@@H]1O | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | 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 | (2S,5R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 133, 2.194 g, 5.29 mmol) in DCM (65 mL) was cooled in an ice-bath then Dess-Martin periodinane in DCM (26.5 mL, 7.94 mmol) was added and the reaction was stirred at rt overnight.... | CN(C)C(=O)C1=C[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)OC(C)(C)C)CC1=O | null | 48.1 | null |
1,544,595 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [NH2:1][C@@H:2]1[C:11]([CH3:13])([CH3:12])[C:10]2[CH:9]=[C:8]([C:14]([NH2:16])=[O:15])[CH:7]=[CH:6][C:5]=2[CH2:4][C@H:3]1[O:17][CH3:18].O=[CH:20][CH2:21][CH2:22][NH:23][C:24]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25].C(O)(C(F)(F)F)=O>>[CH:26]1([C:24]([NH:23][CH2:22][CH2:21][CH2:20][NH:1][C@@H:2]2[C:11](... | CO[C@@H]1Cc2ccc(C(N)=O)cc2C(C)(C)[C@H]1N | O=CCCNC(=O)C1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | Following the process of Example 11(c) using (6R,7R)-7-amino-6-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid amide and cyclohexanecarboxylic acid (3-oxo-propyl)-amide the TFA salt of the title compound was prepared. (m/z): [M+H]+ calcd for C24H37N3O3, 416.28; found, 416.5. | CO[C@@H]1Cc2ccc(C(N)=O)cc2C(C)(C)[C@H]1NCCCNC(=O)C1CCCCC1 | null | null | null |
716,262 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:12])[F:13])[CH:11]=3)[CH:7]=[CH:8]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | Ic1ccccc1 | FC(F)(F)c1ccc2cc[nH]c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by Procedure C and Scheme O using 6-(trifluoromethyl)-1H-indole and iodobenzene: ESMS m/e: 262.0 (M+H)+. | FC(F)(F)c1ccc2ccn(-c3ccccc3)c2c1 | null | null | null |
995,352 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | C(OC([N:8]1[C@H:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=3)=[CH:16][N:17]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.C(OCC)(=O)C.[ClH:33]>O1CCCC1>[ClH:33].[ClH:33].[NH2:8][C@H:12]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)=[CH:16][N:17]=1)[CH2:11][OH:10] | CC(C)(C)OC(=O)N1[C@H](c2ncc(-c3cccc(Br)n3)s2)COC1(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 90 | null | To a solution of (S)-4-[5-(6-bromopyridin-2-yl)thiazol-2-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (5.00 g, 11.4 mmol) obtained in Step 2 in tetrahydrofuran (30 ml) was added 4N hydrogen chloride-ethyl acetate solution (30 ml) and heated to reflux at 90° C. for 2 hours. After the reaction solution ... | N[C@@H](CO)c1ncc(-c2cccc(Br)n2)s1 | null | null | null |
1,760,651 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [F:1][CH2:2][CH:3]([OH:7])[C:4]([O-:6])=[O:5].[C:8]1([CH:14]([NH3+])C)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Br)C1C=CC=CC=1>CN(C=O)C.CCOC(C)=O>[F:1][CH2:2][CH:3]([OH:7])[C:4]([O:6][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5] | CC([NH3+])c1ccccc1 | O=C([O-])C(O)CF | null | BrCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 1-phenylethanaminium 3-fluoro-2-hydroxypropanoate (11-1) (0.14 g, 0.61 mmol) in DMF (1 mL) was added benzyl bromide (0.087 mL, 0.73 mmol). The mixture was stirred at room temperature overnight, diluted with EtOAc, washed with water and brine, dried over sodium sulfate, filtered, and concentrated. The r... | O=C(OCc1ccccc1)C(O)CF | null | null | null |
1,726,046 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [C:1]([O:8]CC)(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=O.CC(C)N=C=N[CH:16]([CH3:18])[CH3:17]>CN(C=O)C>[CH:17]1[CH:16]=[C:18]2[C:4]([CH:3]=[C:2]([C:1]([OH:8])=[O:7])[O:6][C:4]2=[CH:3][CH:2]=1)=[O:6] | CC(C)N=C=NC(C)C | CCOC(=O)CCC(=O)[O-] | 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 | null | null | LP-1 ctrl was synthesized by following Scheme 1 (FIG. 14). Rink SS resin was deprotected and loaded with monoethyl succinate (5 eq) and DIC (5 eq) in DMF for 2 hrs. The rest of the amino acids were added successively and the final product was purified by following the same methods described above. | O=C(O)c1cc(=O)c2ccccc2o1 | null | null | null |
1,138,423 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [Na:1].C(C1(CCO[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][S:24]([C:26]3[NH:30][C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[N:27]=3)=[O:25])[C:18]=2[CH3:35])OCC2(OCCO2)CO1)C.ClC1C=CC=C(C(OO)=O)C=1.[CH2:47]([C:49]1([CH2:56][CH3:57])[O:53][CH:52]([CH2:54][OH:55])[CH2:51][O:50]1)[CH3:48]>>[Na:1].[CH2:56]([C:49]1([CH2:47... | CCC1(CCOc2ccnc(CS(=O)c3nc4ccccc4[nH]3)c2C)OCC2(CO1)OCCO2 | CCC1(CC)OCC(CO)O1 | null | O=C(OO)c1cccc(Cl)c1 | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The same procedure as in the steps (4f) to (4j) of Example 4 (a reprecipitation operation was not performed in oxidation step with 3-chloroperbenzoic acid) was repeated using (2,2-diethyl-1,3-dioxolan-4-yl)methanol obtained in the step (65b) above to obtain the title compound (418 mg, total 14.3% yield) as a light yell... | CCC1(CC)OCC(COc2ccnc(CS(=O)c3nc4ccccc4[nH]3)c2C)O1 | null | 14.3 | null |
1,488,296 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([NH2:19])[CH:18]=3)=[O:12])=[CH:9][N:8]([C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])[C:6]=2[N:7]=1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33](O)=[O:34])=[N:30][CH:31]=1>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]([C:13]3[CH:18]=[C:... | O=C(O)Cc1ccc(Br)cn1 | CC(C)(CO)n1cc(C(=O)c2cncc(N)c2)c2cnc(N)nc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the method described for Example 34 at 50° C. using [2-amino-7-(2-hydroxy-1,1-dimethylethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl](5-aminopyridin-3-yl)methanone (Preparation 48) and (5-bromopyridin-2-yl)acetic acid to afford the title compound as a yellow solid in 60% yield, 75 m... | CC(C)(CO)n1cc(C(=O)c2cncc(NC(=O)Cc3ccc(Br)cn3)c2)c2cnc(N)nc21 | null | null | null |
455,812 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | [OH:1][N:2]=[C:3]([C:14]#[N:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1.[CH:16]([C:19]1[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:22]=[C:21]([CH:28]([CH3:30])[CH3:29])[C:20]=1[S:31](Cl)(=[O:33])=[O:32])([CH3:18])[CH3:17].C(N(CC)CC)C>C(#N)C>[CH:16]([C:19]1[CH:24]=[C:23]([CH:25]([CH3:26])... | CC(C)c1cc(C(C)C)c(S(=O)(=O)Cl)c(C(C)C)c1 | COc1ccc(C(C#N)=NO)cc1OC | null | null | null | 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 | As described under 1.2, 8.25 g (0.04 mol) of α-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted with 13.3 g (0.044 mol) of 2,4,6-tris(isopropyl)benzenesulfonyl chloride in the presence of triethylamine. After recrystallisation of the crude product from ethyl acetate/-hexane, 14.25 g (75%) of α-(2,4,6-tris(isopropyl... | COc1ccc(C(C#N)=NOS(=O)(=O)c2c(C(C)C)cc(C(C)C)cc2C(C)C)cc1OC | null | null | null |
1,692,372 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[CH:5][CH:4]=1.[OH-].[Na+]>CO.Cl>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1 | CSc1ccc(NC(=O)CC(=O)OCc2ccccc2)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 40 | 2 | Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate (150 mg, 0.476 mmol) was dissolved in MeOH (1.5 ml). NaOH 1M (500 μl) was added, and the reaction was stirred at 40° C. for 2 hours to achieve completion. The reaction mixture was diluted with HCl 1N and extracted with EtOAc. The organic phase was washed with HCl 1N ... | CSc1ccc(NC(=O)CC(=O)O)cc1 | null | 83.9 | null |
434,082 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | Cl[C:2]1[CH:13]=[CH:12][C:5]([C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].C(=O)([O-])[O-].[K+].[K+].Cl>CN1CCCC1=O>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[CH:13]=[CH:12][C:5]([C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])=... | Nc1cccc(Br)c1 | CC(C)OC(=O)c1ccc(Cl)c([N+](=O)[O-])c1 | null | Cl | O=C([O-])[O-] | [K+] | 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 | 150 | null | A mixture of i-propyl 4-chloro-3-nitrobenzoate (25.88 g, 0.11 mol), 3-bromoaniline (17.36 ml, 0.16 mol) and potassium carbonate (14.63 g, 0.11 mol) in N-methyl-2-pyrrolidone (25 ml) is heated to 150° C. for 3 days. After cooling the mixture is poured into diluted hydrochloric acid (300 ml, 1 M). The precipitate is filt... | CC(C)OC(=O)c1ccc(Nc2cccc(Br)c2)c([N+](=O)[O-])c1 | null | 62.9 | null |
649,513 | ord_dataset-5d77a731aa10488794c824ad12021f57 | null | 2004-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[CH3:23].[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:... | COc1cc2ncnc(Oc3ccc(N)cc3C)c2cc1OC | O=C=Nc1ccc(F)cc1 | 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 | null | null | 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-3-methyl-aniline (50 mg) was dissolved in chloroform (3 ml), and p-fluorophenyl isocyanate (22 μl ) was then added to the solution. The mixture was heated under reflux overnight. The precipitated crystal was collected by filtration and was washed to give 42 mg (yield 58%) of the ti... | COc1cc2ncnc(Oc3ccc(NC(=O)Nc4ccc(F)cc4)cc3C)c2cc1OC | null | 58 | null |
414,642 | ord_dataset-1cb9d78632144c5f8acfc3e9ff388678 | null | 1998-01-01T00:11:00 | true | [OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][CH:3]=1.[CH3:9][C:10]([CH3:12])=O>O>[CH2:9]([O:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][CH:3]=1)[C:10]1[CH:12]=[CH:6][CH:7]=[CH:2][CH:3]=1 | O=c1ccocc1O | CC(C)=O | 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 | 3-Benzyloxy-4-pyrone is prepared from 3-hydroxy-4-pyrone as described by Spenser et al, Canadian Journal of Chemistry, 1962, 40, 1377 and has m.p. 82°-85° C. A mixture of this compound (1 g) and ethylenediamime (0.37 g) in water (12 ml) is heated under reflux for 1 hour. The reaction mixture is evaporated to dryness an... | O=c1ccocc1OCc1ccccc1 | null | 34 | null |
1,104,683 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][OH:15]>>[NH2:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][C:4]=1[NH:11][CH2:12][CH2:13][CH2:14][OH:15] | N#Cc1ccc(Cl)cc1F | NCCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is synthesized by coupling followed by reduction of 4-chloro-2-fluoro-benzonitrile and 3-amino-propanol analogously to the preparation of Intermediate 113.1. colorless oil; ES-MS: M−=213.1; HPLC: AtRet=2.27 min. | NCc1ccc(Cl)cc1NCCCO | null | null | null |
1,282,330 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[O:30])=[C:4]([OH:32])[CH:3]=1.FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[C... | O=C1N(C(c2ccccc2)c2ccccc2)c2ccccc2C1(O)c1ccc(Br)cc1O | null | null | CC[SiH](CC)CC | 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 | 64 | To an ice cold stirred solution of 3-(4-bromo-2-hydroxyphenyl)-1-(diphenylmethyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one (13.1 g, 27.1 mmol) in triethylsilane (25.0 mL) was added trifluoroacetic acid (25.0 mL). The solution was stirred at ambient temperature for 64 h, then concentrated in vacuo to dryness. Recrystallizat... | O=C1C(c2ccc(Br)cc2O)c2ccccc2N1C(c1ccccc1)c1ccccc1 | null | 79.2 | null |
1,424,266 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:5][CH2:6]S(C)=O>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[CH:5]=[CH2:6] | COC(=O)[C@H](CCS(C)=O)NC(=O)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | Sulfoxide 60 (5.69 g, 18.2 mmol) was placed in a round bottomed flask in a kugelrohr. This was directly connected to a low vacuum diaphragm pump and heated/distilled at 140° C. The distillate was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a colourless oil, ... | C=C[C@H](NC(=O)OCc1ccccc1)C(=O)OC | null | null | null |
1,308,040 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][CH:24]([N:27]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:37])[C:25]#[CH:26].C(N(CC)CC)C>C(#N)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=... | Brc1ccc(Oc2ccc(OCc3ccccc3)nc2)cc1 | C#CC(C)N1C(=O)c2ccccc2C1=O | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | I[Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC#N | null | null | null | null | null | null | null | null | null | 100 | 0.5 | 2-Benzyloxy-5-(4-bromophenoxy)pyridine (826 mg, 2.32 mmol) and 2-(1-methylprop-2-ynyl)isoindole-1,3-dione (693 mg, 3.48 mmol) were dissolved in anhydrous acetonitrile under argon and admixed with triethylamine (2.78 ml, 19.94 mmol), copper iodide (22.1 mg, 0.116 mmol) and bis(triphenylphosphine)palladium(II) chloride (... | CC(C#Cc1ccc(Oc2ccc(OCc3ccccc3)nc2)cc1)N1C(=O)c2ccccc2C1=O | null | null | null |
522,344 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | I[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:12]/[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)/[C:5](=[O:11])[NH:6]2.C([O-])([O-])=O.[Na+].[Na+].O.[NH2:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=... | Nc1cccc(B(O)O)c1 | O=C1Nc2cccc(I)c2/C1=C/c1ccc[nH]1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | O | null | null | null | null | null | null | null | null | null | 100 | null | A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (500 mg, 1.49 mmol) (Starting Material 1), 2M aqueous Na2CO3 solution (1.49 mL, 2.98 mmol), (Ph3P)4Pd (86 mg, 0.074 mmol) (Aldrich), and 3-aminophenylboronic acid monohydrate (253 mg, 1.63 mmol) (Lancaster) in 10 mL of a 3:1 mixture of 1,... | Nc1cccc(-c2cccc3c2/C(=C/c2ccc[nH]2)C(=O)N3)c1 | null | 91.3 | null |
1,087,424 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[NH:13][CH:12]=[CH:11]2.Br[CH2:20][CH:21]1[CH2:23][CH2:22]1>O>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:20][CH:21]1[CH2:23][CH2:22]1)[CH:12]=[CH:11]2 | O=c1[nH]ccc2cc(Br)ccc12 | BrCC1CC1 | null | O=C([O-])[O-] | [Cs+] | 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 | 50 | null | Cesium carbonate (2.62 g), intermediate 1 (1.5 g) and (bromomethyl)cyclopropane (0.8 mL) were stirred and heated at 50° C. for 4 hours. The mixture was allowed to cool then poured into water and extracted with ethyl acetate. The organic extracts were combined dried and evaporated under reduced pressure. The residue was... | O=c1c2ccc(Br)cc2ccn1CC1CC1 | null | null | null |
966,185 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | Br[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[C:14]([F:17])([F:16])[F:15].C1(C)C=CC=CC=1.[P:25]([O:30]C)([O:28][CH3:29])[O:26][CH3:27]>>[CH3:27][O:26][P:25]([CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[C:14]([F:17])([F:16])[F:15])([O:28][CH3... | CCOC(=O)c1ccc(CBr)c(C(F)(F)F)c1 | COP(OC)OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 6.20 g of ethyl 4-(bromomethyl)-3-trifluoromethylbenzoate (Reference Example 2 (step 2)) was dissolved in 12 ml of trimethyl phosphite and the mixture was heated at reflux for 4 hours under an argon atmosphere. After the completion of the reaction, the operation of adding of toluene to the residue, followed by azeotrop... | CCOC(=O)c1ccc(CP(=O)(OC)OC)c(C(F)(F)F)c1 | null | null | null |
787,624 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:31][C:28]([F:29])([F:30])[O:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH:... | FC(F)(F)Oc1ccc(OC2CCN(c3ccc(OC4CCCCO4)cc3)CC2)cc1 | null | null | Cc1ccc(S(=O)(=O)[O-])cc1 | c1cc[nH+]cc1 | 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 | 70 | 24 | A mixture of 1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenoxy)piperidine (30.1 g, 68.8 mmol) prepared in Reference Example 191 and pyridinium p-toluene sulfonate (5.2 g, 20.6 mmol) in ethanol (450 ml) was stirred at 70° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, and... | Oc1ccc(N2CCC(Oc3ccc(OC(F)(F)F)cc3)CC2)cc1 | null | 94.2 | null |
1,658,266 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].C([N:15]1[CH2:24][CH2:23][C:22]2[C:17](=[N:18][C:19]([N:29]3[CH2:34][CH2:33][CH:32]([O:35][C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=4[F:43])[CH2:31][CH2:30]3)=[C:20]([NH:25][CH:26]([CH3:28])[CH3:27])[N:21]=2)[CH:16]1[CH3:44])C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[F:... | CC(C)Nc1nc2c(nc1N1CCC(Oc3ccc(F)cc3F)CC1)C(C)N(Cc1ccccc1)CC2 | null | null | [Pd+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | A solution of 6-benzyl-3-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-N-isopropyl-5-methyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (150 mg, 0.241 mmol) and Pd(OH)2 on carbon (16.9 mg, 0.024 mmol) in THF (1.21 mL) was purged and placed under hydrogen atmosphere (balloon) overnight. The mixture was then filte... | CC(C)Nc1nc2c(nc1N1CCC(Oc3ccc(F)cc3F)CC1)C(C)NCC2 | null | null | null |
1,750,028 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [F:1][C:2]1([F:25])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17](Cl)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.Cl.Cl.[N:37]1([CH:42]2[CH2:46][CH2:45][NH:44][CH2:43]2)[CH2:41][CH2:40][CH2:39][CH2:38]1>>[F:1][C:2]1([F:25])[CH2:7][CH2:6][C:5... | O=C(NCC1(O)CCC(F)(F)CC1)c1c(Cl)ccc2nc(Cl)ccc12 | C1CCN(C2CCNC2)C1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized according to the procedure described in example 1 using 2,6-dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxycyclohexylmethyl)-amide, DIPEA and 3-pyrrolidinyl-pyrrolidine dihydrochloride. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (1H), 7.48 (2H), 6.69 (1H), 4.59 (s, 1H), 3.89 (m... | O=C(NCC1(O)CCC(F)(F)CC1)c1c(Cl)ccc2nc(N3CCC(N4CCCC4)C3)ccc12 | null | null | null |
1,564,546 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [NH2:1][CH2:2][CH:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)[OH:4].[Cl:15][CH2:16][C:17](Cl)=[O:18].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:15][CH2:16][C:17]([NH:1][CH2:2][CH:3]([OH:4])[C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)=[O:18] | Cn1ncc2ccc(C(O)CN)cc21 | O=C(Cl)CCl | null | null | null | 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 | 2 | To the crude material 2-amino-1-(1-methyl-1H-indazol-6-yl)ethanol (390.8 mg, ˜50%, ˜1 mmol)in DMF was then added 2-chloroacetyl chloride (138.7 mg, 1.2 mmol) and iPr2NEt (0.347 mL, 2 mmol). The resulting mixture was stirred at room temperature for 2 hr. The mixture was then taken into partition between EtOAc and brine.... | Cn1ncc2ccc(C(O)CNC(=O)CCl)cc21 | null | null | null |
314,813 | ord_dataset-bd998d3fe946475e835418aaf647c00d | null | 1995-01-01T00:08:00 | true | [NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:14]=[N:15][N:16]([CH3:22])[C:17]=3[NH:18]C(=O)C)[CH:8]=2)[C:5]2[CH:23]=[CH:24][CH:25]=[CH:26][C:4]=2[N:3]=1.[ClH:27]>>[ClH:27].[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:14]=[N:15][N:16]([CH3:22])[C:17]=3[NH2:18])[CH:8]=2)[C:5]2[CH:2... | CC(=O)Nc1c(-c2cccc(-n3c(N)nc4ccccc43)c2)cnn1C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-Amino-1-[3-(5-amino-1-methyl-4-pyrazolyl)phenyl]benzimidazole hydrochloride was prepared from 2-amino-1-[3-(5-acetamido-1-methyl-4-pyrazolyl)phenyl]benzimidazole by hydrolysis with 25% refluxing hydrochloric acid. mp 190°-193° C. | Cn1ncc(-c2cccc(-n3c(N)nc4ccccc43)c2)c1N | null | null | null |
213,547 | ord_dataset-b67d30cd146f49dcbf24faee022f1a09 | null | 1990-01-01T00:08:00 | true | [C:1]([O:7][CH2:8][CH2:9][S:10][C:11](=[O:13])[CH3:12])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].C([O-])(=O)C.[NH2+]1CCCCC1.O>C1C=CC=CC=1>[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[C:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:... | CC(=O)CC(=O)OCCSC(C)=O | O=Cc1cccc([N+](=O)[O-])c1 | null | C1CC[NH2+]CC1 | CC(=O)[O-] | 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 | null | null | A solution of 7.0 g of 2-acetylthioethyl acetoacetate, 5.14 g of 3-nitrobenzaldehyde and 0.99 g of piperidinium acetate in 100 ml of benzene was heated at reflux under azeotropic dehydration conditions for 2 hours. The reaction mixture was poured into water and extracted with benzene, and the extract was washed with wa... | CC(=O)SCCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O | null | 85.7 | null |
1,137,450 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9](Cl)(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1.[NH2:14][C:15]1[S:16][CH:17]=[CH:18][N:19]=1.N1C=CC=CC=1>>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1 | Nc1nccs1 | O=S(=O)(Cl)c1cc(F)c(Br)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 216 | 4-BROMO-2,5-DIFLUOROBENZENESULFONYL CHLORIDE (10.0 g, 0.0345 mol) and 2-AMINOTHIAZOLE (3.80 g, 0.0379 mol) were mixed in Pyridine (40 mL, 0.5 mol). The reaction was allowed to stir at room temperature for 9 days. The reaction was concentrated in vacuo to a total volume of approximately 40 mL. The residue was triturated... | O=S(=O)(Nc1nccs1)c1cc(F)c(Br)cc1F | null | 21.7 | null |
432,035 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[OH:15][C:16]1([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:32][CH2:33][CH2:34][CH3:35])[CH:28]=3)[CH:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1]... | CCCOc1ccc2cc(C3(O)CCNCC3)ccc2c1 | c1cc(OC[C@@H]2CO2)c2cc[nH]c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Beginning with 0.199 gm (1.1 mMol) (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 0.300 gm (1.1 mMol) 4-hydroxy-4-(6-propoxynaphth-2-yl)piperidine, 0.289 gm (60%) of the title compound were recovered as an off-white solid by the procedure described in Example 9. | CCCOc1ccc2cc(C3(O)CCN(C[C@H](O)COc4cccc5[nH]ccc45)CC3)ccc2c1 | null | 55.4 | null |
1,074,709 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([S:13](=[O:16])(=[O:15])[NH2:14])=[C:6]([CH:12]=1)[CH2:7][NH:8]C(=O)C.[ClH:17]>C(O)C>[ClH:17].[NH2:8][CH2:7][C:6]1[CH:12]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[S:13]([NH2:14])(=[O:16])=[O:15] | CC(=O)NCc1cc(F)ccc1S(N)(=O)=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | (Step 3) To a solution of N-(5-fluoro-2-sulfamoylbenzyl)acetamide obtained in Step 2 (2.7 g) in ethanol (20 ml) was added hydrochloric acid (10 ml) at room temperature, and the mixture was stirred with heating under reflux for 3 hr, and then overnight at 80° C. The solvent was evaporated under reduced pressure. The res... | NCc1cc(F)ccc1S(N)(=O)=O | null | null | null |
1,690,354 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [NH2:1][C:2]([C:4]1([CH3:17])[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1)=[O:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[CH3:17][C:4]1([C:2]([NH2:1])=[O:3])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1 | CC(C)(C)OC(=O)N1CCC(C)(C(N)=O)CC1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | 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 | 80 | 0.75 | A 500-mL three-neck round bottom flask was equipped with an overhead mechanical paddle stirrer, thermocouple with N2-inlet, and reflux condenser that was vented to the atmosphere. The reactor was charged with the product of Example 9 (45.68 g, 188.5 mmol), p-toluenesulfonic acid monohydrate (46.67 g, 2453 mmol, 1.3 equ... | CC1(C(N)=O)CCNCC1 | null | null | null |
1,657,544 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Br:1][C:2]1[N:3]=[C:4]([C:9]#[C:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([NH2:8])=[N:6][CH:7]=1.N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22]>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([C:9]#[C:10][Si:11]([CH3:13])([CH3:12])[CH3:14])[C:5]([NH:8][C:21](=[O:23])[CH3:22])=[N:6][CH:7]=1 | C[Si](C)(C)C#Cc1nc(Br)cnc1N | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 48 | To a solution of 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine (5.0 g, 19 mmol) and pyridine (3.8 mL, 46 mmol) in anhydrous THF (75 mL) was added acetyl chloride (1.6 mL, 23 mmol) in a drop-wise manner. After stirring for 48 hr at rt, additional acetyl chloride (0.4 mL, 6 mmol) was added and the mixture was stirre... | CC(=O)Nc1ncc(Br)nc1C#C[Si](C)(C)C | null | 30.3 | null |
521,560 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [OH-].[K+].[CH2:3]([O:10][C@@H:11]([CH3:17])[CH2:12][C:13]([O:15]C)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO>O>[CH2:3]([O:10][C@@H:11]([CH3:17])[CH2:12][C:13]([OH:15])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1 | COC(=O)C[C@H](C)OCc1ccccc1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 8.73 g of potassium hydroxide in 140 mL of cold water was dissolved methyl (S)-3-benzyloxybutyrate (18) (24.21 g). The solution was stirred in an ice bath for one hour and at room temperature for one hour. Methanol was added to give a clear solution and the reaction was stirred overnight. | C[C@@H](CC(=O)O)OCc1ccccc1 | null | null | null |
348,350 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | [NH2:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:3]1.[C:15]([NH:25][CH2:26][C:27](O)=[O:28])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C=O>[C:19]1([CH2:18][O:17][C:15](=[O:16])[NH:25][CH2:26][C:27]([NH:1][N:2]... | O=C(O)CNC(=O)OCc1ccccc1 | Nn1ccc(C(=O)c2ccccc2)c1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of (1-amino-1H-pyrrol-3-yl)phenylmethanone (5.96 g) and N-carbobenzyloxyglycine (6.69 g) in 70 ml of anhydrous DCM and 30 ml of anhydrous dimethylformamide was added DCC (7.22 g). The reaction mixture was stirred at room temperature for 4 hours and filtered. The filter cake was washed with ethyl acetate, ... | O=C(CNC(=O)OCc1ccccc1)Nn1ccc(C(=O)c2ccccc2)c1 | null | null | null |
766,093 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12](O)=[O:13])[CH:7]=[CH:8][CH:9]=1.C(Cl)(=O)C(Cl)=O.[NH3:23]>C1COCC1.CN(C)C=O>[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([NH2:23])=[O:13])[CH:7]=[CH:8][CH:9]=1 | O=C(O)C=Cc1cccc(OC(F)(F)F)c1 | N | null | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 3 | To a suspension of 3-(3-trifluoromethoxy-phenyl)-acrylic acid (2.21 g, 9.53 mmol) in THF (15 ml) and N,N-dimethyl formamide (0.2 ml) a solution oxalyl chloride (2.42 g, 19.06 mmol) was added dropwise at 0° C. within 45 min. Stirring was continued at 0–5° C. for 30 min. and 3 h at room temperature thereafter. The result... | NC(=O)C=Cc1cccc(OC(F)(F)F)c1 | null | 45 | null |
432,129 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=4[F:26])[CH2:14][CH2:13]3)[N:10]=2)[CH:7]=1.[OH-].[Na+].C([OH:33])(C)(C)C>OO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]4... | N#Cc1ccc(N2CCN(Cc3cn4cc(Cl)ccc4n3)CC2)c(F)c1 | CC(C)(C)O | null | OO | [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 | 90 | null | A mixture of 4-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]-3-fluorobenzonitrile (Example 38; 0.298 g), pulverized NaOH (0.159 g), tert-butanol (3 mL), and 5 drops of 30% hydrogen peroxide in water is heated at 90° C. for 5.5 h. The mixture is then concentrated under reduced pressure and the resulting... | NC(=O)c1ccc(N2CCN(Cc3cn4cc(Cl)ccc4n3)CC2)c(F)c1 | null | null | null |
756,501 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [C:1]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[OH:16])[C:9]([O:11][CH3:12])=[O:10])(=O)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.Cl.[NH2:24][OH:25]>C(O)C>[OH:16][C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1/[C:1](=[N:24]/[OH:25])/[CH2:2][CH2:3][CH3:4] | CCCC(=O)c1cc(C(=O)OC)ccc1O | NO | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | A stirred solution of methyl 3-butyryl-4-hydroxybenzoate, pyridine (3.7 mL, 46 mmol), and hydroxylamine hydrochloride (3.55 g, 51 mmol) in ethanol (30 mL) was heated reflux for 2 h. The mixture was concentrated under reduced pressure and partitioned between water and ethyl acetate. The organic layer was washed with 1 N... | CCC/C(=N\O)c1cc(C(=O)OC)ccc1O | null | null | null |
1,311,050 | 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]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[Cl:24][C:25]1[C:26]([NH:40][CH3:41])=[N:27][CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=1>>[Cl:24][C:25]1[CH:30]=[C:29]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:... | CNc1ncc(B2OC(C)(C)C(C)(C)O2)cc1Cl | Cc1nn(C)cc1-n1c(=O)n(C)c2cnc3ccc(Br)cc3c21 | null | null | null | null | null | null | null | 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-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A, 0.107 mmol) and [3-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-methyl-amine (stage 146.1.1) to g... | CNc1ncc(-c2ccc3ncc4c(c3c2)n(-c2cn(C)nc2C)c(=O)n4C)cc1Cl | null | null | null |
901,282 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:23]=[C:22]3[C:14]([N:15]4[C:20](=[CH:21]3)[C:19](=[O:24])[NH:18][CH2:17][CH2:16]4)=[N:13][CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].FC(F)(F)S(O[CH2:31][C:32]([F:35])([F:34])[F:33])(=O)=O.[H-].[Na+]>>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([O:10][C:11]2[CH:23]=[C:22]3[C:14]([... | CC(C)N1CCC(Oc2cnc3c(c2)cc2n3CCNC2=O)CC1 | O=S(=O)(OCC(F)(F)F)C(F)(F)F | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized in analogy to example 17, from 7-(1-isopropyl-piperidin-4-yloxy)-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one (example 84), 2,2,2-trifluoroethyl trifluoromethanesulfonate and sodium hydride, to give the desired product as a colorless solid (42%). | CC(C)N1CCC(Oc2cnc3c(c2)cc2n3CCN(CC(F)(F)F)C2=O)CC1 | null | 42 | null |
773,304 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Cl[CH2:16][CH2:17][CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=2)[NH:21][CH:20]=1>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][C:19]2[C:2... | Clc1cccc(N2CCNCC2)c1Cl | Fc1ccc2[nH]cc(CCCCl)c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | from 1-(2,3-dichlorophenyl)piperazine and 3-(3-chloropropyl)-5-fluoro-1H-indole. Mp 147–148° C. 1H NMR (DMSO-d6): 1.75–1.85 (m, 2H); 2.30–2.45 (t, 2H); 2.45–2.60 (m, 2H); 2.70 (t, 2H); 3.00 (b s, 4H); 3.35 (b s, 2H); 6.85–6.95 (m, 1H); 7.05–7.15 (m, 1H); 7.20 (s, 1H); 7.20–7.35 (m, 4H); 10.85 (b s, 1H). Ms m/z: 406 (MH... | Fc1ccc2[nH]cc(CCCN3CCN(c4cccc(Cl)c4Cl)CC3)c2c1 | null | null | null |
140,339 | ord_dataset-a2a0fbbcd49a46ffaa432d7ceae8a506 | null | 1986-01-01T00:02:00 | true | [CH3:1][S:2]([N:5]=[C:6](SC)[S:7][CH3:8])(=[O:4])=[O:3].[CH3:11][NH2:12]>C(O)C>[CH3:11][NH:12][C:6](=[N:5][S:2]([CH3:1])(=[O:4])=[O:3])[S:7][CH3:8] | CN | CSC(=NS(C)(=O)=O)SC | 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 | 53 | 8 | A mixture of N-methylsulphonyl-bis(methylthio)methanimine (188 g) and ethanol (760 ml) was stirred and warmed to 53° C. and the resulting solution was treated dropwise at 45° C. with a solution of methylamine in ethanol (33% w/w; 115 ml) during 2 hours. The solution was then stirred at room temperature for 7 hours and ... | CNC(=NS(C)(=O)=O)SC | null | null | null |
440,328 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-][CH2:10][CH3:11].[Na+]>C1COCC1>[C:2]1([CH:10]=[CH:11][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | CC[O-] | O=Cc1ccccc1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a mixture of 50 mg (0.47 mmol) benzaldehyde and 100 mg (0.047 mmol) Rink amide resin bound compound 1 in 5 mL THF, 12 μL 2M sodium ethoxide was added. It was shaken at room temperature for 2 hours. The resulting Resin bound compound 2 was collected in a 3 mL filtering column and washed with water (3×2 mL), DMF (2×2 ... | O=C(C=Cc1ccccc1)c1ccccc1 | null | null | null |
1,679,312 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | CN([SiH3])[Si:3]([CH3:6])(C)[CH3:4].[F:8][C:9]([F:22])([F:21])[S:10]([O:13]S(C(F)(F)F)(=O)=O)(=[O:12])=[O:11]>>[F:8][C:9]([F:22])([F:21])[S:10]([O:13][SiH:3]([CH3:6])[CH3:4])(=[O:12])=[O:11] | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | CN([SiH3])[Si](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 | Additionally, for example when mixing tetramethyldisilazane as the silicon compound B and trifluoromethanesulfonic anhydride as the acid B, the trifluoromethanesulfonic anhydride is rapidly reacted to form dimethylsilyl trifluoromethanesulfonate as the acid A. | C[SiH](C)OS(=O)(=O)C(F)(F)F | null | null | null |
155,321 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | Br[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]([CH3:20])[CH2:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:9][CH:8]=1)=[O:5].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)CC>[CH2:21]([NH:28][CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]([CH3:20])[CH2:15][C:1... | CC1CC(=O)NN=C1c1ccc(NC(=O)CCBr)cc1 | NCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCO | null | null | null | null | null | null | null | null | null | null | null | 2 | A suspension of 6-[4-(3-bromopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (120 g, 0.355 mol) and benzylamine (152 g, 1.47 mol) in n-propanol (800 ml) was stirred under reflux for 16 hours. The reaction mixture was filtered whilst hot and white solid was collected, which was washed with ether to remove e... | CC1CC(=O)NN=C1c1ccc(NC(=O)CCNCc2ccccc2)cc1 | null | 88.1 | null |
1,723,865 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH3:1][C:2]1[C:3](=[O:19])[N:4]([CH2:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[C:5](SC)=[N:6][N:7]=1.[NH:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21]1>>[C:13]([C:12]1[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=1[CH2:10][N:4]1[C:3](=[O:19])[... | CSc1nnc(C)c(=O)n1Cc1ccccc1C#N | CC(C)(C)OC(=O)N[C@@H]1CCCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 130 | 0.08 | The mixture of 2-((6-methyl-3-(methylthio)-5-oxo-1,2,4-triazin-4(5H)-yl)methyl)benzonitrile (6, 68 mg, 0.25 mmol) and (R)-tert-butyl piperidin-3-ylcarbamate (60 mg, 0.30 mmol) was ground for 5 min and then heated in a tube under nitrogen atmosphere at 130° C. for 13 h. The mixture was separated by silica gel column, an... | Cc1nnc(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)n(Cc2ccccc2C#N)c1=O | null | null | null |
469,833 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:12])[C:10]=1O)[C:5]([OH:7])=[O:6].[CH3:13][Si](C=[N+]=[N-])(C)C.S([O-])([O-])(=O)=O.[Mg+2]>CCOCC.CO>[CH3:13][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:10]=[C:9]([CH3:12])[CH:8]=1 | Cc1cc(C(=O)O)cc(C)c1O | C[Si](C)(C)C=[N+]=[N-] | null | O=S(=O)([O-])[O-] | [Mg+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A solution of 3,5-dimethyl-4-hydroxybenzoic acid (1.0 g) in ether (5 mL) and methanol(5 mL) was treated with excess trimethylsilyldiazomethane. After stirring 30 min at room temperature the reaction was treated with magnesium sulfate, filtered and concentrated to a brown solid. The title compound was obtained by purifi... | COC(=O)c1cc(C)cc(C)c1 | null | null | null |
887,189 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [NH2:1][C:2](=[O:36])[CH:3]([CH3:35])[O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20]C(=O)OC(C)(C)C)=[C:8]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[F:34].Cl>O1CCOCC1>[NH2:20][CH2:19][C:9]1[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[N:11][C:12]2[C... | CC(C)Cc1nc2ccc(OC(C)C(N)=O)cc2c(-c2ccccc2F)c1CNC(=O)OC(C)(C)C | 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 | 0.5 | To tert-butyl [6-(2-amino-1-methyl-2-oxoethoxy)-4-(2-fluorophenyl)-2-isobutylquinolin-3-yl]methylcarbamate (0.12 g, 0.24 mmol) was added 4N solution of hydrogen chloride in 1,4-dioxane (5 ml) and the mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned between ethyl acetate-isopropan... | CC(C)Cc1nc2ccc(OC(C)C(N)=O)cc2c(-c2ccccc2F)c1CN | null | 73.8 | null |
1,024,110 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:13]=1)([O-])=O>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:13]=1 | COC(=O)c1cc([N+](=O)[O-])cc2c1OCCO2 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 18 | Methyl 7-nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylate (5.6 g, 23.4 mmol) and palladium on carbon (250 mg, 30 wt. %) were suspended in ethyl acetate (200 mL). The reaction vessel was evacuated and then immediately filled with hydrogen gas. This deoxygenation process was repeated three times at atmospheric pressure. ... | COC(=O)c1cc(N)cc2c1OCCO2 | null | 99.9 | null |
1,687,578 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [F:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:13]=[C:12]([CH3:23])[C:11]=2[O:24][CH3:25])=[C:6]([F:26])[CH:5]=[CH:4][C:3]=1[OH:27].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CC(C)=O.O>[F:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[C... | CCOC(=O)CBr | COc1c(C)cc(-c2cccc(F)c2)cc1CNc1c(F)ccc(O)c1F | null | O=C([O-])[O-] | [Cs+] | 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 | 25 | 0.5 | To a stirred solution of 2,4-difluoro-3-[[5-(3-fluorophenyl)-2-methoxy-3-methyl-phenyl]methylamino]phenol (47 mg, 0.13 mmol, 1.0 eq) in acetone (5 mL) was added Cs2CO3 (61.5 mg, 0.19 mmol, 1.5 eq). The resulting mixture was stirred for 30 min at room temperature then ethyl bromoacetate (25.2 mg, 0.15 mmol, 1.2 eq) was ... | CCOC(=O)COc1ccc(F)c(NCc2cc(-c3cccc(F)c3)cc(C)c2OC)c1F | null | 107.1 | null |
501,217 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [S:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13](O)=[O:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>CCOCC>[S:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[CH2:13][OH:14])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3] | Cc1ccc(S(=O)(=O)N2CCC[C@H]2C(=O)O)cc1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCOCC | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-tosyl-L-proline (17.8 g) prepared in Reference Example 38 in anhydrous ether (80 ml) was dropwise added to a suspension of lithium aluminum hydride (3.76 g) in anhydrous ether (80 ml) over 30 minutes with ice-cooling. After stirring the reaction liquid at room temperature for one hour, 100 ml of ethyl a... | Cc1ccc(S(=O)(=O)N2CCC[C@H]2CO)cc1 | null | 53.1 | null |
1,700,428 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH2:23]([NH:25][CH2:26][CH2:27][OH:28])[CH3:24]>>[Br:1][C:2]1[C:3]([N:25]([CH2:23][CH3:24])[CH2:26][CH2:27][OH:28])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:... | CCNCCO | O=C(Nc1ccc(OC(F)(F)Cl)cc1)c1cnc(Cl)c(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in an analogous fashion to that described in Stage 33.1 using 5-bromo-6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)nicotinamide (Stage 169.2) and 2-ethylamino-ethanol to afford an off-white crystalline solid. (Reaction Time was 10 h). HPLC (Condition 4) tR=6.1 min, UPLC-MS (Condition 3) t... | CCN(CCO)c1ncc(C(=O)Nc2ccc(OC(F)(F)Cl)cc2)cc1Br | null | null | null |
685,537 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[NH2:19])([CH3:4])([CH3:3])[CH3:2].C([O:25][C:26](=O)[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]2[CH:41]=[C:40]([CH3:42])[N:39]=[C:38]([CH:43]3[CH2:45][CH2:44]3)[CH:37]=2)[CH:31]=1)=[O:29])(C)(... | Cc1cc(NC(=O)OC(C)(C)C)c(N)cc1C(F)(F)F | Cc1cc(-c2cccc(C(=O)CC(=O)OC(C)(C)C)c2)cc(C2CC2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (2-amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J20) (218 mg, 0.75 mmol) and 3-[3-(2-cyclopropyl-6-methyl-pyridin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester (Example K36) (264 mg, 0.75 mmol) according to the general procedure M. Obtained ... | Cc1cc(-c2cccc(C(=O)CC(=O)Nc3cc(C(F)(F)F)c(C)cc3NC(=O)OC(C)(C)C)c2)cc(C2CC2)n1 | null | null | null |
776,005 | ord_dataset-bf316bf78f4f45d4b275959c08104b7c | null | 2007-01-01T00:06:00 | true | [F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].[CH3:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.[OH-].[Na+]>>[CH3:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30... | CN1CCC(c2c[nH]c3ccc(O)cc23)CC1 | O=S(=O)(Cl)c1ccc(F)c(F)c1F | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By a method similar to Example 31, using 2,3,4-trifluorobenzenesulfonyl chloride (280 mg, 1.2 mmol) and 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (231 mg, 1.0 mmol) and 0.2 N sodium hydroxide (5.5 mL, 1.1 mmol) gave 449 mg of a purple foam. The crude product was purified by radial chromatography (silica gel, 2000 ... | CN1CCC(c2c[nH]c3ccc(OS(=O)(=O)c4ccc(F)c(F)c4F)cc23)CC1 | null | 105.8 | null |
302,199 | ord_dataset-9ad0840101374618a7d5c4e4521c82d1 | null | 1994-01-01T00:12:00 | true | [CH2:1]([C@H:7]1[C@H:10]([CH2:11][C@H:12]([OH:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]([NH2:54])(=[O:53])[C:46]1[C:47](=[CH:49][CH:50]=[CH:51][CH:52]=1)O.N(C(OC(C)(C)C... | CCCCCCCCCCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCC | NC(=O)c1ccccc1O | null | CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | null | 1.1 g of (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone, 1.6 g of triphenylphosphine, 0.825 g of salicylamide and 3 g of molecular sieve (4Å) were treated with 20 ml of THF and cooled to 0° C. Thereupon, 1.4 g of di-t-butyl azodicarboxylate were added. After warming to room temperature and stirring the reaction ... | CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)Oc1ccccc1C(N)=O | null | 49.5 | null |
1,112,668 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[C:15]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25])[CH:16]=1)[CH3:2].[C:29](Cl)(=[O:31])[CH3:30]>>[C:29]([CH2:2][CH2:1][NH:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:13])([F:14])[F:12])[CH... | CC(=O)Cl | CCNCc1cc(C(F)(F)F)ccc1-c1cc(C(F)(F)C(=O)O)ccc1OC | null | null | null | null | null | null | null | 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 6, using the following starting materials: (2′-ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-difluoro-acetic acid and acetyl chloride. | COc1ccc(C(F)(F)C(=O)O)cc1-c1ccc(C(F)(F)F)cc1CNCCC(C)=O | null | null | null |
123,911 | ord_dataset-d6752864fa634eb3b05f7440b4fb9a70 | null | 1984-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][C:8]2[C:13]([OH:14])=[CH:12][C:11]3[O:15][CH2:16][O:17][C:10]=3[CH:9]=2)=[CH:5][CH:4]=1.[CH:20]1C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[C:13]([O:14][CH3:20])=[CH:12][C:11]3[O:15][CH2:16][O:17][C:10]=3[CH:9]=2)=[CH:18][CH:19]=1 | COc1ccc(Cc2cc3c(cc2O)OCO3)cc1 | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (4-Methoxybenzyl)-3,4-methylenedioxy-6-methoxybenzene was prepared from 6-(4-methoxybenzyl)-3,4-methylenedioxyphenol (L. Jurd, Tetrahedron, Vol. 33, pp. 163-168 (1977)) by methylation as described above in H. Colorless prisms were obtained from benzene-solve F, m.p. 56°-57° (Found: C, 70.5; H, 5.95. Calc. for C16H16O4 ... | COc1ccc(Cc2cc3c(cc2OC)OCO3)cc1 | null | null | null |
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