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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
313,781 | ord_dataset-bd998d3fe946475e835418aaf647c00d | null | 1995-01-01T00:08:00 | true | [Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(=S)=S>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:5](=[O:8])[CH2:6][CH3:7])=[CH:13][CH:12]=1 | CCC(=O)Cl | Brc1ccccc1 | null | Cl | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | S=C=S | null | null | null | null | null | null | null | null | null | null | 0 | null | 294 g of aluminium chloride was added to 1000 ml of carbon disulfide and stirred. The reaction solution was cooled to 0° C. or lower, and 166 g of propionyl chloride was dropwise added thereto. Next, 283 g of bromobenzene was dropwise added thereto. Then, the whole was stirred for one hour at room temperature. After re... | CCC(=O)c1ccc(Br)cc1 | null | 78.7 | null |
1,141,619 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH2:1]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:13][Li]>C(OCC)C>[CH2:1]([C:5]1[S:9][C:8]([C:10](=[O:12])[CH3:13])=[CH:7][CH:6]=1)[CH:2]([CH3:3])[CH3:4] | [Li]C | CC(C)Cc1ccc(C(=O)O)s1 | 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 | 25 | 1 | To a solution of 5-isobutyl-thiophene-2-carboxylic acid (550 mg, 2.99 mmol) in diethyl ether (20 mL), a solution of methyl lithium (3.75 mL, 1.6 M in diethyl ether) is slowly added at rt. The reaction mixture is stirred at rt for 1 h before it is carefully washed twice with water, dried over MgSO4, filtered and evapora... | CC(=O)c1ccc(CC(C)C)s1 | null | null | null |
1,349,745 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[F:11].Cl.[CH3:14][NH:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([N:15]([CH3:16])[CH3:14])=[CH:6][C:5]=1[F:11] | COC(=O)c1ccc(F)cc1F | CNC | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 55 | 5 | To a stirred solution of 3.87 g (22.5 mmol) 2.4-difluoro-benzoic acid methyl ester (Apollo) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 5 h at 55° C. in an autoclave and was reduced with high vac... | COC(=O)c1ccc(N(C)C)cc1F | null | 55 | null |
1,642,909 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | O.[NH2:2][NH2:3].F[C:5]1[C:10]([F:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1.O>C(O)C>[F:11][C:10]1[C:5]([NH:2][NH2:3])=[N:6][CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=1 | Fc1cc(C(F)(F)F)cnc1F | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of hydrazine hydrate (100%) (3.45 ml) in ethanol (150 ml) was added dropwise a solution of 2,3-difluoro-5-(trifluoromethyl)pyridine (4.45 g) in ethanol (50 ml) at room temperature, stirred at the same temperature for 2 hours, and then additionally stirred at 80° C. for 2 hours. Then, the mixture was allow... | NNc1ncc(C(F)(F)F)cc1F | null | null | null |
223,723 | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | null | 1991-01-01T00:02:00 | true | [H-].[Na+].[C:3]1([C:9]2[O:10][CH:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]([OH:15])[CH2:13][N:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]=[C:30]=[O:31]>>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30]([O:15][CH:12]1[CH:11]([C:16]2... | O=C=Nc1ccccc1F | OC1CN=C(c2ccccc2)OC1c1ccccc1 | 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 | Working in a manner similar to that described in Example 16, but starting with an oily suspension (50% by weight; 0.31 g) of sodium hydride, (5RS, 6SR)-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1.52 g) and 2-fluorophenyl isocyanate (0.9 g), and after recrystallization in diisopropyl ether, (5RS, 6SR)-5-(2-fluorophen... | O=C(Nc1ccccc1F)OC1CN=C(c2ccccc2)OC1c1ccccc1 | null | 28.6 | null |
1,579,016 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:21]([C:23]3[O:24][C:25]4[C:30]([C:31](=[O:40])[C:32]=3[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:22])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)C)=[CH:13][CH:12]=3)[C:3]=12.Cl.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>C(O... | CC(=O)Nc1ccc(-c2nn(C(C)c3oc4ccccc4c(=O)c3-c3cccc(F)c3)c3ncnc(N)c23)cc1 | null | null | Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCO | null | null | null | null | null | null | null | null | null | null | null | To a solution of Example 107 (0.080 g, 0.149 mmoles) in ethanol (5 ml), Con.HCl (0.5 ml) was added and refluxed for 2 h. The reaction mixture was basified with sodium carbonate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude ... | CC(c1oc2ccccc2c(=O)c1-c1cccc(F)c1)n1nc(-c2ccc(N)cc2)c2c(N)ncnc21 | null | 27.3 | null |
764,382 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)=[O:13].CCCCCC>CN(C)C=O>[CH2:1]([NH:8][CH2:10][CH2:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)=[O:13])[C:2]1[CH:7]=[C... | O=C(CCCl)Nc1ccc2[nH]ncc2c1 | NCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 80 | 1 | N-benzylamine (4.0 ml, 36.5 mmol) was added to a solution of 3-chloro-N-(1H-indazol-5-yl)propanamide (1.70 g, 7.60 mmol) in N,N-dimethylformamide (2 ml), and the resulting mixture was stirred at 80° C. for 1 hour. Then, the reaction solution was cooled to 0° C. and hexane was added thereto to effect suspension. The sol... | O=C(CCNCc1ccccc1)Nc1ccc2[nH]ncc2c1 | null | 44.7 | null |
1,647,183 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [Br:1][C:2]([CH3:7])([CH3:6])[C:3](Br)=[O:4].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOC(C)=O>[Br:1][C:2]([CH3:7])([CH3:6])[C:3]([NH:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4] | CC(C)(Br)C(=O)Br | NCc1ccccc1 | 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 | Prepared in 91% yield (10.7 g, 42 mmol) from the reaction of 2-bromo-2-methylpropanoyl bromide (10.6 g, 46 mmol) with benzylamine (5.1 mL, 46 mmol) via general procedure A. Rf=0.84 (3:1, hexanes:EtOAc); mp 73.4-75.5° C.; 1H NMR (400 MHz, CDCl3): δ 7.41-7.23 (m, 1H), 7.03 (br s, 1H), 4.46 (d, J=5.8 Hz, 1H), and 1.99 (s,... | CC(C)(Br)C(=O)NCc1ccccc1 | null | 91 | null |
1,042,584 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]([N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][C:30]=3[N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[C:25]2=[O:40])[CH2:12][CH2:13][CH2:14][NH:15][S:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)(=[O:18])=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClC(Cl)C.C(N(CC)CC)C.[C... | COc1ccc([C@@H](CCCNS(=O)(=O)c2cccs2)N2C(=O)c3cccc(N4CCNCC4)c3C2=O)cc1OC | O=C1CCCC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 3 | A 50-mL round bottom flask was charged with Compound 167 (10.0 mg, 0.016 mmol) and dichloroethane (2.3 mL). Triethylamine (2.5 μL, 0.018 mmol) was added followed by cyclopentanone (7.1 μL, 0.06 mmol) and sodium triacetoxyborohydride (4.7 mg, 0.022 mmol). The mixture was stirred at room temperature for 3 h. The mixture ... | COc1ccc([C@@H](CCCNS(=O)(=O)c2cccs2)N2C(=O)c3cccc(N4CCN(C5CCCC5)CC4)c3C2=O)cc1OC | null | 48.8 | null |
1,032,881 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[C@@H:4]([CH:15]([CH3:17])[CH3:16])[CH2:3]1.C(Cl)[Cl:19]>CO.Cl.O1CCOCC1>[ClH:19].[ClH:19].[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C@@H:4]([CH:15]([CH3:17])[CH3:16])[CH2:3]1 | CC(C)[C@H]1CN(C)CCN1C(=O)OC(C)(C)C | ClCCl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | 25 | 8 | 1,1-Dimethylethyl (2S)-4-methyl-2-(1-methylethyl)-1-piperazinecarboxylate (2.18 g crude, 8.76 assumed mmol) was dissolved in a mixture of MeOH (5 mL), CH2Cl2 (5 mL), and 4 N HCl in dioxane (8 mL). After stirring overnight at room temperature, another 8 mL of 4 N HCl in dioxane and 8 mL of MeOH were added, which dissolv... | CC(C)[C@H]1CN(C)CCN1 | null | null | null |
360,416 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[C:29]([O:31][CH3:32])=[O:30])[NH2:25]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:25][C:24]3[C... | O=C(O)CC1CCc2cc(Br)cc3[nH]c(=O)c(=O)n1c23 | COC(=O)c1ccc(N)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (340 mg, 1 mmol) and m-chloro-p-methoxycarbonylaniline (200 mg, 1.08 mmol) to give 230 mg of the title compound (45%): mp 167° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12... | COC(=O)c1ccc(NC(=O)CC2CCc3cc(Br)cc4[nH]c(=O)c(=O)n2c34)cc1Cl | null | 45.4 | null |
393,087 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | O[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH:14]=[CH:15][C:16]1[CH:20]=[CH:19][S:18][CH:17]=1.[N:21]1C(C)=CC=C[C:22]=1C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.CN>C(Cl)Cl>[CH3:22][NH:21][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH:14]=... | Cc1cccc(C)n1 | OCCCn1c(C=Cc2ccsc2)cc2ccccc21 | null | CN | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 3 | A solution of 1-(3-hydroxypropyl)-2-[2-(thiophen-3-yl)vinyl]indole (121 mg) in 3 ml of methylene chloride was treated with 120 μl of 2,6-lutidine and cooled to 0° C. Trifluoromethanesulfonic anhydride (100 μl) was added, and after stirring for 30 minutes 5 ml of 40% aqueous methylamine was introduced, and the reaction ... | CNCCCn1c(C=Cc2ccsc2)cc2ccccc21 | null | 67 | null |
81,003 | ord_dataset-f196f0a87dd74fcd82ca019f8ff5cf9c | null | 1981-01-01T00:05:00 | true | [C:1]([CH2:3][CH:4]=[CH:5][C:6]1[C:7]([NH2:22])=[N:8][C:9](=[O:21])[N:10]([CH:20]=1)[C@@H:11]1[O:19][C@H:16]([CH2:17][OH:18])[C@@H:14]([OH:15])[C@H:12]1[OH:13])#[N:2]>[Pd].CO>[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[C:7]([NH2:22])=[N:8][C:9](=[O:21])[N:10]([CH:20]=1)[C@@H:11]1[O:19][C@H:16]([CH2:17][OH:18])[C@@H:14]([OH:15])[... | N#CCC=Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)nc1N | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 5-(3-cyanopropen-1-yl)cytidine (0.73 mmol) and 20 ml methanol in a 250 ml hydrogenation flask is added 25 mg of 10% Pd/C. The system is evacuated, repressurized with two atmospheres hydrogen gas and then stirred at room temperature. After about two hours, the system is evacuated and the resulting black... | N#CCCCc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)nc1N | null | null | null |
573,364 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[CH:15][N:16]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].O.NN>CCO>[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][NH2:16])([CH3:2])([CH3:4])[CH3:3] | CC(C)(C)OC(=O)Cc1ccccc1C=CN1C(=O)c2ccccc2C1=O | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A solution of {2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-vinyl]-phenyl}-acetic Acid tert-butyl ester (1.97 g) and hydrazine hydrate (1.97 mL) in EtOH (75 mL) was heated at reflux for 90 minutes. The solids were removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (50 mL)... | CC(C)(C)OC(=O)Cc1ccccc1CCN | null | 66.9 | null |
1,752,600 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[F:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[C@:24]12[CH2:33][O:32][C@@H:31]([CH:34]([OH:39])[CH2:35][CH2:36][CH2:37]O)[CH2:30][C@H:29]1[CH2:28][S:27][C:26]([NH:40][C:41](=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[N:25]2.CC1C=CC=C(C)N=1>ClCCl>[F:16][C:17]1... | O=C(NC1=N[C@@]2(c3ccc(F)cc3F)CO[C@@H](C(O)CCCO)C[C@H]2CS1)c1ccccc1 | null | null | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1cccc(C)n1 | ClCCl | null | null | null | null | null | null | null | null | null | 0 | null | Trifluoromethanesulfonic anhydride (12.5 μL, 76 μmol) was added drop-wise to a −78° C. solution of N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(1,4-dihydroxybutyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (C12) (18 mg, 38 μmol) and 2,6-dimethylpyridine (17.6 μL, 152 μmol) in dichloromethane (0.65 m... | O=C(NC1=N[C@@]2(c3ccc(F)cc3F)CO[C@@H](C3CCCO3)C[C@H]2CS1)c1ccccc1 | null | null | null |
716,600 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[NH:9]1[C:17]2[C:12](=[C:13]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:26]=[C:27]([NH:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:28]=[CH:29][CH:30]=4)[CH2:21][CH2:20]3)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:9]2[C:17]3[C:12... | CC(C)C(=O)Nc1cccc(C2CCN(Cc3cccc4[nH]ccc34)CC2)c1 | Fc1ccc(I)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 | Prepared by Procedure C and Scheme Q1, with CuBr in place of Cu, using 1-fluoro-4-iodobenzene and N-{3-[1-(1H-indol-4-ylmethyl)-4-piperidinyl]phenyl}-2-methylpropanamide: 1H NMR (400 MHz, CDCl3) δ 7.66–6.92 (m, 12H), 6.65 (d, 1H, J=3.2 Hz), 3.69 (s, 2H), 3.15–3.02 (m, 2H), 2.58–2.40 (m, 2H), 2.20–2.04 (m, 2H), 1.94–1.7... | CC(C)C(=O)Nc1cccc(C2CCN(Cc3cccc4c3ccn4-c3ccc(F)cc3)CC2)c1 | null | null | null |
1,432,863 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [F:1][C:2]([F:33])([F:32])[C@H:3]([NH:5][S:6]([C:9]1[CH:10]=[N:11][C:12]([C:15]2[N:16]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:17]3[C:22]([C:23]=2[C:24]#[N:25])=[CH:21][CH:20]=[C:19]([CH3:26])[CH:18]=3)=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH3:4].[Br:34]Br>O>[F:33][C:2]([F:1])([F:32])[C@H:3]([NH:5][S:6]([C:9]1[CH:10]=... | Cc1ccc2c(C#N)c(-c3ccc(S(=O)(=O)N[C@H](C)C(F)(F)F)cn3)n(C3CCCC3)c2c1 | BrBr | 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 | 90 | 0.5 | To a solution of (R)-6-(3-cyano-1-cyclopentyl-6-methyl-1H-indol-2-yl)-pyridine-3-sulfonic acid (2,2,2-trifluoro-1-methyl-ethyl)-amide (0.48 g, 1.05 mmol) in acidic acid (3 mL) was added bromine (0.35 g, 2.1 mmol) dropwise. The solution was stirred at 90° C. for 30 min, cooled to room temperature and then diluted with w... | Cc1cc2c(cc1Br)c(C#N)c(-c1ccc(S(=O)(=O)N[C@H](C)C(F)(F)F)cn1)n2C1CCCC1 | null | 92.6 | null |
70,575 | ord_dataset-06d4002fc4d34860a0688cba690e12dc | null | 1980-01-01T00:09:00 | true | [NH2:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][CH:3]=1.[NH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([N+:30]([O-])=O)=[CH:22][CH:21]=1>>[CH3:3][C:2]1([CH3:15])[NH:30][C:23]2[C:24]3[C:29]([C:20]([N:19]=[N:1][C:2]4[C:15]... | Nc1ccc([N+](=O)[O-])c2ccccc12 | Nc1ccc([N+](=O)[O-])c2cc3ccccc3cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In the manner described in Example 8, substituting 12.0 grams of 1-amino-4-nitroanthracene for the 1-amino-4-nitronaphthalene, the desired compound is obtained. | CC1(C)Nc2cccc3c(N=Nc4ccc([N+](=O)[O-])c5cc6ccccc6cc45)ccc(c23)N1 | null | null | null |
858,058 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | C([O:4][CH2:5][C:6]1[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH2:26]C)=[O:24])[C:17]([O:19][CH2:20]C)=[O:18])=[CH:13][C:12]([Br:28])=[C:11]2[C:7]=1[C:8]([Cl:29])=[N:9][NH:10]2)(=O)C.CO.C[O-].[Mg+2].C[O-]>>[Br:28][C:12]1[CH:13]=[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:17]([O:19][CH3:20])=[... | CCOC(=O)C[C@H](Cc1cc(Br)c2[nH]nc(Cl)c2c1COC(C)=O)C(=O)OCC | null | null | C[O-] | [Mg+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 18 | (S)-Diethyl 2-((4-(acetoxymethyl)-7-bromo-3-chloro-1H-indazol-5-yl)methyl)succinate (550 mg, 1.123 mmol) was dissolved in methanol (15 mL, 370 mmol). 6-10% Magnesium methoxide in methanol (3.4 mL, 2.57 mmol) was added to the mixture. Reaction stirred at room temperature for 18 hours. Reaction was quenched with 6 mL of ... | COC(=O)C[C@H](Cc1cc(Br)c2[nH]nc(Cl)c2c1CO)C(=O)OC | null | 96 | null |
270,425 | ord_dataset-a20aed058d7b40bc81fdf50bc5b03f97 | null | 1993-01-01T00:06:00 | true | [C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:19]([O:21][C:22](=[O:30])[CH2:23][NH:24][CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[CH3:20].C(OCC)(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.Cl>[CH2:19]([O:21][C:22](=[O:30])[CH2:23][N:24]([C:16](=[O:... | CCOC(=O)CNC1CCCC1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O | null | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | null | CBZ-L-Valine (15.1 g, 0.06 mol) was dissolved in CH2Cl2 (250 mL) and the following reagents were added in equal molar amounts in the stated order; 4-Dimethylaminopyridine (DMAP), ethyl-N-(cyclopentyl)glycinate and WSCDI. The reaction mixture was allowed to stir at room temperature over night. Evaporation of the solvent... | CCOC(=O)CN(C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C1CCCC1 | null | null | null |
39,528 | ord_dataset-de10a15943a54ac7a3c3e1c774d21392 | null | 1978-01-01T00:04:00 | true | [P:1]([OH:5])([O-:4])([O-:3])=[O:2].[Ca+2:6].[S:7]([O-:11])([O-:10])(=[O:9])=[O:8].[K+:12].[K+]>>[OH:3][P:1]([O-:5])([OH:4])=[O:2].[K+:12].[S:7]([O-:11])([O-:10])(=[O:9])=[O:8].[Ca+2:6] | O=P([O-])([O-])O | null | null | O=S(=O)([O-])[O-] | [Ca+2] | [K+] | null | null | null | 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 monocalcium phosphate solid was then reacted with a stoichiometric amount of potassium sulfate in aqueous solution to form KH2PO4 and calcium sulfate. The calcium sulfate precipitate is separated by filtration and recovered. The solution or filtrate from this filtration is subjected to evaporation for the precipita... | O=P([O-])(O)O | null | null | null |
1,289,338 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | O[C@H:2]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[CH2:3][CH2:4][C:5]([O:7]C)=[O:6]>C(Cl)Cl.FC(F)(F)C(O)=O>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C@H:2]2[O:7][C:5](=[O:6])[CH2:4][CH2:3]2)[CH:14]=[CH:13][CH:12]=1 | COC(=O)CC[C@H](O)c1cccc(OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 8 | The (S)-methyl 4-hydroxy-4-(3-methoxyphenyl)butanoate (985 mg) is dissolved in CH2Cl2 (10 mL), and the solution is cooled to 0° C. Trifluoroacetic acid (˜4 drops) is added and the mixture is stirred for 8 h at room temperature to complete the lactonization. The reaction is quenched with aqueous sodium bicarbonate, and ... | COc1cccc([C@@H]2CCC(=O)O2)c1 | null | 98 | null |
1,021,680 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH3:19])=[CH:14][C:13]=1[C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:22][CH:21]=1>ClCCl.C(N(CC)CC)C>[CH2:1]([NH:8][C:9](=[O:10])[N:18]([C:15]1[CH:16]=[CH:17][C:1... | CCCCCCCN=C=O | CCOC(=O)/C=C/c1ccc(-c2cc(NC)ccc2C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 50 | 12 | 660 μL (4.0 mmol, 1.5 eq) of heptyl isocyanate are added to a solution of 805 mg (2.72 mmol, 1 eq) of ethyl (E)-3-(2′-methyl-5′-methylaminobiphenyl-4-yl)acrylate in 8 mL of a 7/1 dichloromethane/triethylamine mixture. The reaction medium is stirred at 50° C. for 12 hours and then hydrolyzed with water and extracted wit... | CCCCCCCNC(=O)N(C)c1ccc(C)c(-c2ccc(/C=C/C(=O)OCC)cc2)c1 | null | 77.5 | null |
963,917 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[C:28](=[O:40])[N:29]([C:33]6[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=6)[N:30]=[CH:31][CH:32]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10]([C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)=[N:9]2)=CC=1.C(O)(... | COc1ccc(Cn2nc(-c3cnn(C)c3)c3c(Oc4ccc(NC(=O)c5ccnn(-c6ccc(F)cc6)c5=O)cc4F)ccnc32)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 60 | null | A 50 mL round-bottomed flask was charged N-(4-(1-(4-methoxybenzyl)-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (23.8 mg, 0.0360 mmol) and CF3COOH (5 mL). The reaction mixture was stirred at 60° C. until LC-MS showed that th... | Cn1cc(-c2n[nH]c3nccc(Oc4ccc(NC(=O)c5ccnn(-c6ccc(F)cc6)c5=O)cc4F)c23)cn1 | null | 58.1 | null |
748,421 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)[S:18][CH2:19][C:20](O)=[O:21].[O-]S([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1]... | Nc1ccc(C(=O)c2ccc(Cl)cc2)cc1C(SCC(=O)O)c1cccc(Cl)c1 | null | null | O=S(=O)([O-])[O-] | [Mg+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of intermediate (19) (0.079 mol) and MgSO4 (35.5 g) in toluene (500 ml) was stirred and refluxed overnight in a Dean-Stark apparatus and then cooled. The precipitate was filtered off and the filtrate was evaporated till dryness. The residue (35 g) was purified by column chromatography over silica gel (eluent:... | O=C1CSC(c2cccc(Cl)c2)c2cc(C(=O)c3ccc(Cl)cc3)ccc2N1 | null | 4.4 | null |
1,578,151 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH3:1][NH:2][CH3:3].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]([N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:29](O)=[O:30])[CH:27]=3)[CH2:22][CH2:21]2)=[O:19])[CH2:13][C@H:12]1[CH3:32])=[O:10])([CH3:7])([CH3:6])[CH3:5]>>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]([N:20]2[C:28]3[C:... | C[C@@H]1CN(CC(=O)N2CCc3ccc(C(=O)O)cc32)CCN1C(=O)OC(C)(C)C | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting with dimethylamine and 1-[2-((R)-4-tert-butoxycarbonyl-3-methyl-piperazin-1-yl)-acetyl]-2,3-dihydro-1H-indole-6-carboxylic acid, the title compound was prepared by using similar methods to those described in General Procedure 1. MS: [M+H]+=431. | C[C@@H]1CN(CC(=O)N2CCc3ccc(C(=O)N(C)C)cc32)CCN1C(=O)OC(C)(C)C | null | null | null |
935,695 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [CH3:1][CH:2]([CH3:19])[CH2:3][C@H:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]([O:7]CCCCC)=[O:6].O.[OH-].[Li+]>C1COCC1.O.Cl>[CH3:1][CH:2]([CH3:19])[CH2:3][C@H:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]([OH:7])=[O:6] | CCCCCOC(=O)[C@H](CC(C)C)OCCCCC | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of (2S)-pentyl 4-methyl-2-pentyloxypentanoate 9 (80 mg, 0.3 mmol) in 20 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (25 mg, 0.6 mmol) in 5 mL of water. The reaction mixture was stirred at rt for 16 h. THF was removed under reduced pressure to give an yellow oil... | CCCCCO[C@@H](CC(C)C)C(=O)O | null | 74.2 | null |
1,476,732 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1.[Br:17][C:18]1[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([I:25])[N:19]=1.O>CN(C)C=O>[Br:17][C:18]1[C:23]([O:24][CH2:13][C:12]2[CH:15]=[CH:16][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[CH:22][CH:21]=[C:20]([I:25])[N:19]=1 | COc1ccc(CCl)cc1 | Oc1ccc(I)nc1Br | 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 | 25 | 6 | Potassium carbonate (12 g) and 4-methoxybenzyl chloride (8.8 mL) were added to a solution of 2-bromo-6-iodopyridin-3-ol (12 g) in N,N-dimethylformamide (130 mL), and the mixture was stirred at room temperature for six hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The org... | COc1ccc(COc2ccc(I)nc2Br)cc1 | null | 100 | null |
1,186,214 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][O:14][C:15]2[C:25]3[O:24][CH2:23][CH2:22][NH:21][C:20](=O)[C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:7]1([CH2:13][O:14][C:15]2[C:25]3[O:24][CH2:23][CH2:22][NH:21][CH2:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9]... | O=C1NCCOc2c(OCc3ccccc3)cccc21 | 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 | 60 | null | 1M Lithium aluminum hydride (60 ml, 60.0 mmol) in THF was added to a stirred solution of 9-[(phenylmethyl)oxy]-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (Preparation 59) (7.4 g, 27.5 mmol) in THF (150 ml) under argon and heated at 60° C. for 2 hours then cooled and quenched by careful addition of 100 ml of 2M sodium hydro... | c1ccc(COc2cccc3c2OCCNC3)cc1 | null | 99.8 | null |
1,442,412 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.S(Cl)(Cl)=O.[CH3:17]O>>[CH3:17][O:11][C:10]([C:8]1[CH:7]=[CH:6][C:5]2[S:1][CH:2]=[N:3][C:4]=2[CH:9]=1)=[O:12] | CO | O=C(O)c1ccc2scnc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 60 | 15 | To a suspension of benzothiazole-5-carboxylic acid (1 eq.) in MeOH at 0° C. was added dropwise thionyl chloride (2 eq.). The reaction was stirred at 60° C. for 15 h. The solvents were concentrated under reduced pressure to afford benzothiazole-5-carboxylic acid methyl ester. | COC(=O)c1ccc2scnc2c1 | null | null | null |
625,938 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [CH2:1]1COCC1.[CH3:6][C:7]1[C:11]([CH:12]=[O:13])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:9][N:8]=1.C[Mg]Br.Cl>C(OCC)(=O)C>[CH3:6][C:7]1[C:11]([CH:12]([OH:13])[CH3:1])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:9][N:8]=1 | C1CCOC1 | Cc1noc(-c2ccccc2)c1C=O | null | C[Mg]Br | Cl | 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 | 25 | 1 | To the THF solution of the above Compound 25 was slowly added 1.4 eq of methylmagnesium bromide at room temperature. The reaction mixture was stirred at r.t. for 1 h. To the reaction mixture was added ethyl acetate and 1N HCl. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was rem... | Cc1noc(-c2ccccc2)c1C(C)O | null | 96 | null |
850,348 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | ClC1N2[C:8](=[O:11])NN=C2C(C2C=CC(Cl)=CC=2)=C(C2C=CC(Cl)=CC=2)N=1.[Cl-].ICC.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:42]=[C:41]([N:43]3[CH2:46][C:45](NCC)(C(N)=O)[CH2:44]3)[N:40]3[C:53](=[O:58])[N:54]([CH2:56][CH3:57])[N:55]=[C:39]3[C:38]=2[C:59]2[CH:64]=[CH:63][C:62]([Cl:65])=[CH:61][CH:60]=2)=[CH:33][CH:32]=1>>[... | O=c1[nH]nc2c(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3)nc(Cl)n12 | CCNC1(C(N)=O)CN(c2nc(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3)c3nn(CC)c(=O)n23)C1 | null | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCI | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in two steps from 5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one by nucleophilic displacement of chloride with the requisite amine, followed by alkylation with iodoethane, in a manner analogous to that in which 1-(7,8-bis(4-chlorophenyl)-2-ethyl-3-oxo-2,3-dihy... | CCn1nc2c(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3)nc(N3CCOCC3)n2c1=O | null | null | null |
1,232,801 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [F:1][C:2]1[CH:22]=[N:21][CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[C:10]([Cl:17])=[CH:9][C:8]=1[OH:18])=O.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Cl:17][C:10]1[C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]2[N:6]=[C:4]([C:3]3[CH:1... | O=C(Nc1cc(C(F)(F)F)c(Cl)cc1O)c1ccncc1F | null | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 1 | To a mixture of 2.08 g of 3-fluoro-N-[4-chloro-2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 13 ml of tetrahydrofuran and 1.79 g of triphenylphosphine, 2.98 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for one hour. The reaction mi... | Fc1cnccc1-c1nc2cc(C(F)(F)F)c(Cl)cc2o1 | null | 88.4 | null |
852,037 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | C(Cl)(=O)C(Cl)=O.[CH3:7][NH:8][C:9](=O)[CH3:10].N1C(C)=CC=CC=1C.[C:20]([NH:28][NH2:29])(=O)[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:7][N:8]1[C:9]([CH3:10])=[N:29][N:28]=[C:20]1[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1 | CNC(C)=O | NNC(=O)c1ccncc1 | null | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | Cc1cccc(C)n1 | null | null | null | null | null | null | null | null | null | 25 | 1 | 860 μl (10 mmol) oxalyl chloride was slowly added to a solution of 731 mg (10 mmol) N-methyl-acetamide and 2.33 ml (20 mmol) 2,6-lutidine in 20 ml CH2Cl2 at 0° C. After 15 min 1.37 g (10 mmol) isonicotinic acid hydrazide was added in one portion. The resulting mixture was stirred at room temperature for 1 h and the neu... | Cc1nnc(-c2ccncc2)n1C | null | 43.9 | null |
1,224,807 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [CH2:1]([C:3]1[O:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:6][C:7]=1[CH:8]=[O:9])[CH3:2].[CH2:20]([Mg]Br)[CH:21]([CH3:23])[CH3:22].O1CCCC1>>[CH2:1]([C:3]1[O:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][CH:11]=2)=[CH:6][C:7]=1[CH:8]([OH:9])[CH2... | CCc1oc(-c2ccc(C(F)(F)F)cc2)cc1C=O | CC(C)C[Mg]Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | An operation similar to that in Example 3 (2) was performed using 2-ethyl-5-[4-(trifluoromethyl)phenyl]-3-furaldehyde (805 mg) and 1N isobutylmagnesium bromide-tetrahydrofuran solution (6.0 mL) to give the title compound (819 mg, 83%) as an oil. | CCc1oc(-c2ccc(C(F)(F)F)cc2)cc1C(O)CC(C)C | null | 83 | null |
645,981 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | C([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2([C:13]([F:16])([F:15])[F:14])[N:12]=[N:11]2)[CH:5]=1)=O.Cl.[OH-].[Na+]>CO>[F:16][C:13]([F:14])([F:15])[C:10]1([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[NH2:3])[N:11]=[N:12]1 | O=CNc1cccc(C2(C(F)(F)F)N=N2)c1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | null | N-formyl m-[3-(trifluoromethyl)diazirine-3-yl]aniline (120 mg) is dissolved in 3 ml of methanol. Concentrated HCl (1 ml) is added. The mixture is reacted for 10 min at ambient temperature. The reaction mixture is cooled to 0° C. in an ice bath and neutralised with NaOH (3 ml, 6N). The aqueous phase is extracted with et... | Nc1cccc(C2(C(F)(F)F)N=N2)c1 | null | null | null |
1,320,520 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]#[N:12])=[C:9]([O:13][C:14]3[CH:15]=[C:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:17]=[CH:18][CH:19]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1>N1C=CC=CC=1>[C:11]([C:10]1[C:4]2[S:3][C:2]([NH:1][C:30]([CH:27]3[CH2:29][CH2:28]3)=[O:31])=... | O=C(Cl)C1CC1 | N#Cc1c(Oc2cccc(NC(=O)C(F)(F)F)c2)ccc2nc(N)sc12 | 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 | 2 | To a solution of N-{3-[(2-amino-7-cyano-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (1.5 g, 3.96 mmol) in pyridine (4 mL) was added cyclopropanecarbonyl chloride (467 μL, 5.15 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure. Th... | N#Cc1c(Oc2cccc(NC(=O)C(F)(F)F)c2)ccc2nc(NC(=O)C3CC3)sc12 | null | 71.3 | null |
1,207,742 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | B(F)(F)F.CSC.C[O:9][C:10]1[CH:11]=[C:12]([C:17]2[N:21]([CH2:22][C:23]#[N:24])[N:20]=[CH:19][C:18]=2[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([C:31]3[CH:36]=[CH:35][C:34]([C:37](=[O:39])[CH3:38])=[CH:33][CH:32]=3)[CH:26]=2)[CH:13]=[C:14]([CH3:16])[CH:15]=1>ClCCl>[OH:9][C:10]1[CH:11]=[C:12]([C:17]2[N:21]([CH2:22][C:23]#[N:24])... | COc1cc(C)cc(-c2c(-c3ccnc(-c4ccc(C(C)=O)cc4)c3)cnn2CC#N)c1 | null | null | FB(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CSC | null | null | null | null | null | null | null | null | null | null | 24 | Borontrifluoride-dimethylsulfide (0.25 mL, 2.37 mmol) was dropwise added to a solution of the methoxy compound (0.1 g, 0.24 mmol) prepared in Example 37 in dichloromethane (4 mL) at room temperature under nitrogen atmosphere, and stirred for 24 hours. The reaction mixture was concentrated by vacuum distillation. The re... | CC(=O)c1ccc(-c2cc(-c3cnn(CC#N)c3-c3cc(C)cc(O)c3)ccn2)cc1 | null | null | null |
732,748 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[N:10]([O-])=O.[Na+].[Sn](Cl)Cl>Cl.O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][NH2:10])[CH:6]=[CH:7][C:8]=1[F:9] | Nc1ccc(F)c(F)c1 | O=N[O-] | null | Cl | Cl[Sn]Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | -10 | 2 | A stirred mixture of 3,4-difluoroaniline (12.9 g, 0.1 mol) in concentrated hydrochloric acid (60 mL) was chilled to −10° C. with an ice/methanol bath. A solution of sodium nitrite (6.9 g, 0.1 mol) in water (30 mL) was added at a rate which maintained the temperature of the reaction mixture below 10° C. After stirring f... | NNc1ccc(F)c(F)c1 | null | 56.3 | null |
1,501,650 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:45]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38]([C@@H:40]1[CH2:44][CH2:43][NH:42][CH2:41]1)=[O:39].[C:46](Cl)(=[O:53])[C:... | O=C(Cl)c1ccccc1 | O=C(Nc1ccc2cc1CCc1cccc(c1)Nc1ncc(Cl)c(n1)N2)[C@@H]1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | The desired compound was prepared according to the procedure of Example A20, using (3R)—N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]pyrrolidine-3-carboxamide bis(trifluoroacetate) and benzoyl chloride as starting materials in 40% yield. LCMS for C3... | O=C(Nc1ccc2cc1CCc1cccc(c1)Nc1ncc(Cl)c(n1)N2)[C@@H]1CCN(C(=O)c2ccccc2)C1 | null | 40 | null |
408,868 | ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2 | null | 1998-01-01T00:08:00 | true | [NH2:1][C:2]1([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C(N(CC)CC)C>ClCl.O>[C:13]([NH:1][C:2]1([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1)(=[O:15])[CH3:14] | CC(=O)OC(C)=O | COc1ccc(C2(N)CC2)cc1 | null | ClCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | O | null | null | null | null | null | null | null | null | null | 25 | 22 | To a stirred suspension of Compound 7 (1.25 g, 7.66 mmol) in CH2 Cl2 (40 ml) was added acetic anhydride (860 mg, 8.42 mmol) and triethylamine (2.32 g, 22.98 mmol) at room temperature. The reaction mixture was stirred at room temperature for 22 h. The mixture was diluted with H2O (50 ml) and stirred for 10 min. The orga... | COc1ccc(C2(NC(C)=O)CC2)cc1 | null | 80.1 | null |
761,845 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [CH2:1]([O:3][C:4](=[O:32])[C@@H:5]([OH:31])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)[CH3:2].[CH2:33](I)[CH3:34]>ClCCl>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([O:31][CH2:33][CH3:34... | CCOC(=O)[C@@H](O)Cc1ccc(OCCCOc2ccc(Oc3ccccc3)cc2)cc1 | CCI | 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 (2S)-2-hydroxy-3-{4-[3-(4-phenoxy-phenoxy)-propoxy]-phenyl}-propionic acid ethyl ester, AgO2 (1.5 eq) and ethyl iodide (excess) in dichloromethane was stirred over 10 days. The crude mixture was filtered through celite and concentrated to dryness. The compound was purified by chromatography to give the ti... | CCOC(=O)C(Cc1ccc(OCCCOc2ccc(Oc3ccccc3)cc2)cc1)OCC | null | null | null |
304,408 | ord_dataset-180e296d6d6245638d4d22a59120ea01 | null | 1995-01-01T00:02:00 | true | Br[CH:2]([CH2:28][CH2:29][CH3:30])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:8]#[N:9].[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[CH2:39][NH:38][CH2:37][CH... | CCCC(Br)CCCCC(C#N)(Sc1ccc(C)cc1)c1ccc(OC)c(OC)c1 | COc1cc2c(cc1OC)CNCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The procedure of Example 3 is repeated using 0,836 g of α-(5-bromooctyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 0.675 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline. This affords 0,422 g of the desired product as a brown gum. | COc1ccc(C(C#N)(CCCCCCCCN2CCc3cc(OC)c(OC)cc3C2)Sc2ccc(C)cc2)cc1OC | null | 20,041 | null |
1,234,845 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [NH2:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([C:13]([C:15]2[C:16]([NH:25][CH2:26][C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)=[N:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[N:19][CH:20]=2)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][N:4]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:3]1.C(N(CC)CC)C.[C:46](OC(=O... | CC(=O)OC(C)=O | CC(C)CN(C(=O)c1cnc(C(C)(C)C)nc1NCc1ccco1)[C@H]1C[C@@H](N)CN(C(=O)OC(C)(C)C)C1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of tert-butyl (3R,5S)-3-amino-5-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-1-carboxylate (70 mg) in 1,2-dichloroethane (3 ml) were successively added triethylamine (55 μl) and acetic anhydride (35 μl), and the mixture was stirred at room temperature... | CC(=O)N[C@@H]1C[C@H](N(CC(C)C)C(=O)c2cnc(C(C)(C)C)nc2NCc2ccco2)CN(C(=O)OC(C)(C)C)C1 | null | null | null |
1,269,030 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:23]=[CH:22][C:21]4[C:17](=[CH:18][N:19]([CH2:24][C:25]([O:27]CC)=[O:26])[N:20]=4)[CH:16]=3)=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.[OH-].[Na+].O.Cl>C(O)C>[CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]2[N:11]=[CH:10][N:9... | CCCN(CC1CC1)c1cc(C(=O)Nc2ccc3nn(CC(=O)OCC)cc3c2)ncn1 | null | null | Cl | [Na+] | [OH-] | 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 | 25 | 2 | A solution of ethyl {5-[({6-[(cyclopropylmethyl)(propyl)amino]pyrimidin-4-yl}carbonyl)amino]-2H-indazol-2-yl}acetate (Example 120, 90 mg; 0.20 mmol) in ethanol (10 ml) was treated with 10% NaOH solution (5 ml). After stirring at RT for 2 hours the solvent was reduced in vacuo to one quarter of its original volume and w... | CCCN(CC1CC1)c1cc(C(=O)Nc2ccc3nn(CC(=O)O)cc3c2)ncn1 | null | null | null |
298,233 | ord_dataset-b6309a86b70f4ca08fd301828cacf950 | null | 1994-01-01T00:10:00 | true | Cl[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]1[N:23]=[CH:24][N:25]([CH3:28])[C:26]=1Cl)(=[O:21])=[O:20])(=[O:10])=[O:9]>[OH-].[Na+].[Pd]>[CH3:28][N:25]1[CH:26]=[C:22]([S:19]([NH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][S:8]([... | Cn1cnc(S(=O)(=O)NCCCCCCNS(=O)(=O)c2ncn(C)c2Cl)c1Cl | null | null | [Pd] | [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 | 13 g (27 mmol) of 1,6-bis(5-chloro-1-methyl-4-imidazolesulfonamido)hexane from Example 47 in 250 ml of 1N sodium hydroxide solution are hydrogenated over 3 g of 10% strength Pd/C catalyst while shaking at an initial pressure of 3.45 bar until absorption of hydrogen is complete. After separating off the catalyst, the fi... | Cn1cnc(S(=O)(=O)NCCCCCCNS(=O)(=O)c2cn(C)cn2)c1 | null | null | null |
1,126,782 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH3:12][O:13][C:14](=[O:28])[CH2:15][C:16](=O)[C:17]1[CH:22]=[CH:21][C:20](C(OC)=O)=[CH:19][CH:18]=1>>[CH3:12][O:13][C:14](=[O:28])[C:22]1([NH:9][C:8]2[CH:10]=[CH:11][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[CH:21]=[CH:20][CH:19]=... | COC(=O)CC(=O)c1ccc(C(=O)OC)cc1 | CC(C)Oc1ccc(N)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 sub-title compound was prepared in accordance with step (a) Example 1 from p-isopropoxyaniline and 4-methoxycarbonylbenzoyl acetic acid methyl ester. | COC(=O)C=CC1C=CC=CC1(Nc1ccc(OC(C)C)cc1)C(=O)OC | null | null | null |
1,213,713 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH3:1][N:2]([CH3:26])[C:3]1([C:24]#N)[CH2:8][CH2:7][CH:6]([CH:9]([O:18][CH:19]([O:21][CH2:22][CH3:23])[CH3:20])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5][CH2:4]1.[C:27]1([Mg]Cl)[CH:32]=[CH:31]C=[CH:29][CH:28]=1.[Cl-].[NH4+].O>O1CCCC1>[CH2:22]([O:21][CH:19]([O:18][CH:9]([CH:6]1[CH2:7][CH2:8][C... | CCOC(C)OC(COc1ccccc1)C1CCC(C#N)(N(C)C)CC1 | Cl[Mg]c1ccccc1 | null | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of 1-dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenoxyethyl]cyclohexanecarbonitrile (871 mg, 2.4 mmol) in anhydrous tetrahydrofuran (15 ml) was added dropwise to a 2 M solution of phenylmagnesium chloride in tetrahydrofuran (3.6 ml, 7.3 mmol), while cooling with ice. The mixture was stirred at room temperature ... | CCOC(C)OC(COc1ccccc1)C1CCC(c2ccccc2)(N(C)C)CC1 | null | null | null |
81,970 | ord_dataset-b1023e5ccd7142de9d250aa2e3e124db | null | 1981-01-01T00:06:00 | true | [OH:1][CH:2]([CH:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:25]I.[H-].[Na+].O>CN(C)C=O>[CH3:25][O:1][CH:2]([CH:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:1... | CCOC(=O)C(O)C(Oc1ccccc1[N+](=O)[O-])c1ccccc1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 3 | 1 | To 2 g of ethyl 2-hydroxy-3-phenyl-3-(2-nitro-phenoxy)-propionate dissolved in 30 ml of anhydrous dimethylformamide, CH3I (0.78 ml) was added at 3° C., then, in two additions, at the same temperature, NaH 50% (0.3 g) was added too. The whole was stirred at 3° C. for one hour and at room temperature for one hour, after ... | CCOC(=O)C(OC)C(Oc1ccccc1[N+](=O)[O-])c1ccccc1 | null | 96 | null |
883,379 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | Br[Zn][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[N:4]=1.[CH2:11]([C:13]1[C:17](I)=[C:16]([CH:19]=[O:20])[NH:15][C:14]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:12]>C1COCC1.CN1CCCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH2:11]([C:13]1[C:17]([C:3]2[CH:8]=[CH:7][CH:6]... | COc1cccc([Zn]Br)n1 | CCc1c(C(=O)OC(C)(C)C)[nH]c(C=O)c1I | null | CC(C)(C)[P]([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C | CN1CCCC1 | 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 | 100 | null | Tert-butyl 3-ethyl-5-formyl-4-iodo-1H-pyrrole-2-carboxylate was obtained following the procedures described in Example 1. To a solution of bromo(6-methoxypyridin-2-yl)zinc (0.076 g, 0.30 mmol) in THF (0.6 mL) and N-methylpyrrolidine (0.44 mL) under argon was added Pd(Pt-Bu3)2 (0.002 g, 0.0032 mmol) and tert-butyl 3-eth... | CCc1c(C(=O)OC(C)(C)C)[nH]c(C=O)c1-c1cccc(OC)n1 | null | null | null |
1,757,692 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.Cl[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[CH:17][N:18]=2)[N:15]=1.CC([O-])(C)C.[K+]>O1CCOCC1>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([... | FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1 | OCC1CCOCC1 | null | CC(C)(C)[O-] | [K+] | 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 | 70 | 4 | To the solution of compound (tetrahydro-2H-pyran-4-yl)methanol (100 mg, 0.86 mmol) and compound 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (270 mg, 0.86 mmol) in 10 mL dioxane was added t-BuOK (200 mg, 1.78 mmol). The mixture was stirred at 70° C. for 4 hrs. Then the mixture was purified by Pre-HPL... | FC(F)(F)Oc1cccc(-c2cnc3ccc(OCC4CCOCC4)nn23)c1 | null | 7.4 | null |
1,025,271 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | Cl.[C:2]([O:6][C:7](=[O:39])[CH2:8][C:9](=[O:38])[C:10]([CH3:37])([CH3:36])[C:11](=[O:35])[CH:12]([CH3:34])[CH:13]([O:25][C:26]([O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])=[O:27])[CH:14]([CH3:24])[CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:5])([CH3:4])[CH3:3]>CO>[C:2]([O:6][C:7](=[O:39... | CC(COCc1ccccc1)C(OC(=O)OCC(Cl)(Cl)Cl)C(C)C(=O)C(C)(C)C(=O)CC(=O)OC(C)(C)C | 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 | 17 | A bomb liner was charged with (R)-RuBINAP catalyst (16.8 mg, 10.0 μmol). HCl (555 μL, 0.2N in MeOH) was added and the mixture was then sonicated for 15 sec. Then a solution of 69 (59.4 mg, 0.1 mmol) in MeOH (555 μL) was added and the mixture transferred to a Parr apparatus. The vessel was purged with H2 for 5 min and t... | CC(COCc1ccccc1)C(OC(=O)OCC(Cl)(Cl)Cl)C(C)C(=O)C(C)(C)C(O)CC(=O)OC(C)(C)C | null | 79.6 | null |
170,228 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [C:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:3])[NH2:2].[O:18]1CCOC[CH2:19]1>>[Cl:10][C:7]1[CH:6]=[C:5]2[C:4]([C:1](=[O:3])[NH:2][C:19](=[O:18])[N:11]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1 | CCOC(=O)CNc1cc(Cl)ccc1C(N)=O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 150 | 0.5 | Ethyl N-(2-carbamoyl-5-chlorophenyl)aminoacetate (357 g) and N,N'-carbonyldiimidazole (451 g) were dissolved in 1,4-dioxane (1.5 l) and 1,4-dioxane was concentrated to a bout 0.5 l by distillation. The resulting mixture was stirred at 150° C. for 30 minutes. After cooling, the precipitated crystals were collected by fi... | CCOC(=O)Cn1c(=O)[nH]c(=O)c2ccc(Cl)cc21 | null | null | null |
371,768 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13](O)=[S:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]... | CCCC[C@H](NS(=O)(=O)c1ccc(Cl)cc1)C(O)=S | CCOC(=O)Cc1ccc(N)cc1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | 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 | The procedure described in Example 180 was repeated, except that (S)-2-(4-chlorobenzenesulfonylamino)-4-ethylthiobutanoic acid (695.2 mg) and ethyl 4-aminophenylacetate (380 mg) were condensed in dichloromethane (30 ml) in the presence of N,N'-dicyclohexylcarbodiimide (509.5 mg). The reaction mixture was filtered, and ... | CCCC[C@H](NS(=O)(=O)c1ccc(Cl)cc1)C(=S)Nc1ccc(CC(=O)OCC)cc1 | null | 31.4 | null |
174,868 | ord_dataset-4937da99a6a247eb90fa70f0d2eac3db | null | 1988-01-01T00:07:00 | true | [H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[CH2:19]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH:35]=O)=[CH:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.O>[CH2:19]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH:35]=[CH:10][CH:9]=[... | O=Cc1cn(Cc2ccccc2)c2ccccc12 | CCOC(=O)/C=C/CP(=O)(OCC)OCC | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | To a suspension of 1.08 g (60% reagent, 27 mmol) of sodium hydride in 20 ml of tetrahydrofuran (THF), stirred in an ice bath, was added dropwise 6 ml (6.7 g, 27 mmol) of triethyl 4-phosphonocrotonate. The resulting mixture was stirred for an additional 1 hour in the cooling bath and a solution of 4.2 g (18 mmol) of 1-b... | CCOC(=O)C=CC=Cc1cn(Cc2ccccc2)c2ccccc12 | null | 62 | null |
1,392,014 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[CH2:16]1[O:18][C@@H:17]1[CH2:19]Cl>>[CH3:8][C:2]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][C@H:17]2[CH2:16][O:18]2)=[CH:11][CH:10]=1)([CH3:1])[CH2:3][C:4]([CH3:5])([CH3:6])[CH3:7] | CC(C)(C)CC(C)(C)c1ccc(O)cc1 | ClC[C@@H]1CO1 | null | null | null | null | null | null | null | 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 4-(1,1,3,3-tetramethyl-butyl)-phenol and S-epichlorohydrin employing the procedures as set forth in Step 1 of Example 1. | CC(C)(C)CC(C)(C)c1ccc(OC[C@H]2CO2)cc1 | null | null | null |
339,034 | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | null | 1996-01-01T00:09:00 | true | [K:1].[OH:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:25](O)(=[O:27])[CH3:26].C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>C(OCC)C>[K:1].[C:25]([O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:1... | COC(=O)c1cc(C=Cc2ccc(S(=O)(=O)O)cc2)ccc1O | CC(=O)O | null | O=S(=O)(O)O | [K] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 1.5 | Methyl 2-hydroxy-5-[2-(4-sulfophenyl)ethenyl]benzoate potassium salt (57.5 g, 0.15 mol), acetic acid (35 ml) and acetic anhydride (142 ml) were refluxed until the major part of the solids had dissolved, and then more acetic anhydride (142 ml) and sulfuric acid (1 ml) were added. After boiling for 1.5 h, the mixture was... | COC(=O)c1cc(C=Cc2ccc(S(=O)(=O)O)cc2)ccc1OC(C)=O | null | null | null |
568,285 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | [NH2:1][CH:2]([CH3:15])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH2:13][NH2:14])=[N:9][CH:10]=1.[H-].[Na+]>>[CH3:15][CH:2]1[NH:1][C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH2:13][NH2:14])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1 | CC(N)CCc1ccc(CCCN)nc1 | null | 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 | 100 | null | A solution of the diamine 9-3 (1.87 g, 9.05 mmol) in xylenes (100 mL) was degassed with nitrogen gas then treated with NaH (1.3 g, 54.3 mmol) and then heated to 100° C. for 16 hours. Mass spectrum indicated desired product formed. The mixture was cooled, EtOH added then poured into water and extracted with EtOAc. The o... | CC1CCc2ccc(CCCN)nc2N1 | null | null | null |
1,586,918 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | C([O:4][C:5]1[C:14]2[C:9](=[C:10]([Br:20])[CH:11]=[C:12]([O:16][CH:17]([CH3:19])[CH3:18])[C:13]=2[CH3:15])[CH:8]=[CH:7][N:6]=1)(=O)C.[OH-].[Na+]>CO>[Br:20][C:10]1[CH:11]=[C:12]([O:16][CH:17]([CH3:18])[CH3:19])[C:13]([CH3:15])=[C:14]2[C:9]=1[CH:8]=[CH:7][NH:6][C:5]2=[O:4] | CC(=O)Oc1nccc2c(Br)cc(OC(C)C)c(C)c12 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 5-bromo-8-methyl-7-(propan-2-yloxy)isoquinolin-1-yl acetate (108 g, 0.28 g, 0.83 mmol) in MeOH (2 mL) was added 1M NaOH (2 mL). The reaction mixture was refluxed for 1 hour, then concentrated under vacuum. The residue was diluted in water and the pH was adjusted to 4-5 with 1M HCl. The solution was ext... | Cc1c(OC(C)C)cc(Br)c2cc[nH]c(=O)c12 | null | 85.4 | null |
1,680,064 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:29])(=[O:28])[NH:26][CH3:27])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.O>CN(C=O)C>[CH3:27][N:26]([CH2:3... | CNS(=O)(=O)N1CCN(c2ncnc3c2ccn3C(=O)OC(C)(C)C)CC12CC2 | BrCCCc1ccccc1 | null | O=C([O-])[O-] | [Cs+] | 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 | 35 | 1.5 | 4-(4-Methylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 4) (0.71 mmol) was dissolved in dry DMF (0.5 mL) and added Cs2CO3 (0.85 mmol) and (3-bromo-propyl)-benzene (0.085 mmol). Stirred at 35° C. for 1.5 h and then added H2O (2 mL). Extracted with EtOA... | CN(CCCc1ccccc1)S(=O)(=O)N1CCN(c2ncnc3[nH]ccc23)CC12CC2 | null | null | null |
138,758 | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | null | 1985-01-01T00:12:00 | true | B(F)(F)F.[CH3:5][C:6]([S:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([OH:23])=[C:15]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:14]=1)([CH3:11])[CH2:7]C(=O)C.[C:28]([C:32]1[CH:37]=[C:36]([SH:38])[CH:35]=[C:34]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:33]=1[OH:43])([CH3:31])([CH3:30])[CH3:29]>C1(C)C=CC=C... | CC(=O)CC(C)(C)Sc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 | CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O | null | FB(F)F | 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 | 0.11 Grams of BF3 -etherate is added to a solution of 2.70 grams of the product from (a) and 4.14 grams of 2,6-di-tert- butyl-4-mercaptophenol dissolved in 30 ml of toluene. The mixture is heated at 55°-65° C. for nine hours and 105°-110° C. for three additional hours. The toluene solution is washed with water and drie... | CC(C)(CC(C)(Sc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)Sc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)Sc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 | null | null | null |
181,668 | ord_dataset-2841bde0239a4964a69f490c014a6e43 | null | 1988-01-01T00:12:00 | true | [C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH2:10][CH2:9]2)(=[O:3])[CH3:2]>[O-2].[O-2].[Mn+4].C(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)(=[O:3])[CH3:2] | CC(=O)c1cccc2c1NCC2 | null | null | [Mn+4] | [O-2] | 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 | 5 | To 30 g. (0.186 mole) of 7-acetylindoline in 415 ml. of methylene chloride was added 48.5 g. (0.56 mole) of manganese dioxide and the mixture refluxed through a soxhlet filled with 4A molecular sieves for 22 hours. The mixture was cooled and an additional 48.5 g. of manganese dioxide was added. Fresh molecular sieves w... | CC(=O)c1cccc2cc[nH]c12 | null | 76 | null |
456,452 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | [Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].Br[CH2:18]/[CH:19]=[CH:20]/[CH3:21]>C(O)C>[C:2]([NH:5][C:6]([CH2:18]/[CH:19]=[CH:20]/[CH3:21])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3] | CCOC(=O)C(NC(C)=O)C(=O)OCC | C/C=C/CBr | null | [Na] | 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 | 8 | 3.86 g (168 mmol) of sodium metal were dissolved in 106 ml of anhydrous ethanol. 36.35 g (168 mmol) of diethyl acetamidomalonate dissolved in 225 ml of anhydrous ethanol were added and the mixture was heated under reflux for 10 minutes. 22.66 g (168 mmol) of (E)-1-bromo-2-butene were added dropwise at room temperature ... | C/C=C/CC(NC(C)=O)(C(=O)OCC)C(=O)OCC | null | 87.8 | null |
622,829 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [CH3:1][O:2][C:3]([C:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[N:9]([C:19]([NH:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:20])[C:8](=[O:29])[NH:7][C:6]=1[CH2:30][O:31][CH3:32])=[O:4].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[C... | CCOC(=O)CCNC(=O)N1C(=O)NC(COC)=C(C(=O)OC)[C@@H]1c1ccc(F)c(F)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 4.5 | (+)-5-Methoxycarbonyl-4-methyoxymethyl-1,2,3,6-tetrahydro-2-oxo-6(S)-(3,4-difluorophenyl)-1-[(2-ethoxycarbonylethylamino)carbonyl]pyrimidine (168 mg, 0.37 mmol) was dissolved in 5 mL of methanol. A 2.0M solution of aqueous sodium hydroxide (400 mL, 0.80 mmol) was added dropwise. The mixture was stirred at ambient tempe... | COCC1=C(C(=O)OC)[C@H](c2ccc(F)c(F)c2)N(C(=O)NCCC(=O)O)C(=O)N1 | null | null | null |
714,893 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [OH:1][N:2]1[C:6]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[CH:5][CH:4]=[N:3]1.[CH3:12][N:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14](Cl)=[O:15]>>[S:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:6]1[N:2]([O:1][C:14](=[O:15])[N:13]([CH3:12])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=[CH:4][CH:5]=1 | On1nccc1-c1cccs1 | CN(C(=O)Cl)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 | The title compound was prepared from 1-hydroxy-5-(2-thienyl)pyrazole and N-methyl-N-phenylcarbamoyl chloride applying the general procedure 8. The crude product was purified by flash chromatography (Quad flash 12, EtOAc-heptane) (51%, crystals). | CN(C(=O)On1nccc1-c1cccs1)c1ccccc1 | null | null | null |
546,551 | ord_dataset-d31180f42ced44719fd9e72685c798bf | null | 2002-01-01T00:05:00 | true | CS([C:5]1[N:10]=[C:9]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH2:23][CH2:24][CH3:25])[NH:13][C:14](=[O:15])[C:8]2=[CH:7][N:6]=1)(=O)=O.Cl.[CH2:27]([O:29][C:30](=[O:33])[CH2:31][NH2:32])[CH3:28].C(N(CC)CC)C>ClCCl>[CH2:27]([O:29][C:30]([CH2:31][NH:32][C:5]1[N:10]=[C:9]2[N:11]=[C:12]([C:16]3[CH:... | CCOC(=O)CN | CCCOc1ccccc1-c1nc2nc(S(C)(=O)=O)ncc2c(=O)[nH]1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | In a similar manner to Example 57 reaction of 7-methylsulphonyl-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine (0.86 g), glycine ethyl ester hydrochloride (0.65 g) and triethylamine (0.47 g) in dichloromethane (15 ml) yielded the title compound, 0.38 g, m.p. 174.5-176° C. (recrystallized from ethanol:wa... | CCCOc1ccccc1-c1nc2nc(NCC(=O)OCC)ncc2c(=O)[nH]1 | null | null | null |
904,308 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:24])=[C:9]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:38][C:39]#[N:40]>CC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]... | Cc1c(-c2ccccc2)n(Cc2ccccc2)c2cccc(-c3ccc(O)cc3)c12 | N#CCBr | 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 | null | null | The desired product was prepared using a procedure similar to step 5 of example 3. Thus, 4-(1-benzyl-3-methyl-2-phenyl-1H-indol-4-yl)-phenol (0.260 g, 0.668 mmol) was reacted with K2CO3 (0.111 g, 0.802 mmol) and bromoacetonitrile (0.096 g, 0.802 mmol) in acetone (5 ml) to give the product (0.271 g, 0.633 mmol, 95%) as ... | Cc1c(-c2ccccc2)n(Cc2ccccc2)c2cccc(-c3ccc(OCC#N)cc3)c12 | null | null | null |
51,616 | ord_dataset-8881493772e04c4b9495fc2114379967 | null | 1979-01-01T00:02:00 | true | [NH2:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1.[N+]([NH:13][C:14](N)=[O:15])([O-])=O>>[NH2:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:14]([NH2:13])=[O:15])[CH2:6]1 | NCCOC1CCNC1 | NC(=O)N[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Generally speaking, the reaction of a 3-aminoethoxypyrrolidine II with nitrourea to give a 3-aminoethoxypyrrolidine-1-carboxamide I is run in a lower alkanol solvent, e.g., ethanol, usually at or below reflux temperature for a period of time of from about 4 hours to about 18 hours. The reaction of a 3-aminoethoxypyrrol... | NCCOC1CCN(C(N)=O)C1 | null | null | null |
718,899 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([O:26][C:27]4[CH:28]=[C:29]5[C:33](=[CH:34][CH:35]=4)[NH:32][C:31]([CH3:36])=[CH:30]5)=[N:21][CH:22]=[N:23]3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:36][C:31]1[NH:32][C:33]2[C:29]([CH:30]=1)=[CH:28][... | Cc1cc2cc(Oc3ncnc4cc(OCC5CCN(C(=O)OC(C)(C)C)CC5)ccc34)ccc2[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | A suspension of 7-(1-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-(2-methylindol-5-yloxy)quinazoline (150 mg, 0.31 mmol), (prepared as described in Example 90), in methylene chloride (2 ml) and TFA (1.5 ml) was stirred for 1 hour at ambient temperature. After removal of the volatiles under vacuum the residue was azeotro... | Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1 | null | 66.4 | null |
161,217 | ord_dataset-e402405fd21e4770a14f157cb62ca439 | null | 1987-01-01T00:07:00 | true | [C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1>ClCCl>[N:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:12][CH:13]=1 | Cc1ccncc1 | O=C(Cl)c1ccccc1 | 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 | 10 | 16 | 30.2 g of benzoyl chloride dissolved in 30 cc of dichloromethane was added dropwise over 1 hour to 10 g of 4-methylpyridine dissolved in 60 cc dichloromethane and maintained at 10° C. during the addition. The reaction was brought to room temperature and stirred 16 hours. The reaction was brought to reflux for 1 hour, t... | O=C(Cc1ccncc1)c1ccccc1 | null | null | null |
1,637,259 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:8]=2)=[N:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23].[C:24](OC(=O)C)(=[O:26])[CH3:25].S(=O)(=O)(O)O>>[C:24]([NH:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:8]=2)=[N:... | CC(=O)OC(C)=O | CC(=O)Nc1cc(-c2nc(-c3ccccc3Cl)c(N)s2)ccn1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 18 | To a stirred solution of N-{4-[5-amino-4-(2-chlorophenyl)-1,3-thiazol-2-yl]pyridin-2-yl}acetamide (0.020 g, 0.058 mmol) in anhydrous acetic anhydride (1.00 mL, 10.60 mmol) was added dropwise concentrated sulfuric acid (0.002 mL, 0.030 mmol) and stirred for 18 h. The reaction was quenched by the dropwise addition of a t... | CC(=O)Nc1cc(-c2nc(-c3ccccc3Cl)c(NC(C)=O)s2)ccn1 | null | 62.4 | null |
393,752 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [CH3:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[CH:17]=[C:16]([F:22])[C:3]=1[C:4]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[F:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1>>[CH3:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[CH:17]=[C:16]([F:22])[C:3]=1[C:4]([C:6](=[CH:12][NH:28][C:27]1[CH:29]=[CH:30]... | Nc1ccc(F)cc1 | CCOC=C(C(=O)OCC)C(=O)c1c(F)cc(F)c(F)c1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and p-fluoroaniline (0.39 g), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(4-fluorophenyl)aminoacrylate, which is then treated with 60% sodium hydride (0.15 g) as in Reference Example 9 ... | CCOC(=O)C(=CNc1ccc(F)cc1)C(=O)c1c(F)cc(F)c(F)c1C | null | null | null |
1,452,532 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=1.C1C=C[C:19]2N(O)N=[N:22][C:20]=2[CH:21]=1.C(Cl)CCl.C1(N)CC1>ClCCl>[CH:20]1([NH:22][C:13]([C:10]2[CH:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[O:12][N:11]=2)=[O:15])[CH2:21][CH2:19]1 | O=C(O)c1cc(-c2ccccc2O)on1 | On1nnc2ccccc21 | null | NC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | ClCCCl | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a 20 mL flask was added the crude acid from step 3 (20 mg, 0.1 mmol), HOBt (16 mg, 0.12 mmol), and EDC (23 mg, 0.12 mmol). To this was added dichloromethane (3 mL) and the resulting heterogeneous mixture was stirred for 30 minutes at room temperature. To the resulting solution was added cyclopropylamine (9.0 mg, 0.1... | O=C(NC1CC1)c1cc(-c2ccccc2O)on1 | null | 25 | null |
1,310,950 | 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.[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:32]=2)[CH2:27][CH2:26]1>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]... | Cc1nn(C)cc1-n1c(=O)n(C)c2cnc3ccc(Br)cc3c21 | CN1CCc2cc(B3OC(C)(C)C(C)(C)O3)ccc21 | null | null | null | null | null | null | null | 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, 40 mg, 0.106 mmol) and 1-methylindoline-5-boronic acid pinacol ester (Maybridge, Basel, Switzerland, 34 mg, 0.127 mmol) to... | Cc1nn(C)cc1-n1c(=O)n(C)c2cnc3ccc(-c4ccc5c(c4)CCN5C)cc3c21 | null | null | null |
104,223 | ord_dataset-b2a00a09c8494aaf9348c3a3af29d26e | null | 1983-01-01T00:04:00 | true | [CH2:1]([O:8][CH2:9][CH2:10][C:11](=O)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([S:25]([CH3:27])=[O:26])[CH:19]=1)[OH:17].C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([NH:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:... | CS(=O)c1cc(C(O)CN)ccc1O | CC(=O)CCOCc1ccccc1 | null | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 16 | Combine 4-benzyloxy-2-butanone (1.78 g, 10 mmol) with 2-amino-1-(4-hydroxy-3-methylsulfinylphenyl)ethanol (10 mmol) in methanol (50 ml) and add sodium cyanoborohydride (0.63 g, 10 mmol). Let stand 16 hours, concentrate the solution and purify the crude product by chromatography on silica gel using chloroform: methanol:... | CC(CCOCc1ccccc1)NCC(O)c1ccc(O)c(S(C)=O)c1 | null | null | null |
1,147,939 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH3:8].C([Li])CCC.CN([CH:17]=[O:18])C.Cl>C1COCC1.O>[CH2:7]([C:6]1[CH:5]=[CH:4][S:3][C:2]=1[CH:17]=[O:18])[CH3:8] | CCc1ccsc1Br | CN(C)C=O | null | Cl | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | -75 | 1 | A solution of 3-ethyl-thiophene (12.14 g, 54.4 mmol) in acetonitrile (60 mL) is cooled to 10° C. before a solution of N-bromo-succinimide (9.31 g, 52.3 mmol) in acetonitrile (90 mL) is added dropwise. The reaction is slightly exothermic. The mixture is stirred and warmed to rt. Another portion of N-bromo-succinimide (2... | CCc1ccsc1C=O | null | 88.6 | null |
531,753 | ord_dataset-7774db17e619477ea20ee621abe71257 | null | 2002-01-01T00:01:00 | true | [C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:49]=[CH:50][C:51]=1[Cl:52])[CH2:8][O:9][CH:10]1[O:15][CH:14]([CH2:16][O:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:13]([O:28][CH:29]2[O:38][CH:37]3[CH:32]([O:33][CH:34]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[O:35][CH2:36]3)[CH:31]([OH:... | COc1ccc(C(=O)OCC2OC(OCc3ccc(Cl)c(NC(C)=O)c3)C(O)C(O)C2OC2OC3COC(c4ccccc4)OC3C(O)C2O)cc1 | null | null | [Br-] | [K+] | 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 | The title compound was prepared as a white foam (0.142 g, 81%) from 4-methoxy-benzoic acid 6-(3-acetylamino-4-chloro-benzyloxy)-3-(7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester using a procedure similar to Example 25, mp >110° C. (decomp.); 1H NMR (DM... | COc1ccc(C(=O)OCC2OC(OCc3ccc(Cl)c(NC(C)=O)c3)C(OC(C)=O)C(OC(C)=O)C2OC2OC3COC(c4ccccc4)OC3C(OC(C)=O)C2OC(C)=O)cc1 | null | null | null |
1,359,720 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][CH:16]([F:18])[F:17])(=O)=O)=CC=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@H:26]2[C@H:31]([OH:32])[C@@H:30]([OH:33])[C@H:29]([OH:34])[C@@H:28]([CH2:35][OH:36])[O:27]2)=[CH:22][C:21]=1[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O... | Cc1ccc(S(=O)(=O)OCCOCC(F)F)cc1 | OC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(O)cc3)c2)[C@H](O)[C@@H](O)[C@@H]1O | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 48 | 2-(2,2-difluoroethoxy)ethyl 4-methylbenzenesulfonate (53 mg, 0.19 mmol) dissolved in anhydrous DMF (3 mL) was added to a reaction flask containing (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (intermediate D1) (57 mg, 0.15 mmol) in DMF (3 mL) at room temperatu... | OC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(OCCOCC(F)F)cc3)c2)[C@H](O)[C@@H](O)[C@@H]1O | null | 6.3 | null |
1,368,206 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[CH:21]([S:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27])([CH3:23])[CH3:22].C(OCC)(=O)C>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2... | CC(C)Sc1ccccc1N | COc1ccc(Cn2nnc3c(Cl)nc(Cl)nc32)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 5,7-dichloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (0.03 g) and 2-(isopropylthio)aniline (0.1 g) in dioxane (10 mL) was heated at 100° C. for 10 h. It was then cooled down to room temperature and ethyl acetate (20 mL) was added. The mixture was washed with saturated sodium bicarbonate (1... | COc1ccc(Cn2nnc3c(Nc4ccccc4SC(C)C)nc(Cl)nc32)cc1 | null | null | null |
978,486 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](Cl)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][C:19]([N:28]([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.N1C=CC=CC=1>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:12])[NH:14][CH2:15][CH:16]... | O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 | CN(C)C1(c2ccccc2)CCC(CN)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 20 | The chloroformic acid 4-nitrophenyl ester (913.5 mg, 4.53 mmole) dissolved in abs. DCM (15 ml) was slowly added dropwise while cooling in ice water to a solution of (4-aminomethyl-1-phenylcyclohexyl)-dimethylamine (1 g, 4.3 mmole) in abs. DCM (15 ml) and pyridine (766 μl, 9.49 mmole). The reaction mixture was then stir... | CN(C)C1(c2ccccc2)CCC(CNC(=O)Oc2ccc([N+](=O)[O-])cc2)CC1 | null | null | null |
1,226,982 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=1>S(Cl)(Cl)=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21... | O=C(O)c1cc([N+](=O)[O-])ccc1Cl | CCOC(=O)Cc1ccc(N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | O | null | null | null | null | null | null | null | null | null | 60 | 18 | 2-Chloro-5-nitrobenzoic acid (1.99 g, 9.87 mmol) was stirred for 18 hrs at 60° C. in thionyl chloride (10 ml). The excess thionyl chloride was removed by evaporation and the crude oil dissolved in chloroform (20 ml). To this solution was added ethyl (4-aminophenyl)acetate (1.18 g, 6.58 mmol) and the reaction was stirre... | CCOC(=O)Cc1ccc(NC(=O)c2cc([N+](=O)[O-])ccc2Cl)cc1 | null | null | null |
739,769 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | C(O[C:6](=O)[N:7](C)[CH2:8][C:9](=[O:31])[NH:10][C:11]1[CH:12]=[C:13]2[C:29](=[O:30])[NH:28][N:27]=[CH:26][C:15]3=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:17][C:18]([CH:19]=1)=[C:14]23)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>C(Cl)Cl>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].... | CN(CC(=O)Nc1cc2c3c(c(-c4ccccc4)[nH]c3c1)C=NNC2=O)C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | 0.5 | The title compound of Example 19 (19 mg, 0.042 mmol) in CH2Cl2 (0.65 mL) was treated with trifluoroacetic acid (0.45 mL) and allowed to stir for 0.5 hours. The volatile components were removed under vacuum, and diethyl ether was added and evaporated three times to give the title compound (19 mg, 0.041 mmol) as a yellow... | CNC(C)C(=O)Nc1cc2c3c(c(-c4ccccc4)[nH]c3c1)C=NNC2=O | null | 98 | null |
1,175,827 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | C([Mg]Cl)(C)C.[O:6]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:8]=[CH:7]1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH:29]=[O:30])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH:29]([OH:30])[C:7]2[O:6][C:14]3[CH:13]=[CH:1... | c1cc2ocnc2cn1 | CC(C)(C)OC(=O)N1CCC(CC=O)CC1 | null | CC(C)[Mg]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 20 | 1 | i-PrMgCl (0.44 mL of a 2 mmol/mL solution in THF, 0.88 mmol) was added dropwise to a stirred solution of oxazolo[4,5-c]pyridine (105 mg, 0.87 mmol) in anhydrous THF (3 mL) at 0° C. After 1 h, a solution of 4-(2-oxo-ethyl)piperidine-1-carboxylic acid tert-butyl ester (198 mg, 0.87 mmol) in anhydrous THF (2 mL) was added... | CC(C)(C)OC(=O)N1CCC(CC(O)c2nc3cnccc3o2)CC1 | null | null | null |
837,481 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([S:25]([NH:28][C@H:29]([C:33]([OH:35])=[O:34])[CH:30]([CH3:32])[CH3:31])(=[O:27])=[O:26])=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)=[O:11])=[CH:7][C:6]=2[CH:36]=1.[C:37]1([S:43](Cl)(=[O:45])=[O:44])[CH:42]=[CH:4... | CC(C)[C@H](NS(=O)(=O)c1ccc(-c2ccc(NC(=O)c3cc4cc(N)ccc4o3)cc2)cc1)C(=O)O | O=S(=O)(Cl)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 | N-[(4′-{[(5-amino-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valine-Wang resin (0.3 g), from Example 7, was sulfonylated with benzenesulfonyl chloride according to the procedure of Example 8 followed by cleavage from the resin to provide 4′-[(5-benzenesulfonylamino-benzofuran-2-carbonyl)-amino]-bi... | CC(C)[C@H](NS(=O)(=O)c1ccc(-c2ccc(NC(=O)c3cc4cc(NS(=O)(=O)c5ccccc5)ccc4o3)cc2)cc1)C(=O)O | null | null | null |
1,300,687 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [Cl:1][C:2]1[N:3]=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=3)[C:14]([OH:16])=O)=[CH:8][C:6]=2[N:7]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:5]2[S:10][C:9]([C:11]... | C1COCCN1 | O=C(O)c1cccc(-c2cc3nc(Cl)nc(N4CCOCC4)c3s2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzoic acid (49 mg) was reacted with morpholine via General Procedure B to yield 3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl(morpholino)methanone. Crude 3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl(morpholino)methanone (58 mg) was coupled... | O=C(c1cccc(-c2cc3nc(Cl)nc(N4CCOCC4)c3s2)c1)N1CCOCC1 | null | null | null |
244,907 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | [CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[N:4]([N:12]([CH2:19][CH2:20][CH3:21])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28]([N:35]=[C:36]=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[C:29]1([CH2:28][NH:35][C:36](=[O:37])[O:11][C:8]2[CH... | CCCN(c1ccncc1)n1cc(C)c2cc(O)ccc21 | O=C=NCc1ccccc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution consisting of 3-methyl-1-(propyl-4-pyridinylamino)-1H-indol-5-ol (1.80 g) and tetrahydrofuran (43 ml) were added with stirring at room temperature milled potassium carbonate (0.93 g) and benzyl isocyanate (0.87 ml). Stirring was continued under nitrogen for 16 hours. The mixture was filtered through a pad... | CCCN(c1ccncc1)n1cc(C)c2cc(OC(=O)NCc3ccccc3)ccc21 | null | null | null |
1,033,524 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH3:34])[N:14]([CH2:15][C:16]([O:18]CC)=[O:17])[C:13](=[O:21])[C:12]3([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[N:11]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[Li+:35].[OH-].Cl>C1COCC1.O>[C:30]([O:29][C:27]([N:11]1[C:12]2([CH2:22][C... | CCOC(=O)CN1C(=O)C2(CCCCC2)N(C(=O)OC(C)(C)C)C[C@@]1(C)c1cc(F)cc(F)c1 | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of tert-butyl (3R)-3-(3,5-difluorophenyl)-4-(2-ethoxy-2-oxoethyl)-3-methyl-5-oxo-1,4-diazaspiro[5.5]undecane-1-carboxylate from Step I (65 mg, 0.135 mmol) in THF (1.5 mL) and H2O (0.5 mL) was added 1 N aqueous LiOH (0.14 mL, 0.14 mmol) and the resulting mixture was stirred at ambient temperature for 1 h. ... | CC(C)(C)OC(=O)N1C[C@@](C)(c2cc(F)cc(F)c2)N(CC(=O)[O-])C(=O)C12CCCCC2 | null | null | null |
870,949 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | Cl.[F:2][CH:3]([F:32])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25].[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>>[CH:33]1([C:36]([N:29]2[CH2:28][CH2:2... | O=C(Cl)C1CC1 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and cyclopropanoyl chloride. Off-white solid. MS (m/z): 503.2 (M+H)+. | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)C4CC4)CC2)n3CC(F)F)CC1 | null | null | null |
614,091 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23]>O1CCCC1>[CH2:29]([Sn:24]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:25][CH2:26][CH2:27][CH3:28])[C:2]1[N:6]2... | FC(F)(F)c1ccn2c(Br)cnc2n1 | CCCC[Sn](Cl)(CCCC)CCCC | null | CC(C)[Mg]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 0.17 | To a cooled (−78° C.) solution of 3-bromo-7-trifluoromethyl-imidazo[1,2-a]pyrimidine (1.0 g, 3.78 mmol) in tetrahydrofuran (20 ml) was added isopropylmagnesium chloride (2.08 ml of a 2.0M solution in tetrahydrofuran, 4.16 mmol). After stirring for 5 min tributyltin chloride (1.2 ml, 4.42 mmol) was added and the reactio... | CCCC[Sn](CCCC)(CCCC)c1cnc2nc(C(F)(F)F)ccn12 | null | null | null |
1,256,305 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[O:16][C:15]([CH3:17])=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[O:16][C:15]([CH3:17])=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1 | COc1c(-c2cc(C(=O)O)c(C)o2)cccc1[N+](=O)[O-] | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 5-(2-Methoxy-3-nitro-phenyl)-2-methyl-furan-3-carboxylic acid 53c (450 mg, 1.62 mmol) was dissolved in methanol, followed by addition of 45 mg of palladium on carbon. The reaction mixture was heated to reflux for 4 hours under hydrogen atmosphere. The reaction was monitored by TLC until the disappearance of the startin... | COc1c(N)cccc1-c1cc(C(=O)O)c(C)o1 | null | 92.4 | null |
1,613,500 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21]([NH2:23])=O)=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[C:5]2[S:6][CH:7]=[CH:8][N:4]2[N:3]=1.COC1C=CC(P2(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:33]2)=CC=1.CCOC(C)=O.Cl>COCCOC>[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21](=[S:33])[NH2:23])=[C:13]([C:15]3[CH:20]=[... | Cc1nn2ccsc2c1-c1nc(-c2ccccc2)c(C(N)=O)s1 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 80 | 1 | To a suspension of 2-(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)-4-phenyl-1,3-thiazole-5-carboxamide (340 mg, 1.0 mmol) obtained above in DME (10 mL) was added 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (485 mg, 1.2 mmol), and the mixture was stirred at 80° C. for 1 h. The reaction mixture was all... | Cc1nn2ccsc2c1-c1nc(-c2ccccc2)c(C(N)=S)s1 | null | 48.2 | null |
1,416,368 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | C(O[C:5](=[O:22])[NH:6][CH:7]1[CH2:11][C:10](=[O:12])[O:9][CH:8]1[O:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18]C=1)C=C.[N:23]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][CH2:28][C@H:24]1C(O)=O>>[C:34]([O:33][C:31]([N:23]1[CH2:30][CH2:29][CH2:28][CH:24]1[C:5](=[O:22])[NH:6][CH:... | C=CCOC(=O)NC1CC(=O)OC1OCCc1ccccc1 | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from 40 (1.16 g, 4.0 mmol) and Boc-Pro-OH according to the procedure used to prepare 100 (Scheme XVIII) to afford 1.53 g (94% yield) of the title compound as a white solid. 1H-NMR (500 MHz, CDCl3): δ 1.61 (br, 9H), 1.88 (br, 2H), 2.00-2.50 (m, 3H), 2.80-3.10 (m, H), 3.20-3.60 (m, 2H), 4.05-4.45 (m, 1.5H), 4.58... | CC(C)(C)OC(=O)N1CCCC1C(=O)NC1CC(=O)OC1OCc1ccccc1 | null | 94 | null |
759,226 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[N:8]=[C:7]2[C:20]1[NH:21][CH:22]=[CH:23][CH:24]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([O:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[N:8]=[C:7]2[C:20]1[NH:... | CC(C)(C)C(=O)On1nc(-c2ccc[nH]2)c2cc([N+](=O)[O-])ccc21 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 2,2-Dimethyl-propionic acid 5-nitro-3-(1H-pyrrol-2-yl)-indazol-1-yl ester (370 mg, 1.13 mmol) (from Example 28) was hydrogenated using 10% Pd/C in ethanol (35 mL) at room temperature for 2 hours. The reaction was filtered and the filtrate was concentrated to give 2,2-dimethyl-propionic acid 5-amino-3-(1H-pyrrol-2-yl)-i... | CC(C)(C)C(=O)On1nc(-c2ccc[nH]2)c2cc(N)ccc21 | null | null | null |
1,504,042 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [C:1]([O:5][C:6](=[O:25])/[CH:7]=[CH:8]/[C:9]1[S:10][C:11]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[CH:12][C:13]=1[CH3:14])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:25])[CH2:7][CH2:8][C:9]1[S:10][C:11]([C:15]([OH:17])=[O:16])=[CH:12][C:13]=1[CH3:14])([CH3:4])([CH3:2])[CH3:3] | Cc1cc(C(=O)OCc2ccccc2)sc1/C=C/C(=O)OC(C)(C)C | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | (E)-3-(5-Benzyloxycarbonyl-3-methylthiophen-2-yl)-2-propenoic acid tert-butyl ester (1.42 g, 4.12 mmol) obtained in step 3 was dissolved in ethanol (12 mL), 10% palladium/carbon (142 mg) was added, and the mixture was stirred at room temperature overnight under a hydrogen atmosphere. After completion of the reaction, p... | Cc1cc(C(=O)O)sc1CCC(=O)OC(C)(C)C | null | 91.5 | null |
1,721,146 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH3:34][C@H:35]1[C:43]2[C:42]([CH:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)=[N:41][CH:40]=[N:39][C:38]=2[CH2:37][CH2:36]1.[C:50]([O:54][C:55]([N:57]1[C:61]([CH3:63])([CH3:62])[CH2:60][CH2:59][C@H:58]1[C@H:64]([C:68]1[CH:73]=[CH:72][C:71]([Cl:... | CC(C)(C)OC(=O)N1[C@H]([C@@H](C(=O)O)c2ccc(Cl)cc2)CCC1(C)C | C[C@@H]1CCc2ncnc(C3CCNCC3)c21 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | DIPEA (174 μL, 1.00 mmol) and O-(benzotriazol-1yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (25 mg, 0.065 mmol) were added to a solution of (R)-5-methyl-4-(piperidin-4-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (22 mg, 0.10 mmol) and (S)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)-2-(4-chlorophe... | C[C@@H]1CCc2ncnc(C3CCN(C(=O)[C@@H](c4ccc(Cl)cc4)[C@@H]4CCC(C)(C)N4C(=O)OC(C)(C)C)CC3)c21 | null | 84.9 | null |
303,928 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | [O:1]([CH:5]([CH3:16])[CH2:6][O:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[N+:2]([O-:4])=[O:3].[NH2:17][C@H:18]([C:21]([OH:23])=[O:22])[CH2:19][SH:20]>>[C:21]([CH:18]1[CH2:19][S:20][CH:10]([C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[O:7][CH2:6][CH:5]([O:1][N+:2]([O-:4])=[O:3])[CH3:16])[NH:17]1)([OH:23])=[O... | N[C@@H](CS)C(=O)O | CC(COc1ccccc1C=O)O[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from 2-(2-nitroxypropoxy)benzaldehyde and cysteine as described in Example XVI. Yield: 30%. Empirical formula: C13H16N2O6S. Molecular weight: 328. Melting point: 127°-130° C. | CC(COc1ccccc1C1NC(C(=O)O)CS1)O[N+](=O)[O-] | null | 30 | null |
310,331 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18]>C1COCC1>[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13] | O=[N+]([O-])c1cnc2ccccc2c1Cl | Cc1ccccc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 4-Chloro-3-nitroquinoline (J. Med. Chem. 1974, 17, 245) (2.08 g, 0.01 mol) and 2-methylaniline (2.14 g, 0.02 mol) were dissolved in THF (50 ml) and the mixture stirred at reflux for 16 hours, during which time a pale yellow solid was deposited. After cooling, the solvent was evaporated and the residue dissolved in 2M H... | Cc1ccccc1Nc1c([N+](=O)[O-])cnc2ccccc12 | null | 43 | null |
1,635,606 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | CS([O:5][CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)(=O)=O.O[C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][O:32][C:33]3[CH:46]=[CH:45][C:36]4[C@H:37]([CH2:40][C:41]([O:43][CH3:44])=[O:42])[CH2:38][O:39][C:35]=4[CH:34]=3)[CH:26]=2)=[C:20]([CH3... | CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)C1 | COC(=O)C[C@@H]1COc2cc(OCc3cccc(-c4c(C)cc(O)cc4C)c3)ccc21 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 80 | 12 | tert-Butyl 3-((methylsulfonyl)oxy)azetidine-1-carboxylate 14a (100 mg, 0.40 mmol, prepared by a method disclosed in PCT patent application WO2011097958”), (S)-methyl 2-(6-((4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3 h (80 mg, 0.19 mmol) and cesium carbonate (130 mg, 0.40 mmol) ... | COC(=O)C[C@@H]1COc2cc(OCc3cccc(-c4c(C)cc(OC5CN(C(=O)OC(C)(C)C)C5)cc4C)c3)ccc21 | null | 50 | null |
1,222,831 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [CH2:1]([CH2:3][NH2:4])[OH:2].[Cl:5][C:6]1[CH:10]=[C:9]([C:11](Cl)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[Cl:5][C:6]1[CH:10]=[C:9]([C:11]([NH:4][CH2:3][CH2:1][OH:2])=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15] | COC(=O)c1[nH]c(C(=O)Cl)cc1Cl | NCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | Ethanolamine (0.175 mL, 2.90 mmol) was added to a solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.150 g, 0.580 mmol) in THF and the resulting solution stirred until no starting material was evident by TLC. Purification was accomplished by silica gel column chromatography (30-100% EtOAc/hexane... | COC(=O)c1[nH]c(C(=O)NCCO)cc1Cl | null | 57.3 | null |
130,187 | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | null | 1985-01-01T00:05:00 | true | Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:14][C:13](=[O:15])[O:12][C:11]([CH3:17])([CH3:16])[C:10]=2[CH:18]=1.[CH:19]1([C:25]2[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH:19]1([C:25]2[CH:26]=[CH:27][C:28]([S:31][CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:7]=[CH:8... | Sc1ccc(C2CCCCC2)cc1 | CC1(C)OC(=O)Nc2ccc(OCCCCl)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 | Prepared analogously to Example 1 from 6-(3-chloropropoxy)-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4-cyclohexyl-thiophenol. | CC1(C)OC(=O)Nc2ccc(OCCCSc3ccc(C4CCCCC4)cc3)cc21 | null | null | null |
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