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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
66,724 | ord_dataset-b5f1497361c94e5fa55257200189a6a4 | null | 1980-01-01T00:06:00 | true | [CH3:1][C:2]1([C:17]([O:19]CC)=[O:18])[N:3]2[CH:6]([O:7]/[C:8]/1=[CH:9]\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][C:4]2=[O:16].[OH-].[Na+:23]>C1COCC1>[CH3:1][C:2]1([C:17]([O-:19])=[O:18])[N:3]2[CH:6]([O:7]/[C:8]/1=[CH:9]\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][C:4]2=[O:16].[Na+:23] | CCOC(=O)C1(C)/C(=C/c2ccccc2)OC2CC(=O)N21 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 2 | Ethyl (Z)-2-methyl-3-benzylidene-7-oxo-4-oxa-1-azabicyclo[3.2.0]-heptane-2-carboxylate (0.05 g, 0.174 mmole) was dissolved in 2 ml THF/2 ml H2O, ice cooled and treated with 1 N NaOH (0.174 ml). After 2 hours the solution was ether washed, brought to pH 7 with dil. HCl and freeze dried to yield the title compound (82%) ... | CC1(C(=O)[O-])/C(=C/c2ccccc2)OC2CC(=O)N21 | null | 82 | null |
251,977 | ord_dataset-49bd993346b64eeeb2a8fe2643164a0a | null | 1992-01-01T00:08:00 | true | [CH3:1][C:2]([C:5]1[CH:26]=[CH:25][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[OH-].[Na+].Cl>>[CH3:4][C:2]([C:5]1[CH:26]=[CH:25][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:1... | CCOC(=O)COc1ccc(NC(=O)c2ccc(C(C)(C)C)cc2)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2.0 g. 4-(1,1-Dimethylethyl)-N-[4-(ethoxycarbonylmethoxy)-phenyl]-benzamide (Example 31) are heated in 20 ml. 2N aqueous sodium hydroxide solution, then acidified with concentrated hydrochloric acid, filtered off with suction and washed with water. After recrystallisation from ethyl acetate, there is obtained 1.2 g. (6... | CC(C)(C)c1ccc(C(=O)Nc2ccc(OCC(=O)O)cc2)cc1 | null | null | null |
1,081,779 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[CH3:9][C@H:10]1[CH2:15][NH:14][C@H:13]([CH3:16])[CH2:12][N:11]1[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=2)[N:22]=1>>[CH3:9][C@H:10]1[CH2:15][N:14]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C@H:13]([CH3:16])[CH2:12][N:1... | O=Cc1cccnc1 | C[C@@H]1CN(c2ccc3nnc(C(F)(F)F)n3n2)[C@@H](C)CN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of pyridine-3-carboxaldehyde and 6-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine was allowed to react by General Synthetic Method 5 to give 6-[(2S,5R)-2,5-dimethyl-4-(pyridin-3-ylmethyl)piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine in 84% yield... | C[C@@H]1CN(c2ccc3nnc(C(F)(F)F)n3n2)[C@@H](C)CN1Cc1cccnc1 | null | 84 | null |
1,737,702 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=2.[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>>[C:16]1([C:3]2[C:2]([C:28]3[CH:29]=[CH:30][C:25]([O:24][C:23]([F:35])([F:34])[F:22])=[CH:26... | COC(=O)c1ccc2nc(-c3ccccc3)c(Br)nc2c1 | OB(O)c1ccc(OC(F)(F)F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product was obtained via a Suzuki coupling reaction using the method previously shown in Example 20, Step 3, using methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (100 mg, 0.29 mmol, 1.00 equiv) and 4-(trifluoromethoxy)phenylboronic acid (89.6 mg, 0.43 mmol, 1.50 equiv) as reactants. Purification via silica gel co... | O=C(O)c1ccc2nc(-c3ccccc3)c(-c3ccc(OC(F)(F)F)cc3)nc2c1 | null | 47.9 | null |
1,674,192 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](Cl)=[C:11]1[C:6]([CH:7]=[CH:8][C:9]([O:17][CH3:18])=[CH:10]1)=[N:5]2.[N:19]1([CH2:24][CH2:25][CH2:26][CH2:27][NH2:28])[CH2:23][CH2:22][CH2:21][CH2:20]1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:28][CH2:27][CH2:26][CH2:25][CH2:24][N:19]1[CH2:23... | COc1ccc2nc3cc(Cl)ccc3c(Cl)c2c1 | NCCCCN1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the general procedure of Example 1 and making non-critical variations, but using 6,9-dichloro-2-methoxyacridine and 4-(pyrrolidin-1-yl)butan-1-amine (Step 3), the title compound was obtained; MS (Found M+1=384). | COc1ccc2nc3cc(Cl)ccc3c(NCCCCN3CCCC3)c2c1 | null | null | null |
1,621,526 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:11][CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[K+].[K+]>O>[C:1]1([C@H:7]([NH:9][CH2:11][CH2:12][CH2:13][OH:14])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | C[C@@H](N)c1ccccc1 | OCCCCl | null | O=C([O-])[O-] | [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 | 100 | 5 | To a solution of (R)-1-phenylethanamine (364 g, 3.00 mol) in water (43.7 ml) was added 3-chloropropan-1-ol (142 g, 1.50 mol) at room temperature. The mixture was stirred at 100° C. for 5 hours. The resulting mixture was cooled to 0° C. and basified with saturated aqueous potassium carbonate. The organic layer was extra... | C[C@@H](NCCCO)c1ccccc1 | null | 83.3 | null |
1,481,043 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C([O:9][C@@H:10]1[C@@H:15]([O:16]C(=O)C2C=CC=CC=2)[C@H:14]([O:25]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:34][O:35]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[O:44][C@@H:45]1[C@@H:50]([CH2:51][O:52]C(=O)C2C=CC=CC=2)[O:49][C@H:48]([O:61][C@@H:62]2[C@@H:100]([CH2:101][O:102]C(=O)C3C=CC=CC=3)[O:99][C@@H:65]([O:66][NH:67][C:68](=[O:98])[CH2:... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CC(OCC(=O)NO[C@@H]5O[C@H](COC(=O)c6ccccc6)[C@@H](O[C@H]6O[C@H](COC(=O)c7ccccc7)[C@@H](O[C@H]7O[C@H](COC(=O)c8ccccc8)[C@@H](OC(=O)c8ccccc8)[C@H](OC(=O)c8ccccc8)[C@H]7OC(=O)c7ccccc7)[C@H](OC(=O)c7ccccc7)[C@H]6OC(=O)c6ccccc6)[C@H](OC(=O)c6ccccc6)[C@H]5OC(=O)c5ccccc5)CC[C@]4(C)[C@H... | null | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 24 | Amide 132 (345 mg, 175 μmol) was dissolved in MeOH/THF 1:1 (16 mL). NaOMe (500 μL of a 6M solution) was added and the solution was stirred at room temperature for 24 hrs. The mixture was neutralized with acidic resin and the solution filtered before the solvent was evaporated to yield the white solid product which was ... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CC(OCC(=O)NO[C@@H]5O[C@H](CO)[C@@H](O[C@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@]12C | null | 74.7 | null |
1,057,651 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [Cl-].[C:2]([CH:4]1[CH2:9][CH2:8][NH2+:7][CH2:6][CH2:5]1)#[N:3].C(N(CC)CC)C.[CH2:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18]>ClCCl>[CH2:17]([S:19]([N:7]1[CH2:8][CH2:9][CH:4]([C:2]#[N:3])[CH2:5][CH2:6]1)(=[O:21])=[O:20])[CH3:18] | N#CC1CC[NH2+]CC1 | CCS(=O)(=O)Cl | 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 | 1 | In a dry round bottom flask was placed 4-cyanopiperidinium chloride (13, 5 g, 45.4 mmol) dichloromethane (150 ml) and triethylamine (18.98 ml, 136 mmol). To the reaction was added dropwise ethanesulfonyl chloride (4.56 ml, 45.4 mmol) and the solution stirred 1 hour and quenched with water (100 ml). The mixture was extr... | CCS(=O)(=O)N1CCC(C#N)CC1 | null | null | null |
898,103 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [OH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH:12]([CH3:14])[CH3:13])[N:3]=1.[Br:15]N1C(=O)CCC1=O>ClCCl>[Br:15][C:5]1[N:4]([CH:12]([CH3:13])[CH3:14])[N:3]=[C:2]([OH:1])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8] | CCOC(=O)c1cn(C(C)C)nc1O | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 6 | Ethyl 3-hydroxy-1-isopropylpyrazole-4-carboxylate (10.5 g) was dissolved in dichloromethane (100 mL) and to the stirred solution was added N-bromosuccinimide (14.1 g) under ice cooling. The reaction mixture was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure and the obtained resi... | CCOC(=O)c1c(O)nn(C(C)C)c1Br | null | 40.2 | null |
1,101,206 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]([O:17]CC)=[O:16])[C:9]2=[O:20])=[CH:4][CH:3]=1.[OH-].[Li+]>C(O)C.O>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][CH2:11][N:... | CCOC(=O)CN1CCCC(c2ccc(F)cc2)(c2ccc(F)cc2)C1=O | null | null | [Li+] | [OH-] | 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 | 80 | null | The product from Example 90C (0.40 g, 1.07 mmol) was dissolved in ethanol (20 mL). A solution of lithium hydroxide (0.21 g, 8.57 mmol) in water (5 mL) was added and the reaction was heated to 80° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated, neutralized with 2 N HCl, and then dilute... | O=C(O)CN1CCCC(c2ccc(F)cc2)(c2ccc(F)cc2)C1=O | null | null | null |
31,022 | ord_dataset-56c07ce5503b46d1805bdf471f8f1c55 | null | 1977-01-01T00:10:00 | true | Cl[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[C:13]1[N:14]([CH3:21])[C:15]([N+:18]([O-:20])=[O:19])=[CH:16][N:17]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>O1CCOCC1>[O:25]1[CH2:26][CH2:27][N:22]([CH2:2][CH2:3][N:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:6]=[C:5]2[C:13]2[N:14... | Cn1c([N+](=O)[O-])cnc1-c1nc2ccccc2n1CCCl | C1COCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | 0.31 g. of 1-(2-chloroethyl)-2-(5-nitro-1-methyl-2-imidazolyl)-benzimidazole are boiled for 12 hours with 0.18 g. of morpholine in 50 ml. of dioxane. By evaporation and preparative thin-layer chromatography of the mixture, 50 mg. of 1-(2-morpholinoethyl)-2-(5-nitro-1-methyl-2-imidazolyl)-benzimidazole is obtained, the ... | Cn1c([N+](=O)[O-])cnc1-c1nc2ccccc2n1CCN1CCOCC1 | null | null | null |
666,256 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | C([O:5][C:6](=[O:40])[CH2:7][CH:8]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[O:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])(=[O:14])=[O:13])[CH:9]=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:39][N:37]([CH... | CN(C)CCOc1ccc2ccccc2c1CCOc1ccccc1S(=O)(=O)NC(C=O)CC(=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 | null | 3-(2-{2-[2-(2-Dimethylamino-ethoxy)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-4-oxo-butyric acid tert-butyl ester (190 mg, 0.33 mmol) was stirred with trifluoroacetic acid (0.4 mL) in CH2Cl2 (1.2 mL) at room temperature for 1 h. Analytical HPLC analysis indicated the reaction was complete. The reaction mixture was... | CN(C)CCOc1ccc2ccccc2c1CCOc1ccccc1S(=O)(=O)NC(C=O)CC(=O)O | null | 18.2 | null |
1,135,272 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [CH3:1][C:2]1([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C@@H:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C@H:17]4[NH:16][C:15]3=[O:23])[CH2:10][CH2:9]2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:24]1([C:27](O)=[O:28])[CH2:26][CH2:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:24]1([C:27]([... | CC1(N2CCC(N3C(=O)N[C@@H]4CCCC[C@H]43)CC2)CCNCC1 | O=C(O)C1CC1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1 | To the solution (3aR,7aR)-1-[1-(4-methyl-4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one (HCl salt, 99 mg, 0.25 mmol) in dry DMF (3 mL) was added cyclopropanecarboxylic acid (26 mg, 0.3 mmol) followed by HATU (114 mg, 0.3 mmol) and diisopropylethylamine (0.10 mL, 0.5 mmol) and the mixture was s... | CC1(N2CCC(N3C(=O)N[C@@H]4CCCC[C@H]43)CC2)CCN(C(=O)C2CC2)CC1 | null | 27.8 | null |
464,826 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | [CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=2)[CH:12]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([Cu])#[N:26].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:25]#[N:26])=[CH:16][CH:17]=2)[CH:12]=[C:11]([C:20]([O:22][CH2:23]... | N#C[Cu] | CCOC(=O)c1cc(OCc2ccccc2)c2ccc(Br)cc2c1 | null | null | null | 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 | null | A solution of 12 (9.46 g, 27.2 mmol) in anhydrous DMF (12.6 mL) under Ar was treated with CuCN (2.92 g, 32.6 mmol, 1.2 equiv) and the mixture was warmed at reflux for 20 h. The reaction mixture was cooled to 25° C. and poured into 250 mL of H2O to which FeCl3 (5.29 g, 32.6 mmol, 1.2 equiv) was added with swirling. The ... | CCOC(=O)c1cc(OCc2ccccc2)c2ccc(C#N)cc2c1 | null | 74.3 | null |
1,752,293 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH2:1]([NH:8][C:9]1[C:10]2[N:11]([CH:29]=[CH:30][C:31]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:12]([C:15]2[CH:16]=[C:17]([S:21]([NH:24]C(C)(C)C)(=[O:23])=[O:22])[CH:18]=[N:19][CH:20]=2)=[N:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[CH2:1]([NH:8][C:9]1[C:10]2[N:11]([CH:29]=[CH:30]... | CC(C)(C)NS(=O)(=O)c1cncc(-c2nnc(NCc3ccccc3)c3c(-c4ccccc4)ccn23)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 50 | 1 | 5-(1-(Benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)-N-(tert-butyl)pyridine-3-sulfonamide (0.150 g, 0.293 mmol) was dissolved in TFA (10 mL) and stirred at 50° C. for 1 h. TFA was removed under reduced pressure and the resulting residue was diluted with saturated sodium bicarbonate (100 mL). The aqueous mixtur... | NS(=O)(=O)c1cncc(-c2nnc(NCc3ccccc3)c3c(-c4ccccc4)ccn23)c1 | null | 44.9 | null |
239,685 | ord_dataset-960c6b9c4fc74afd90a3ebf713215626 | null | 1991-01-01T00:12:00 | true | [F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](=[O:13])[CH2:7][CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:13])[CH2:7][CH:8]2[CH2:12][CH2:11][N:10]([CH2:17][CH2:18][OH:19])[CH2:9]2)=[CH:14][CH:15]=1 | O=C(CC1CCNC1)c1ccc(F)cc1 | OCCBr | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 30.5 g of 3-(4-fluorophenacyl)pyrrolidine (Chem. Pharm. Bull., 1977, 25(8), p. 1911-1922), 19.4 g of 2-bromoethanol, 15.6 g of sodium carbonate and 400 ml of acetonitrile is heated to reflux for 6 hours. The mixture is concentrated, the residue is taken up in 150 ml of aqueous saline, the product is extrac... | O=C(CC1CCN(CCO)C1)c1ccc(F)cc1 | null | null | null |
1,548,605 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[N:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[NH:14][C:13](=[O:20])[CH2:12]2>>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:14]2[CH:15]3[CH2:18][CH2:19][N:11]([CH2:17][CH2:16]3)[CH2:12][C:13]2=[O:20])=[CH:3][CH:4]=1)([O-:10])=[O:9] | O=[N+]([O-])c1ccc(Br)cn1 | O=C1CN2CCC(CC2)N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following general N—C coupling procedure 1, 5-bromo-2-nitropyridine and 1,4-diazabicyclo[3.2.2]nonan-3-one were combined and gave 4-(6-nitropyridin-3-yl)-1,4-diazabicyclo[3.2.2]nonan-3-one (418 mg) in 64% yield. | O=C1CN2CCC(CC2)N1c1ccc([N+](=O)[O-])nc1 | null | 64 | null |
463,647 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:5][C:4]=1[CH:22]=[N:23][O:24][CH2:25][CH3:26]>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:17])[F:18])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:5... | CCON=Cc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)ccc1Cl | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 4 | Borane-pyridine complex (3 ml) and 10-percent hydrochloric acid (30 ml) were added dropwise in succession at 0° C. to a solution of 3-(4-chloro-3-ethoxyiminomethylphenyl)-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (3.8 g) in 40 ml of ethanol. In the course of 16 hours, another 12 ml of boranepyri... | CCONCc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)ccc1Cl | null | null | null |
1,262,416 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7](Cl)=[N:8][OH:9].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH3:21])[CH:15]=1)#[CH:13].N>>[Cl:1][C:2]1[CH:11]=[C:6]([C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH3:21])[CH:15]=3)[O:9][N:8]=2)[CH:5]=[N:4][CH:3]=1 | ON=C(Cl)c1cncc(Cl)c1 | C#Cc1ccc(F)c(C)c1 | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The titled compound was prepared according to Method CB using the product of Example 69B (57 mg, 0.3 mmol) and 4-ethynyl-1-fluoro-2-methylbenzene (Aldrich, 40 mg, 0.3 mmol). 1H NMR (300 MHz, DMSO-d6) δ2.34 (d, J=2.0 Hz, 3H), 7.38 (t, J=9.2 Hz, 1H), 7.72 (s, 1H), 7.74-7.81 (m, 1H), 7.84-7.91 (m, 1H), 8.42 (t, J=2.1 Hz, ... | Cc1cc(-c2cc(-c3cncc(Cl)c3)no2)ccc1F | null | null | null |
1,458,350 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[C:11]([NH2:13])[NH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:14]NN>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[C:11]([NH2:13])[N:10]([CH3:14])[N:9]=2)[CH:5]=[CH:4][N:3]=1 | CNN | Nc1cc(-c2ccnc(Cl)c2)n[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This title intermediate was prepared starting from 18.B (3.10 g, 17.3 mmol) according the procedure described above for conversion of 18.B to 18.C, except that methylhydrazine (3.5 equiv.) was used. The crude product was purified by flash chromatography on silica gel using 0-8% MeOH/CH2Cl2 for elution to provide 23.A (... | Cn1nc(-c2ccnc(Cl)c2)cc1N | null | 89 | null |
1,389,782 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]2[C:13](=[O:19])[NH:14][C:15](=[S:18])[NH:16][CH:17]=2)=[CH:3]1.[Cl:20][C:21]1[CH:37]=[CH:36][C:24]([O:25][C:26]2[CH:33]=[CH:32][C:31]([CH2:34]Cl)=[CH:30][C:27]=2[C:28]#[N:29])=[CH:23][C:22]=1[C:38]([F:41])([F:40])[F:39].CCN(C(C)C)C(C)C>C(Cl)(Cl... | Cn1cc(Cc2c[nH]c(=S)[nH]c2=O)c2ccccc21 | N#Cc1cc(CCl)ccc1Oc1ccc(Cl)c(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | The same procedure as E80 from 5-[(1-methyl-1H-indol-3-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (50 mg, 0.184 mmol), 2-(4-chloro-3-(trifluoromethyl)phenoxy)-5-(chloromethyl)benzonitrile (77 mg, 0.221 mmol) and DIPEA (0.097 mL, 0.553 mmol) in chloroform (2 mL) was added to afford the title compound (76 mg, 71.... | Cn1cc(Cc2c[nH]c(SCc3ccc(Oc4ccc(Cl)c(C(F)(F)F)c4)c(C#N)c3)nc2=O)c2ccccc21 | null | 71.1 | null |
1,763,234 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:34]#[N:35])=[C:13]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][N:18]([CH:23]([CH2:31][CH3:32])[C:24]([O:26]C(C)(C)C)=[O:25])[C:17](=[O:33])[CH:16]=2)[CH:14]=1>ClCCl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:34]#[N:35])=[C:13]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][N:18]([CH:23]([... | CCC(C(=O)OC(C)(C)C)n1cc(OC)c(-c2cc(Cl)ccc2C#N)cc1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | Under argon and at RT, 7.8 ml (101.8 mmol, 10 eq.) of trifluoroacetic acid were added to a solution of 4.1 g (10.2 mmol) of tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoate (racemate) in 40 ml of dichloromethane, the mixture was stirred at RT for 1 h, a further 7.8 ml (101.8 mmol, 10 e... | CCC(C(=O)O)n1cc(OC)c(-c2cc(Cl)ccc2C#N)cc1=O | null | null | null |
1,343,308 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[C:22]3[N:21]=[CH:20][C:19](=[O:23])[NH:18][C:17]=3[N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:24]([C:28]1[CH:32]=[C:31]([N:33]=[C:34]=[O:35])[N:30]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:29]=1)([CH3:27])([CH3:26])[CH3:25]>>[C:24]([C:2... | Nc1ccc(Oc2ccnc3[nH]c(=O)cnc23)c2ccccc12 | CC(C)(C)c1cc(N=C=O)n(-c2ccccc2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Method F2 was used with 8-(4-aminonaphthalen-1-yloxy)pyrido[2,3-b]pyrazin-3(4H)-one and 3-tert-butyl-5-isocyanato-1-phenyl-1H-pyrazole to afford the title compound as a slightly yellow solid (65 mg, 80%). | CC(C)(C)c1cc(NC(=O)Nc2ccc(Oc3ccnc4[nH]c(=O)cnc34)c3ccccc23)n(-c2ccccc2)n1 | null | null | null |
973,075 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Cl[C:11]1[C:20]2[C:15](=[C:16]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][C:13](=[O:29])[CH:12]=1>>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:11]1[C:20]2[C:15](=[C:16]([O:23][CH:24]3[CH2:2... | Cc1cccc(Cl)c1N | COc1ccc2c(Cl)cc(=O)oc2c1OC1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-chloro-6-methylaniline and 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one following the procedure outlined in Example 16. 1H NMR (400 MHz, DMSO-d6): δ 9.18 (s, 1H), 7.94 (d, 1H), 7.50 (dd, 1H), 7.42-7.34 (m, 2H), 7.16 (d, 1H), 4.82 (m, 1H), 4.28 (s, 1H), 3.90 (s, 3H), 2.21... | COc1ccc2c(Nc3c(C)cccc3Cl)cc(=O)oc2c1OC1CCCC1 | null | null | null |
674,510 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1(OCC1C=CC=CC=1)[CH2:13][O:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=[O:26])C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:26])[CH2:10][CH:9]1[CH2:13][O:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2] | CCOC(C)=O | COCC1(OCc2ccccc2)CCCN1C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 12 | The benzyloxy-2-methoxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester (217.00 mg, 0.68 mmol) was taken up in ethyl acetate in a Paar vessel. The solution was flushed with argon and Pd/C (100 mg) was added to the vessel. The argon atmosphere was replaced by hydrogen at 50 psi. The vessel was shaken for 12 h. The hyd... | COCC1CC(O)CN1C(=O)OC(C)(C)C | null | null | null |
1,397,272 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | Br[C:2]1[C:7]2[N:8]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[C:9]([C@@H:11]([NH:13][C:14]3[N:22]=[CH:21][N:20]=[C:19]4[C:15]=3[N:16]=[CH:17][N:18]4[CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][C:3]=1[F:35].[CH:36]1(B(O)O)[CH2:38][CH2:37]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1... | C[C@H](Nc1ncnc2c1ncn2C1CCCCO1)c1nc2ccc(F)c(Br)c2n1-c1ccccn1 | OB(O)C1CC1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | To a solution of [(S)-1-(7-bromo-6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine (267 mg, 0.49 mmol) in dioxane (10 mL) and water (0.5 mL) was added cyclopropylboronic acid (64 mg, 0.75 mmol), cesium carbonate (242 mg, 0.75 mmol) and tetrakis(triphenylphosphine)pallad... | C[C@H](Nc1ncnc2c1ncn2C1CCCCO1)c1nc2ccc(F)c(C3CC3)c2n1-c1ccccn1 | null | 24.2 | null |
637,957 | ord_dataset-a192df1b44174b5886ef2005f759d553 | null | 2004-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]2[O:8][CH2:9][O:10][C:5]2=[CH:4][C:3]=1[C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17]([O:21][CH3:22])=[CH:18]2)=[CH:13][CH:12]=1.Cl.[N:24]([O-])=O.[Na+].O>C(O)(=O)C>[CH3:22][O:21][C:17]1[CH:16]=[CH:15][C:14]2=[CH:13][CH:12]=[C:11]3[C:20]([N:24]=[N:1][C:2]4[CH:7]=[C:6]5[O:8][CH2:9][O:10][C:5... | COc1ccc2ccc(-c3cc4c(cc3N)OCO4)cc2c1 | O=N[O-] | null | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 8 | 7-(2-Amino-4,5-methylenedioxyphenyl)-2-methoxynaphthalene 49 (70 mg, 0.24 mmol) was dissolved in acetic acid (2.0 mL) and concentrated hydrochloric acid (0.4 mL). The solution was cooled in an ice bath and diazotized by the dropwise addition of a solution of sodium nitrite (0.16 g in 1.6 mL water). The resulting diazon... | COc1ccc2ccc3c4cc5c(cc4nnc3c2c1)OCO5 | null | 82.2 | null |
624,417 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:17]1([CH:7]([C:1]2[CH:2]=[CH... | c1ccc(C(CCN2CCCNCC2)c2ccccc2)cc1 | ClCc1ccc2ccccc2n1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 70 | 14 | The resulting 1-(3,3-diphenylpropyl)homopiperazine was dissolved in 3 mL of ethanol, mixed with 228 mg of 2-(chloromethyl)quinoline hydrochloride and 141 mg of potassium carbonate, and stirred at 70° C. for 14 hours. The mixture was cooled to room temperature and the ethanol was removed under reduced pressure, 20 mL of... | c1ccc(C(CCN2CCCN(Cc3ccc4ccccc4n3)CC2)c2ccccc2)cc1 | null | null | null |
834,621 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [ClH:1].[CH2:2]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]>CO.[Pd]>[ClH:1].[CH2:2]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]2[... | CCCCN1CC=C(c2ccccc2C2CC(C)(C)CC(C)(C)C2)CC1 | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 1-butyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-1,2,3,6-tetrahydropyridine hydrochloride (48 mg, 0.12 mmol) produced in Example (102f) in methanol (3 mL) was added 10% palladium on carbon (100 mg, wet), followed by stirring for 4 hours at room temperature and atmospheric pressure under a hydrogen a... | CCCCN1CCC(c2ccccc2C2CC(C)(C)CC(C)(C)C2)CC1 | null | 19.1 | null |
486,915 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | FC(F)(F)C(O)=O.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([NH:25][CH2:26][CH2:27][N:28]1[C@@H:33]([CH3:34])[CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][C@H:29]1[CH3:42])=[O:24]>ClCCl>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H](C)N1CCNC(=O)[C@@H]1CCCCN1c1nc2ccccc2o1 | 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 | 1.5 | Trifluoroacetic acid (10 ml) was added to a solution of tert-butyl (cis)-4-[2-([(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinyl]carbonylamino)ethyl]-3,5-dimethyl-1-piperazinecarboxylate (0.95 g) [see Preparation 8] in dichloromethane (10 ml) at 0° C. The reaction mixture was then stirred at room temperature for 1.5 hours, a... | C[C@@H]1CNC[C@H](C)N1CCNC(=O)[C@@H]1CCCCN1c1nc2ccccc2o1 | null | 86.2 | null |
802,080 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [CH:1]([C:3]1[C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=1)=[O:2].[BH4-].[Na+]>C1COCC1.C(O)C>[OH:2][CH2:1][C:3]1[C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=[C:5]([C:17]2[CH:18]=[CH:19][... | CC(C)(C)OC(=O)Nc1ccc(-c2ccccc2)nc1C=O | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCO | null | null | null | null | null | null | null | null | null | 0 | 0.17 | To a solution of 1E (2.37 g, 7.94 mmol) in THF (10 mL) and ethanol (20 mL) at 0° C. was added sodium borohydride (300 mg, 7.94 mmol) in several portions. After addition, the reaction was stirred at 0° C. for 10 min, and no starting material was detected by LC-MS. The resultant mixture was quenched with saturated aqueou... | CC(C)(C)OC(=O)Nc1ccc(-c2ccccc2)nc1CO | null | 94.3 | null |
978,616 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.[CH2:13]1[CH:22]2[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15][NH:14]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:14]1[CH2:15][CH2:16][CH:17]3[CH:22]([CH2:21][CH2:20][CH2:19][CH2:18... | Clc1nncc2cc(Br)ccc12 | C1CCC2CNCCC2C1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 180 | null | A mixture of 6-bromo-1-chlorophthalazine (Example 1, 0.1 g, 411 μmol), decahydroisoquinoline (114 mg, 821 μmol), potassium carbonate (57 mg, 411 μmol) and 5 mL acetonitrile was added to a glass microwave reaction vessel. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Che... | Brc1ccc2c(N3CCC4CCCCC4C3)nncc2c1 | null | 105.4 | null |
1,555,734 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10](=[O:12])[N:17]1[CH2:22][CH2:21][NH:20][CH2... | C1CNCCN1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O | 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 | 25 | 8 | To 1.00 g (4.33 mmol) of (S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanoic acid was added 750 mg (8.66 mmol) of piperazine, 20 mL of DCM, 1.34 g (6.5 mmol) of DCC and 17.9 mL (12.99 mmol) of TEA. This was allowed to stir overnight at room temperature. The next morning, it was diluted with more DCM, and filtered. The... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCNCC1 | null | 79 | null |
199,853 | ord_dataset-aa9e93ade540499c920a9c3b18e8edaa | null | 1989-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][C:4]=1[OH:11].[H-].[Na+].FC(F)(F)S(O[CH2:20][C:21]([F:24])([F:23])[F:22])(=O)=O.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:11][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:9]=[O:10] | COc1cc(C=O)ccc1O | O=S(=O)(OCC(F)(F)F)C(F)(F)F | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0.5 | To a solution of 3.96 g of vaniline (e-1) (26.0 mmol) in 26 ml of dry DMF was added 1.04 g of 60% NaH (26.0 mmol) slowly, and the mixture was stirred for 30 min. in a stream of nitrogen. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (6.64 g: 28.6 mmol) was added dropwise to the mixture and stirred overnight at room te... | COc1cc(C=O)ccc1OCC(F)(F)F | null | 98.2 | null |
652,327 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23]CC=C)=[O:22])[CH:16]=1)[C:10]#[N:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2... | C=CCOC(=O)c1cccc(COC[C@H](C#N)NC(=O)OC(C)(C)C)c1 | null | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCN1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of (S)-2-t-butoxycarbonylamino-3-(3-allyloxycarbonylbenzyloxy)-propionitrile (8.0 g, 22.22 mmol) in THF (100 mL) is added morpholine (19.4 mL, 222 mmol). After deoxygenation with bubbling nitrogen (2 min.), Pd(PPh3)4 (1.28 g, 1.11 mmol) is added in one portion, and the solution is stirred 1 h. Solvent is ... | CC(C)(C)OC(=O)N[C@@H](C#N)COCc1cccc(C(=O)O)c1 | null | null | null |
71,160 | ord_dataset-520610070b3c4780a03b44c7fcecc28f | null | 1980-01-01T00:10:00 | true | [N:1]([O-:3])=[O:2].[Na+].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:15][C:14](=[CH:16][N+:17]([O-])=[O:18])[CH2:13][N:12]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:10]=2[CH:27]=1>C(O)(=O)C.O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:15]=[C:14]([C:16]([N+:1]([O-:3])=[O:2])=[N:17][OH:18])[CH2:13][N:12]=[C:11]([C:20]... | O=N[O-] | O=[N+]([O-])C=C1CN=C(c2ccccc2F)c2cc(Cl)ccc2N1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | Sodium nitrite, 5 g (0.072 mole), was added in portions over a period of 5 min to a solution of 20 g (0.06 mole) of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2-nitromethylene-2H-1,4-benzodiazepine* in 100 ml of glacial acetic acid. Following the addition, the reaction mixture was stirred at room temperature for 15 min. T... | O=[N+]([O-])C(=NO)C1=Nc2ccc(Cl)cc2C(c2ccccc2F)=NC1 | null | null | null |
1,451,207 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][O:31][CH3:32].C(OCC)(=O)C>CN(C=O)C>[CH3:32][O:31][CH2:30][CH2:29][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][... | CC(C)(C)OC(=O)NCCc1nc(-c2ccccc2)c[nH]1 | COCCBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A suspension of tert-butyl 2-(4-phenyl-1H-imidazol-2-yl)ethylcarbamate (400 mg, 1.39 mmol, prepared according to example 7, steps 1-2) and potassium carbonate (423 mg, 3.06 mmol) in DMF (4 mL) was stirred for 30 min at RT. After cooling to 0-5° C., 1-bromo-2-methoxyethane (157 μL, 1.67 mmol) was added. The ice bath was... | COCCn1cc(-c2ccccc2)nc1CCNC(=O)OC(C)(C)C | null | null | null |
79,753 | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | null | 1981-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](Cl)([Cl:10])[Cl:9])[N:3]=1.Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([Cl:10])[Cl:9])[N:3]=1 | Clc1cccc(C(Cl)(Cl)Cl)n1 | 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 | null | A mixture of 23.1 g (0.10 mole) of 2-chloro-6-(trichloromethyl)pyridine, 10.0 g of methanol, 15.0 g of concentrated hydrochloric acid and 40.0 g (0.20 mole) of ferrous chloride as the tetrahydrate was stirred while heating to reflux. The mixture was a slurry which slowly became fluid and a two-phase liquid mixture resu... | Clc1cccc(C(Cl)Cl)n1 | null | null | null |
1,368,798 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | Br[C:2]1[CH:3]=[C:4]([C:10]([Br:13])=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[N:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Br:13][C:10]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]([C:17]2[CH:18]=[N:19][CH:20]=[C:15]([CH3:14])[CH:16]=2)=[N:12][CH:11]... | Cc1cncc(B(O)O)c1 | CCOC(=O)c1cc(Br)ncc1Br | 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 | 50 | 8 | To a solution ethyl 2,5-dibromoisonicotinate (1-2, 1.5 g, 4.86 mmol) in degassed dimethylformamide (24 mL) at 25° C. was added (5-methylpyridin-3-yl)boronic acid (0.665 g, 4.86 mmol), PdCl2dppf (0.355 g, 0.486 mmol), cesium carbonate (4.75 g, 14.6 mmol) and water (0.262 mL, 14.57 mmol). The reaction flask was purged wi... | CCOC(=O)c1cc(-c2cncc(C)c2)ncc1Br | null | null | null |
190,565 | ord_dataset-be83cbc722064f3696975001242f9f1a | null | 1989-01-01T00:05:00 | true | [CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([C:15](=[O:18])[CH2:16][Cl:17])[CH:11]=[CH:10][C:9]=2[OH:19])=[O:5])[CH3:2].[CH2:20]([NH2:23])[CH:21]=[CH2:22].Cl>CS(C)=O>[ClH:17].[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([C:15](=[O:18])[CH2:16][NH:23][CH2:20][CH:21]=[CH2:22])[CH:11]=[C... | C=CCN | CCOC(=O)c1cc2c(C(=O)CCl)ccc(O)c2[nH]1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 2.8 g of 4-chloroacetyl-7-hydroxyindole-2-carboxylic acid ethyl ester is combined with 1.5 ml of allylamine and 15 ml of absolute dimethyl sulfoxide and stirred at room temperature for one hour. Then 150 ml of 2N hydrochloric acid is added to the reaction mixture, the immediately formed precipitate is vacuum-filtered, ... | C=CCNCC(=O)c1ccc(O)c2[nH]c(C(=O)OCC)cc12 | null | null | null |
226,562 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | [OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].[Br:25][CH2:26][CH2:27][CH2:28]Br>CC(CC)=O>[Br:25][CH2:26][CH2:27][CH2:28][O:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=... | BrCCCBr | O=C(c1ccccc1)c1ccc(O)c([N+](=O)[O-])c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | null | 4-hydroxy-3-nitrobenzophenone (2.5 g) and 7.1 g of potassium carbonate were suspended in 15 ml methylethylketone. The suspension was stirred under heating with reflux for 30 minutes, added with 1,3-dibromopropane and then heated with reflux for 6 hours. The reaction mixture was cooled down to room temperature, and inso... | O=C(c1ccccc1)c1ccc(OCCCBr)c([N+](=O)[O-])c1 | null | null | null |
1,060,929 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[N:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O.[CH2:19]([O:21][NH2:22])[CH3:20]>>[CH2:19]([O:21][NH:22][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][N:17]=[CH:18][C:10]=1[NH:9][C:3]1[CH:2]=[CH:7][C:6]([I:8])=[CH:5][CH:4]=1)[CH3:20] | CCON | O=C(O)c1ccncc1Nc1ccc(I)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 | N-ethoxy-3-(4-iodo-phenylamino)-isonicotinamide was synthesized according to the procedure for General Method 1, outlined above, starting with 0.30 mmol of 3-[(2-chloro-4-iodophenyl)amino]isonicotinic acid (intermediate 2) and 0.40 mmol of O-ethyl-hydroxylamine LC/MS [9.14 min; 418 (M+1)] | CCONC(=O)c1ccncc1Nc1ccc(I)cc1 | null | null | null |
21,338 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | FC1C=CC(C(O)C=CC[N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[O:27])[CH2:14][CH2:13]2)=CC=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[O:27]=[C:19]1[N:18]([CH:15]2[CH2:14][CH2:13][NH:12][CH2:17][CH2:16]2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20]1 | O=c1[nH]c2ccccc2n1C1CCN(CC=CC(O)c2ccc(F)cc2)CC1 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 1.5 | A mixture of 1-[4-(p-fluorophenyl)-4-hydroxy-2-butenyl]-4-(2-keto-1-benzimidazolinyl)piperidine (0.56 g) in chloroform (12 ml) and manganese dioxide (4.4 g) was stirred for 1.5 hours under ice-cooling. Filtration of inorganic materials and concentration of the filtrate afforded 1-[4-fluorophenyl)-4-oxo-2-butenyl]-4-(2-... | O=c1[nH]c2ccccc2n1C1CCNCC1 | null | null | null |
157,852 | ord_dataset-58ec6779628e43e2b3f0972725f262e6 | null | 1987-01-01T00:05:00 | true | [O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:18])=[O:7].ClS([N:23]=[C:24]=[O:25])(=O)=O.C(#N)C>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[N:10]([C:24]([NH2:23])=[O:25])[C:9]1=[O:18])=[O:7] | O=C1Nc2cc(F)ccc2C1C(=O)c1ccco1 | O=C=NS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | null | null | Following substantially the procedure of Example 19, the title was prepared in 17% yield from: 3-(2-furoyl)-6-fluoro-2-oxindole (0.30 g, 1.2 mmole), chlorosulfonyl isocyanate (0.20 g, 1.4 mmole), acetonitrile (15 ml), and water (10 ml), Yield=0,060 g; m.p.=231°-235° C. | NC(=O)N1C(=O)C(C(=O)c2ccco2)c2ccc(F)cc21 | null | 17 | null |
227,856 | ord_dataset-d98d003e9abb4b579746c5a361466e14 | null | 1991-01-01T00:05:00 | true | [CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16](=[NH:20])[O:17][CH2:18][CH3:19])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:21][O:22][CH2:23][C:24](Cl)=[O:25]>>[CH3:21][O:22][CH2:23][C:24]([N:20]=[C:16]([N:7]1[CH2:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15]... | CCOC(=N)N1Cc2ccccc2-c2ccccc2C1 | COCC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | starting from ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate and methoxyacetyl chloride, there is obtained ethyl N-(methoxyacetyl)-5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate as a syrup, mass spectrum m/e: 339 (1, M+H), 309 (1), 293 (98), 194 (20), 167 (100); | CCOC(=NC(=O)COC)N1Cc2ccccc2-c2ccccc2C1 | null | null | null |
266,424 | ord_dataset-a2ae447c4340438c8c3a827109aeb425 | null | 1993-01-01T00:04:00 | true | N(C(OC(C)(C)C)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:26]([NH:28][C@H:29]([C:42]([O:44][CH3:45])=[O:43])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:33][CH:32]=1)=[O:27])[C@@H:16]([CH3:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11... | CC(C)C[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](COCc1ccccc1)NC(=O)OC(C)(C)C)C(=O)NN | COC(=O)[C@H](Cc1ccc(OCC(=O)O)cc1)NC(=O)[C@@H](NC(=O)[C@H](COCc1ccccc1)NC(=O)OC(C)(C)C)[C@@H](C)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By using 2.50 g of Boc-Ser(Bzl)-Thr(Bzl)-Tyr(CH2COOH)-OCH3 and 2.23 g of Boc-Ser(Bzl)-Asn-Leu-NHNH2 and the same procedure as in Reference Example 7 was repeated to obtain 2.49 g (yield: 63.8%) of the above-mentioned objective product. | COC(=O)[C@H](Cc1ccc(OCC(=O)O)cc1)NC(=O)[C@@H](NC(=O)[C@H](COCc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](COCc1ccccc1)NC(=O)OC(C)(C)C)[C@@H](C)OCc1ccccc1 | null | 63.8 | null |
1,394,338 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[O:19][C:18](=[O:21])[C:17]([C:22]([OH:24])=O)=[CH:16]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:49]1([S:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]2[CH:69]=[CH:68][CH:67]=[C:66]([NH2:70])[CH:65]=2)(=[O:57])=[O:56])[CH2:54]... | Nc1cccc(-c2ccccc2S(=O)(=O)N2CCOCC2)c1 | O=C(O)c1cc2cccc(O)c2oc1=O | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | null | DIEA (0.009 mL, 0.052 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.010 g, 0.047 mmol) and HATU (0.020 g, 0.052 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 2′-(Morpholine-4-sulfonyl)-biphenyl-3-ylamine (0.015 g, 0.047 mmol) was added and allowed... | O=C(Nc1cccc(-c2ccccc2S(=O)(=O)N2CCOCC2)c1)c1cc2cccc(O)c2oc1=O | null | 54.6 | null |
760,685 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]4[N:25]=[C:26]([CH2:29][CH2:30][NH2:31])[S:27][CH:28]=4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[CH:9][C:8]=1[Cl:32].[CH3:36][S:37]([CH2:40][C:41](O)=[O:42])(=[O:39])=[O:38].Cl.CN(... | NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 | CS(=O)(=O)CC(=O)O | null | CCN=C=NCCCN(C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | (4-(3-Fluorobenzyloxy)-3-chlorophenyl)-(6-(2-(2-aminoethyl)-thiazol-4-yl)-quinazolin-4-yl)-amine (0.229 mmol) was reacted with methanesulfonyl acetic acid (0.252 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.252 mmol) in DMF as outlined in procedure (I) to provide the title compound after pur... | CS(=O)(=O)CC(=O)NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 | null | null | null |
923,325 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.[OH:10][CH2:11][C:12]([NH:14][CH2:15][C@H:16]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[C:21]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([CH3:37])[CH:31]=1)=[N:22][CH:23]=[N:24]2)[CH3:17])=[O:13]>>[F:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C... | Fc1cccc(CCl)c1 | Cc1cc(Nc2ncnc3cccc(O[C@H](C)CNC(=O)CO)c23)ccc1O | null | null | null | null | null | null | null | 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 described in Example 3 was repeated using 1-(chloromethyl)-3-fluorobenzene and 2-hydroxy-N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]acetamide (obtained as described in Example 82, preparation of starting materials) to give the title compound as a light yellow solid in 25% yi... | Cc1cc(Nc2ncnc3cccc(O[C@H](C)CNC(=O)CO)c23)ccc1OCc1cccc(F)c1 | null | 25 | null |
470,446 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | Cl.Cl.[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([S:14]([N:17]([CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH2:18][C:19]([OH:21])=[O:20])(=[O:16])=[O:15])=[CH:11][CH:12]=2)[C:7]([NH:29][C:30]([NH2:32])=[NH:31])=[N:6][CH:5]=1.[H-].[Na+].[C:35](OC(=O)CN(S(C1C=C2C(C(Cl)=CN=C2Cl)=CC=1)(=O)=O)CC1C=NC=CC=1)([CH3:38])(... | CC(C)(C)OC(=O)CN(Cc1cccnc1)S(=O)(=O)c1ccc2c(Cl)cnc(Cl)c2c1 | N=C(N)Nc1ncc(Cl)c2ccc(S(=O)(=O)N(CC(=O)O)Cc3cccnc3)cc12 | null | Cl | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 60 | null | N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(3-pyridylmethyl)glycine dihydrochloride ##STR26## Guanidine hydrochloride (317 mg, 3.32 mmol was added in one portion to a stirred suspension of NaH (62.3 mg, 80% dispersion by wt in mineral oil, 2.08 mmol) in DME (10 mL) and the mixture was heated at 60° C. under ... | CC(C)(C)OC(=O)CN(Cc1cccnc1)S(=O)(=O)c1ccc2c(Cl)cnc(NC(=N)N)c2c1 | null | null | null |
719,609 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][S:33][CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39])=[CH:26][CH:25]=3)[C:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)([CH3:12])[CH2:8][S:9]2)=[CH:4][CH:3]=1... | O=S([O-])OO | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCSCCCC(F)(F)C(F)(F)F)cc1 | null | [K+] | null | 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 | 0 | 1 | (3RS,4RS)-7-Hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-{3-{4-[2-(4,4,5,5,5-pentafluoropentylthio)ethoxy]phenoxy}propyl}thiochroman (11) prepared in Step 8 (110 mg, 0.17 mmol) was dissolved in tetrahydrofuran (5 ml), which was then cooled down to 0° C. Oxone® (monopersulfate compound; DuPont product) (63 mg, 0.1 mmol) and w... | CC1(c2ccc(O)cc2)CSc2cc(O)ccc2C1CCCOc1ccc(OCCS(=O)CCCC(F)(F)C(F)(F)F)cc1 | null | 57 | null |
207,263 | ord_dataset-dd1de64954674e17b4b690cac09dc67b | null | 1990-01-01T00:04:00 | true | S(Cl)(Cl)=O.[Cl:5][C:6]1[C:15]([CH:16]=[N:17]O)=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:19][CH3:20])[CH:12]=2)[N:7]=1>CN(C)C=O>[Cl:5][C:6]1[C:15]([C:16]#[N:17])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:19][CH3:20])[CH:12]=2)[N:7]=1 | COc1ccc2nc(Cl)c(C=NO)cc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | 0 | 0.25 | Thionyl chloride (7.9 ml) was added dropwise over a 12 min period to a stirred solution of 16.3 g 2-chloro-6-methoxy-3-quinolinecarboxaldehyde oxime in 160 ml dimethylformamide at 0° C. The reaction mixture was stirred for 15 min longer at 0° C. and then at room temperature overnight. The mixture was then quenched in i... | COc1ccc2nc(Cl)c(C#N)cc2c1 | null | 98.3 | null |
674,966 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | C([O-])=O.[NH4+].[OH:5][CH:6]([CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)(=[O:11])=[O:10]>[Pd].C(O)C>[OH:5][CH:6]([CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:7][NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([NH2:... | O=[N+]([O-])c1ccc(S(=O)(=O)NCC(O)CN2CCCCC2)cc1 | null | null | [Pd] | O=C[O-] | [NH4+] | 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 | Ammonium formate (1.1 g, 17.46 mmol) followed by a slurry of 10% palladium on carbon catalyst (0.7 g) in ethanol was added in portions to a suspension of 4-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]nitrobenzene (Method 117; 1.2 g, 3.5 mmol) in ethanol (100 ml). The mixture was heated at reflux under nitrogen for 2 ho... | Nc1ccc(S(=O)(=O)NCC(O)CN2CCCCC2)cc1 | null | 84.8 | null |
1,159,334 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=O.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH:9]... | CC(C)(O)CNS(=O)(=O)c1ccc(C=O)cc1 | CC(=O)c1ccc(Cl)cc1Nc1ccccc1 | 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 | 8 | To a mixture of 1-(4-chloro-2-phenylaminophenyl)ethanone (0.401 g) and 4-formyl-N-(2-hydroxy-2-methylpropyl)-benzene sulfonamide (0.420 g) in MeOH (10 mL) was added NaOH (1.35 mL, 2 N, aq), and the mixture stirred overnight at RT. The product was concentrated under reduced pressure, washed with EtOAc, H2O and brine, th... | CC(C)(O)CNS(=O)(=O)c1ccc(C=CC(=O)c2ccc(Cl)cc2Nc2ccccc2)cc1 | null | 68.2 | null |
843,112 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:23]=[CH:22][N:21]([Si](C(C)C)(C(C)C)C(C)C)[CH:20]=4)[CH:18]=[C:13]3[C:12]([C:34]3[CH:38]=[CH:37][O:36][CH:35]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>CCO>[O:36]1[CH:37]=[CH:38][C:34]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([C:19]4[CH:23]=[CH:22]... | CC(C)[Si](C(C)C)(C(C)C)n1ccc(-c2cnc3c(c2)c(-c2ccoc2)cn3S(=O)(=O)c2ccccc2)c1 | null | null | O=C([O-])O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 110 | null | A mixture of 31 (15.3 mg, 0.28 μmol), EtOH (1.0 mL) and 10% aq. NaOH (0.5 mL) were heated at 110° C. for 40 min then cooled and poured onto saturated aqueous NaHCO3 (5 mL) and extracted with ethyl acetate (4×10 mL). The combined organic extracts were dried (MgSO4), concentrated and the residue purified by PTLC using 5%... | c1cc(-c2cnc3[nH]cc(-c4ccoc4)c3c2)c[nH]1 | null | 5,946 | null |
1,122,350 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH2:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[S:20]([CH2:23][CH2:24][NH2:25])(=[O:22])=[O:21])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]>>[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH2:26][C:27]2[S:28][CH:29]=[CH:30][N:31... | CC(C)N1CCC(N(Cc2nccs2)S(=O)(=O)CCN)CC1 | O=C(O)c1ccc(Cl)s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 5 iii) starting from 61 mg (1 equiv.) 5-chloro-thiophene-2-carboxylic acid and 129 mg (0.37 mmol) 2-amino-ethanesulfonic acid (1-isopropyl-piper... | CC(C)N1CCC(N(Cc2nccs2)S(=O)(=O)CCNC(=O)c2ccc(Cl)s2)CC1 | null | null | null |
1,722,674 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([NH2:7])=[O:6].[C:14](=O)([O-])[O-].[Cs+].[Cs+].S(OC)(OC)(=O)=O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([NH:7][CH3:14])=[O:6] | NC(=O)c1cc(F)cc([N+](=O)[O-])c1 | O=C([O-])[O-] | null | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | COS(=O)(=O)OC | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of 3-fluoro-5-nitrobenzamide (1.0 g, 5.43 mmoL) in DMF (17 mL) was added cesium carbonate (2.6 g, 8.14 mmoL) and dimethyl sulphate (547 mg, 4.34 mmol) and the reaction mixture was stirred at RT for 24 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 ml). The o... | CNC(=O)c1cc(F)cc([N+](=O)[O-])c1 | null | 74.3 | null |
1,704,368 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | C[C:2]1[C:3]([CH:13]2[CH2:16][N:15]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:14]2)=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[NH2:23][C:24]1[C:33]([C:34]([O:36][CH3:37])=[O:35])=[C:32]2[C:27]([CH:28]3[CH2:38][CH:29]3[CH2:30][O:31]2)=[CH:26][CH:25]=1>N1C=CC=CC=1.C(Cl)Cl>[F:8][C:7]1[CH:6]=[CH:5][C... | COC(=O)c1c(N)ccc2c1OCC1CC21 | Cc1c(F)ccc(S(=O)(=O)Cl)c1C1CN(C(=O)C(F)(F)F)C1 | 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 | null | 18 | A solution of methyl 4-fluoro-2-[1-(2,2,2-trifluoroacetyl)azetidin-3-yl]benzenesulfonyl chloride (Intermediate 89, 0.192 g) and methyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (Intermediate 42, 0.122 g) in pyridine (1 mL) and DCM (3 mL) was left to stand at room temperature for 18 ho... | COC(=O)c1c(NS(=O)(=O)c2ccc(F)cc2C2CN(C(=O)C(F)(F)F)C2)ccc2c1OCC1CC21 | null | 104.2 | null |
1,715,346 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH2:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:34]=[CH:33][C:23]([CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1>CN(C=O)C>[NH2:11][C:4]1[N:3]=[C:2]([Cl:1])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH2:19][C:2... | CCOP(=O)(Cc1ccc(CBr)cc1)OCC | Nc1nc(Cl)nc2[nH]cnc12 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 60 | null | To a solution of commercially available 2-chloro-9H-purin-6-amine (1 equiv.) in DMF (0.50 M) was added potassium carbonate (1.2 equiv.) and diethyl 4-(bromomethyl)benzylphosphonate (1 equiv.) (described in ref. 88, Ex 25 Step 1). The reaction mixture was then heated to 60° C. for 5 h. At this point the reaction mixture... | CCOP(=O)(Cc1ccc(Cn2cnc3c(N)nc(Cl)nc32)cc1)OCC | null | 18 | null |
193,802 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | [C:1]1([C:7]2([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][N:25]=[C:26]=[O:27]>C1C=CC=CC=1>[CH3:24][NH:25][C:26]([N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([O:13][C:14]2[CH:1... | CN=C=O | FC(F)(F)c1ccc(OC2(c3ccccc3)CCNCC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 4 | To a solution of 3.89 g of 4-phenyl-4-(4-trifluoromethylphenoxy)piperidine in 25 ml of benzene was added a solution of 0.68 g of methyl isocyanate in 25 ml of benzene. The reaction mixture was stirred for four hours at room temperaure. Evaporation of the volatiles afforded a solid which was purified by means of high pr... | CNC(=O)N1CCC(Oc2ccc(C(F)(F)F)cc2)(c2ccccc2)CC1 | null | 54.5 | null |
23,595 | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | null | 1977-01-01T00:05:00 | true | [I-].[K+].FC(F)(F)[C:5]1[CH:6]=[CH:7][C:8]2[N:14]3[C:15](CCl)=[N:16][N:17]=[C:13]3[CH2:12][N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:9]=2[CH:27]=1.C1(N)CC1>O1CCCC1>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:10]1[C:9]2[CH:27]=[CH:5][CH:6]=[CH:7][C:8]=2[N:14]2[CH:15]=[N:16][N:17]=[C... | FC(F)(F)c1ccc2c(c1)C(c1ccccc1Cl)=NCc1nnc(CCl)n1-2 | null | null | NC1CC1 | [I-] | [K+] | 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 | In the manner given in Example 1, potassium iodide and 8-(trifluoromethyl)-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine in tetrahydrofuran is treated with cyclopropylamine to give 8-trifluoromethyl-1-(cyclopropylamino)methyl]-6(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine. | Clc1ccccc1C1=NCc2nncn2-c2ccccc21 | null | null | null |
1,296,912 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N:13]3[C:17](=[O:18])[CH2:16][NH:15][C:14]3=[O:19])[CH:10]=[N:9]2)=[C:5]([CH3:20])[O:4][N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[CH2:25][CH2:26]Br>>[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[CH2:25][CH2:26][N:15]1[CH2:16][C:17](=[O:18])[N:... | Clc1cccc(CCBr)c1 | Cc1noc(C)c1Cn1cc(N2C(=O)CNC2=O)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared as in example 10-52 from 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione (example 10-1) and 3-chlorophenethyl bromide. Yield: 27%. MS M+H calculated 414.13; found 414.2. The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.20 μM. | Cc1noc(C)c1Cn1cc(N2C(=O)CN(CCc3cccc(Cl)c3)C2=O)cn1 | null | 27 | null |
1,471,522 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=[C:11]([C:19]([NH:21][C@@H:22]3[C@@H:27]([OH:28])[CH2:26][O:25][CH2:24][CH2:23]3)=[O:20])[CH:10]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:34]1[CH:39]=[N:38][CH:37]=[CH:36][N:35]=1)CCC>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=... | CCCC[Sn](CCCC)(CCCC)c1cnccn1 | O=C(N[C@H]1CCOC[C@@H]1O)c1cc(Cc2ccc(Cl)nc2)c2c(n1)CCCC2 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 1,5-anhydro-3-[({4-[(6-chloropyridin-3-yl)methyl]-5,6,7,8-tetrahydroquinolin-2-yl}carbonyl)amino]-2,3-dideoxy-L-threo-pentitol (Example 1, 0.038 g, 0.095 mmol) in 1 mL of dioxane under an atmosphere of nitrogen was added 2-(tributylstannyl)-pyrazine (0.060 mL g, 0.19 mmol) and tetrakis(triphenylphosphi... | O=C(N[C@H]1CCOC[C@@H]1O)c1cc(Cc2ccc(-c3cnccn3)nc2)c2c(n1)CCCC2 | null | null | null |
107,470 | ord_dataset-29d79fca4cec4a43b773d0ba25b27651 | null | 1983-01-01T00:08:00 | true | [H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.CC1C=CC(S(O[CH2:23][C@@H:24]([C@@H:39]2[C@:56]3([CH3:57])[C@H:42]([C@H:43]4[C@H:53]([CH2:54][CH2:55]3)[C@:51]3([CH3:52])[C:46]([CH2:47][C@@H:48]([O:65][CH:66]5[CH2:71][CH2:70][CH2:69][CH2:68][O:67]5)[CH2:49][C@@H:50]3[O:58][CH:59]3[CH2:64][CH2:63][CH2:62][CH2:61][O:60]3)=[CH:45]... | CCOC(C)OC(C)(C)C(F)(F)CC[C@@H](COS(=O)(=O)c1ccc(C)cc1)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC5CCCCO5)C[C@H](OC5CCCCO5)[C@]4(C)[C@H]3CC[C@]12C | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | 0 | 1 | A mixture of 0.410 g (0.0108 mol) of lithium aluminum hydride, 50 mL of tetrahydrofuran and 2.98 g (0.0033 mol) of [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-ol 21-(4-methylbenzenesulfonate) was heated at reflux (60°) for 1 hr and cooled to 0° C. The mixture was dil... | CCOC(C)OC(C)(C)C(F)(F)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC5CCCCO5)C[C@H](OC5CCCCO5)[C@]4(C)[C@H]3CC[C@]12C | null | null | null |
740,375 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][N:7]([CH3:11])[N:6]=1)=[O:4].C(N(CC)CC)C.[C:19]1([C:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:25]([C:19]2[CH:24]=[CH:23][CH:... | COC(=O)c1nn(C)cc1N | ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-amino-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester (160 mg, 1.03 mmol) in N,N-dimethylformamide (1.0 mL) at 25° C. was treated with triethylamine (0.35 mL, 2.6 mmol) and triphenylmethylchloride (316 mg, 1.13 mmol). Additional N,N-dimethylformamide (2.0 mL) was added to the reaction to aid stirrin... | COC(=O)c1nn(C)cc1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | 91.1 | null |
1,178,857 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:46])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:36](=[O:45])[NH:37][C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[CH2:25][N:26]2[CH2:30][CH2:29][CH:28]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[CH2:27]2)=[CH:20][CH:19]=1)(C... | CCN(CC)C1CCN(CC(C(=O)Nc2ccc(Cl)cc2)c2ccc(/C=C/C(=O)Nc3ccccc3NC(=O)OC(C)(C)C)cc2)C1 | null | null | O=C([O-])O | [Na+] | 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 | 4 | To a solution of (E)-[2-(3-{4-[1-(4-chloro-phenylcarbamoyl)-2-(3-diethylamino-pyrrolidin-1-yl)-ethyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (528 mg, 0.8 mmol) in CH2Cl2 (10 mL) was added CF3COOH (612 uL, 8 mmol). The mixture was stirred for about 4 h, and then NaHCO3 was added to the reaction sy... | CCN(CC)C1CCN(CC(C(=O)Nc2ccc(Cl)cc2)c2ccc(/C=C/C(=O)Nc3ccccc3N)cc2)C1 | null | null | null |
819,595 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [OH:1][CH2:2][C:3](=[O:5])[CH3:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:1][CH2:2][C:3](=[O:5])[CH3:4] | CC(=O)CO | C1=COCCC1 | null | Cc1ccc(S(=O)(=O)[O-])cc1 | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-hydroxy-propan-2-one (95%, 78 g, 1.0 mol), 3,4-dihydro-2H-pyrane (95%, 88.5 g, 1.0 mol) and pyridinium p-toluenesulfonate (25.1 g, 0.1 mol) in THF (1.2 l) is stirred at room temperature for 16 hours. The mixture is diluted with ethyl acetate and repeatedly washed with brine. The organic phase is dried, ... | CC(=O)COC1CCCCO1 | null | 80.8 | null |
71,688 | ord_dataset-520610070b3c4780a03b44c7fcecc28f | null | 1980-01-01T00:10:00 | true | [C:1]([C:3]1[C:8]2[CH2:9][C:10](=O)[C:11]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2].O.[NH2:21][NH2:22]>C(O)C>[C:1]([C:3]1[C:8]2[CH2:9][C:10](=[N:21][NH2:22])[C:11]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2] | N#Cc1cccc2c1CC(=O)c1cc(F)ccc1S2 | 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 | null | The mixture of 0.3 g of 9-cyano-2-fluoro-10,11-dihydrodibenzo[b,f]thiepin-11-one, 0.3 g of 100% hydrazine hydrate and 10 ml of ethanol was heated under reflux on waterbath for 5 hours. The reaction mixture was concentrated to 5 ml to separate crystals on cooling, which was collected by filtration. Recrystallization fro... | N#Cc1cccc2c1CC(=NN)c1cc(F)ccc1S2 | null | 95 | null |
15,808 | ord_dataset-b971427c0b944c56b63bb2356fa8ca69 | null | 1976-01-01T00:11:00 | true | [OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[C:8](OC(=O)C)(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]1)(=[O:10])[CH3:9] | OC1CCCNC1 | CC(=O)OC(C)=O | 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 | 2 | 3-Hydroxypiperidine (0.4 mole) is dissolved in 150 ml. of methylene chloride. The solution is cooled to 10° C. and acetic anhydride (0.46 mole) is added dropwise, maintaining the temperature under 20° C. The reaction mixture is allowed to come to room temperature,for 2 hours. The methylene chloride is evaporated off, a... | CC(=O)N1CCCC(O)C1 | null | null | null |
1,607,512 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=3)=[N:13][CH:14]=2)O1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([N:33]1[CH2:38][CH2:37][NH:36][C:35](=[O:39])[CH2:34]1)(=[O:32])=[O:31]>>[NH2:21][C:18]1[N:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][C:9]([C:24]3[CH:2... | CC1(C)OB(c2ccc(-c3cnc(N)nc3)nc2)OC1(C)C | O=C1CN(S(=O)(=O)c2ccccc2Br)CCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a manner similar to that described in Example 427 using 5-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine and 4-((2-bromophenyl)sulfonyl)piperazin-2-one. MS (ESI): mass calcd. for C19H18N6O3S, 410.12; m/z found, 411.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.... | Nc1ncc(-c2ccc(-c3ccccc3S(=O)(=O)N3CCNC(=O)C3)cn2)cn1 | null | null | null |
1,685,522 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][N:3]=1.O.[OH-].[K+].[C:19](=S)=[S:20]>CCO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[O:7][C:19]([SH:20])=[N:9][N:8]=2)=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[CH:11]=1 | S=C=S | CC(C)Nc1cc(Cl)ncc1C(=O)NN | null | [K+] | [OH-] | 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 | 90 | null | 6-chloro-4-(isopropylamino)nicotinohydrazide (10) (1.5 g, 8.7 mmol) was taken in EtOH (10 mL): H2O (5 mL). Added KOH (13 mmol, 1.5 equiv.) followed by the addition of CS2 (87 mmol, 10 equiv.) to the reaction mixture and heated at 90° C., overnight. The reaction mass was concentrated under reduced pressure to remove sol... | CC(C)Nc1cc(Cl)ncc1-c1nnc(S)o1 | null | null | null |
1,050,455 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].B>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:17][CH2:1... | CC(C)(C)OC(=O)N1CCN(Cc2cccc(-c3cccc(C#N)c3)c2)CC1 | null | null | B | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 1,1-dimethylethyl 4-[(3′-cyano-3-biphenylyl)methyl]-1-piperazinecarboxylate (4.5 g) in THF (30 mL) was treated with borane. THF (47.7 mL, 1M in THF) and the resulting mixture was heated at reflux for 1 hour. After cooling to room temperature, the reaction mixture was quenched with saturated ammonium chlor... | CC(C)(C)OC(=O)N1CCN(Cc2cccc(-c3cccc(CN)c3)c2)CC1 | null | 24.2 | null |
739,893 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | C(OC(=O)[NH:7][CH:8]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:29](=[O:32])[NH:30][CH3:31])[CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[CH2:13][CH:12]1[CH2:33][O:34][CH3:35])=[O:10])(C)(C)C.[Cl:45]CCCl>Cl.O1CCO... | ClCCCl | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)OC(C)(C)C)C(COC)C1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 1.5 | {1-(4-Fluoro-benzyl)2-[2-methoxymethyl-4-(1-methylcarbamoyl-2-naphthalen-2-yl-ethyl)-piperazin-1-yl]-2oxo-ethyl}-carbamic acid tert-butyl ester, 65, is dissolved in 4M HCl in dioxane (60 mL). The reaction mixture is stirred for 90 minutes then 1,2-dichloroethane (60 mL) is added. The solution is concentrated in vacuo t... | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(N)Cc2ccc(F)cc2)C(COC)C1 | null | 98 | null |
3,269 | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | null | 1976-01-01T00:03:00 | true | [OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([O:24][CH3:25])=[O:23])[CH2:3]1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.O.Cl>N1C=CC=CC=1>[CH3:25][O:24]... | COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C | Cc1ccc(S(=O)(=O)Cl)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 96 | 3β-Hydroxy-17β-methoxycarbonyl-5α-androstan-11-one (4.75 g.) and toluene-p-sulphonyl chloride (5 g.) in pyridine (50 ml.) were allowed to stand at room temperature for four days. Water (10 ml.) was added, the resulting solution was stirred for an hour and was then poured into stirred water (1.1). The mixture was acidif... | COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)c5ccc(C)cc5)CC[C@]4(C)[C@H]3C(=O)C[C@]12C | null | null | null |
549,154 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([N+:9]([O-])=O)[CH:8]=1)#[N:2]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:8]=1)[NH2:9])#[N:2] | COc1ccc(C#N)cc1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 8.8 g of Compound 18A and 46.8 g of stannous chloride dihydrate in 250 mL of 95% ethanol was refluxed for 1 hour. The solvent was evaporated off in vacuo and the residue was taken up with 200 mL of water. The mixture was acidified with 37% HCl, then alkalinised with 35% sodium hydroxide and extracted with ... | COc1ccc(C#N)cc1N | null | 94.3 | null |
17,973 | ord_dataset-8ca24382d55b4303bc34393399f4110e | null | 1977-01-01T00:01:00 | true | [Mg].Br[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[CH2:4][CH3:5].[C:14]([C:22]1[CH:39]=[CH:38][C:25]([N:26]([CH2:31][CH2:32][N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[S:27]([CH3:30])(=[O:29])=[O:28])=[CH:24][CH:23]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.O>[CH... | CCC(Br)c1ccc(OC)cc1 | CCN(CC)CCN(c1ccc(C(=O)c2ccccc2)cc1)S(C)(=O)=O | null | [Cl-] | [Mg] | [NH4+] | 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 | null | 16 | Magnesium turnings (10.0 g., 0.411 mole) are employed to prepare the Grignard reagent from 0.333 mole of p-(1-bromopropyl)anisole in 500 ml. of tetrahydrofuran which has been previously dried by distillation for lithium aluminum hydride. The Grignard reaction is initiated by adding a small portion of the p-(1-bromoprop... | CCC(c1ccc(OC)cc1)C(O)(c1ccccc1)c1ccc(N(CCN(CC)CC)S(C)(=O)=O)cc1 | null | null | null |
1,348,713 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [F:1][C:2]([F:21])([F:20])[C@@H:3]([OH:19])[CH2:4][N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1>CO.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:8]2[CH2:7][CH2:6][N:5]([CH2:4][C@H:3]([OH:19])[C:2]([F:21])([F:1])[F:20])[CH2:11][CH2:10][C:9]=2[CH:12]=1 | O=[N+]([O-])c1ccc2c(c1)CCN(C[C@H](O)C(F)(F)F)CC2 | 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 | 0.5 | (S)-1,1,1-Trifluoro-3-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-propan-2-ol (582 mg, 1.91 mmol, 1.0 eq) was placed in methanol (20 mL) and 10% palladium on carbon (58 mg) was added. The reaction was hydrogenated at 25 psi for 30 minutes. The mixture was then filtered through celite and concentrated under reduced... | Nc1ccc2c(c1)CCN(C[C@H](O)C(F)(F)F)CC2 | null | null | null |
1,096,109 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:26]([NH:28][C@H:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C:34]([O:36]CC1C=CC(OC)=CC=1)=[O:35])=[O:27])[NH:16][C:17]([C:19]1[N:23]([CH3:24])[N:22]=[C:21]([CH3:25])[CH:20]=1)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1](... | COc1ccc(COC(=O)[C@@H]2CCC[C@@H]2NC(=O)[C@H](CCCNC(=O)OCc2ccccc2)NC(=O)c2cc(C)nn2C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | To a mixture of 4-methoxybenzyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1,3-dimethyl-1H-pyrazole-5-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (0.50 g) and methylene chloride (5.0 ml) was added trifluoroacetic acid (5.0 ml) under ice-cooling, followed by stirring for 1 hour under ice-cooling. The reaction m... | Cc1cc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)N[C@H]2CCC[C@H]2C(=O)O)n(C)n1 | null | 9.2 | null |
853,404 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13]([OH:28])[C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)OC(C)(C)C)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH:13]([C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH2:5][CH2:4][CH2... | CN(C)CCCNc1cc(C(O)c2ccc(NC(=O)OC(C)(C)C)cc2)ccn1 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of tert-butyl 4-((2-(3-(dimethylamino)propylamino)pyridin-4-yl)(hydroxy)methyl)phenylcarbamate (16 mg, 0.04 mmol) in 1 mL of DCM were added Et3SiH (0.1 mL)/TFA in DCM (10%, 0.2 mL). The mixture was stirred for 1 hr and no reaction was detected by LC-MS. Another 0.1 mL of Et3SiH and 0.8 mL of TFA in DCM (1... | CN(C)CCCNc1cc(C(O)c2ccc(N)cc2)ccn1 | null | 49.9 | null |
224,314 | ord_dataset-1d5bba1436bd42b7a27c43833c25d871 | null | 1991-01-01T00:03:00 | true | [F:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:17]=3)=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.O>C(O)(=O)C.Br>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24]... | CCCCCCCc1ccc(-c2cnc(-c3ccc(OC)c(F)c3)nc2)cc1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | 25 | null | 2.5 g of the 2-(3-fluoro-4-methoxyphenyl)-5-(4-heptylphenyl)pyrimidine obtained in Example 1 was dissolved in a mixture of 200 ml of acetic acid and 100 ml of 47% hydrobromic acid. The obtained solution was heated under reflux for 18 hours. The reaction mixture was allowed to cool to room temperature and 500 ml of wate... | CCCCCCCc1ccc(-c2cnc(-c3ccc(O)c(F)c3)nc2)cc1 | null | 87.2 | null |
432,899 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [C:1]([C:3]1[CH:19]=[CH:18][C:6]([C:7]([N:9]([CH3:17])[CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=O)=[CH:5][CH:4]=1)#[N:2].[C:20]([C:22]1[CH:30]=[CH:29][C:25](C(Cl)=O)=[CH:24][CH:23]=1)#[N:21]>>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([C:7]2[N:9]([CH3:17])[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:20](... | CN(Cc1ccncc1)C(=O)c1ccc(C#N)cc1 | N#Cc1ccc(C(=O)Cl)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 | 4-Cyano-N-methyl-N-(4-picolyl)benzamide The title compound was prepared using the same procedure as described in Example 2, step (b) except using 4-cyanobenzoyl chloride: 1H NMR (CDCl3): d 8.49 (dd, 2H); 7.86-7.04 (m, 6H); 4.70 and 4.43 (two br s, 2H); 3.08 and 2.89 (two br s, 3H). | Cn1c(-c2ccc(C#N)cc2)nc(-c2ccccc2)c1-c1ccncc1 | null | null | null |
728,420 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:27]=[C:28]([NH:32][C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])[CH:29]=[CH:30][CH:31]=2)[CH2:22][CH2:21]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2(... | CC(C)C(=O)Nc1cccc(C2CCN(CCCN)CC2)c1 | O=C(O)C1(c2ccc(Cl)cc2)CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Example 31 was prepared from 1-(4-chlorophenyl)cyclopentanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.45–7.42 (m, 1H), 7.33–7.24 (m, 7H), 6.94 (d, 1H, J=7.1 Hz), 6.58–6.52 (m, 1H), 3.26 (q, 2H, J=6.... | CC(C)C(=O)Nc1cccc(C2CCN(CCCNC(=O)C3(c4ccc(Cl)cc4)CCCC3)CC2)c1 | null | null | null |
672,882 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:20]([F:28])[CH:19]=[CH:18][C:17]=1B(O)O>O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2... | OB(O)c1ccc(F)c(-c2cccnc2)c1F | CC(C)(O)c1ccn2c(Br)cnc2n1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 65 | null | A mixture of 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (256 mg, 1.0 mmol) and 2,4-difluoro-3-(pyridin-3-yl)benzeneboronic acid (352 mg, 1.5 mmol) in tetrahydrofuran (3 ml) and sodium carbonate (1.25 ml of a 2M solution in water, 2.5 mmol) was degassed with nitrogen for 10 min. Tetrakis(triphenylphosphine)palla... | CC(C)(O)c1ccn2c(-c3ccc(F)c(-c4cccnc4)c3F)cnc2n1 | null | null | null |
460,200 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | C(N(CC)CC)C.[CH3:8][S:9]([N:12]([CH3:18])[NH:13][S:14]([CH3:17])(=[O:16])=[O:15])(=[O:11])=[O:10].Cl[C:20]([O:22][CH2:23][CH2:24][Br:25])=[O:21]>CC(C)=O>[CH3:8][S:9]([N:12]([CH3:18])[N:13]([S:14]([CH3:17])(=[O:15])=[O:16])[C:20]([O:22][CH2:23][CH2:24][Br:25])=[O:21])(=[O:10])=[O:11] | O=C(Cl)OCCBr | CN(NS(C)(=O)=O)S(C)(=O)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 18 | 1,2-Bis(methylsulfonyl)-2-(2-bromoethoxycarbonyl)-1-methylhydrazine (compound 8) was synthesized as follows: Triethylamine (1.45 g, 0.014 mol) was added in portions to a stirred solution of 1,2-bis(methylsulfonyl)-1-methylhydrazine (2.02 g, 0.01 mol) and 2-bromoethyl chloroformate (3.49 g, 0.019 mol) in acetone (100 ml... | CN(N(C(=O)OCCBr)S(C)(=O)=O)S(C)(=O)=O | null | null | null |
262,116 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | [CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([C:33]([O:35]C)=[O:34])=[CH:25][CH:24]=2)[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)/[C:12]([O:14]C)=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>C(O)C.O>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[C:32]... | CCCCc1ncc(/C=C(\Cc2cccs2)C(=O)OC)n1Cc1ccc(C(=O)OC)c2ccccc12 | null | null | [K+] | [OH-] | 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 | 25 | 18 | A slurry containing 14.46 g (26.14 mmol) of methyl(E)-3-[2-n-butyl-1-{(4-carbomethoxynaphth-1-yl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate, 8.38 g (2.09 mmol) of potassium hydroxide in a mixture of 165 mL of ethanol and 85 mL of water was stirred at ambient temperature for 18 hours. Concentration under... | CCCCc1ncc(C=C(Cc2cccs2)C(=O)O)n1Cc1ccc(C(=O)O)c2ccccc12 | null | null | null |
1,410,814 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][N:17]=[C:16]3[NH:20][N:21]=[CH:22][C:15]=23)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23]>O1CCOCC1.C(OCC)C>[ClH:23].[ClH:23].[N:11]1([C:14]2[N:19]=[CH:18][N:17]=[C:16]3[NH:20][N:21]=[CH:22][C:15]=23)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1 | CC(C)(C)OC(=O)N1CCN(c2ncnc3[nH]ncc23)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 2 | The 4-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (600 mg, 1.97 mmol) was dissolved in 4 mL of 1,4-dioxane and treated with 10 mL of 4M HCl in 1,4-dioxane at room temperature. The solution was allowed to stir for two hours to afford a light-yellow suspension of product. The solvent ... | c1nc(N2CCNCC2)c2cn[nH]c2n1 | null | 99 | null |
1,647,044 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[O:5])[CH3:2].[O:19]1[CH2:24][CH2:23][CH:22]([CH2:25][NH2:26])[CH2:21][CH2:20]1>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:26][CH2:25][CH:22]1[CH2:23][CH2:24][O:19][CH2:20][CH2:21]1)=[CH:13][C... | CCOC(=O)c1cnc2c(OC)cccc2c1Cl | NCC1CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (265 mg, 1.0 mmol) was treated with C-(tetrahydro-pyran-4-yl)-methylamine (1.5 mmol) following general procedure B to afford 8-methoxy-4-[(tetrahydro-pyran-4-ylmethyl)-amino]-quinoline-3-carboxylic acid ethyl ester (324 mg). 3-Ethyl-7-methoxy-1-(tetrahydro-pyra... | CCOC(=O)c1cnc2c(OC)cccc2c1NCC1CCOCC1 | null | 94.1 | null |
77,740 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [CH2:1](Br)[C:2]#[CH:3].[Mg].[F:6][CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12]>CCOCC>[F:6][CH2:7][C:8]([OH:13])([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][C:2]#[CH:1] | C#CCBr | CCCCC(=O)CF | null | [Mg] | 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 | null | A 0.25 ml. portion of propargyl bromide is added to a stirred suspension of 0.73 g. of magnesium and 6 mg. of mercuric chloride in 7.5 ml. of ether. The reaction is initiated after a few minutes of vigorous stirring at room temperature. A mixture of 3 g. of 80% 1-fluoro-2-hexanone and 3.63 g. of propargyl bromide in 7.... | C#CCC(O)(CF)CCCC | null | null | null |
27,021 | ord_dataset-14866e68bb5b47f5929457eecb4eb3a5 | null | 1977-01-01T00:07:00 | true | P(Cl)(Cl)(Cl)(Cl)[Cl:2].[S:7]([C:11]1[N:12]([CH2:16][C:17]([OH:19])=O)[CH:13]=[CH:14][N:15]=1)([CH3:10])(=[O:9])=[O:8].CN(C)C=O>C(Cl)Cl>[S:7]([C:11]1[N:12]([CH2:16][C:17]([Cl:2])=[O:19])[CH:13]=[CH:14][N:15]=1)([CH3:10])(=[O:9])=[O:8] | ClP(Cl)(Cl)(Cl)Cl | CS(=O)(=O)c1nccn1CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | 10 | null | Phosphorus pentachloride (22.5 g.) dissolved in methylene chloride (150 cc.) is added dropwise and whilst cooling to 5° C., to a suspension of (2-mesyl-imidazol-1-yl)-acetic acid (12.3 g.) in methylene chloride (50 cc.). Dimethylformamide (2 cc.) is added thereafter and the mixture is then heated under reflux for 4 hou... | CS(=O)(=O)c1nccn1CC(=O)Cl | null | 92.5 | null |
1,654,945 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | C[O:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH2:9])[C:4]=1[C:10]([F:13])([F:12])[F:11].Cl>O1CCOCC1>[NH2:9][C:5]1[N:6]=[CH:7][N:8]=[C:3]([OH:2])[C:4]=1[C:10]([F:13])([F:12])[F:11] | COc1ncnc(N)c1C(F)(F)F | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 90 | 3 | To a solution of 6-methoxy-5-(trifluoromethyl)pyrimidin-4-amine (N-3) (420 mg, 2.18 mmol) in 1,4-dioxane (10 mL), concentrated HCl (1.81 mL, 21.8 mmol) is added and the resulting mixture is stirred at 90° C. for 3 h. The mixture is allowed to cool to RT and then concentrated in vacuo to afford the product, 6-amino-5-(t... | Nc1ncnc(O)c1C(F)(F)F | null | null | null |
63,977 | ord_dataset-b1bf0950b5cb430abbb1d80744f5df84 | null | 1980-01-01T00:03:00 | true | [CH:1]1([CH3:13])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([C:10](Cl)=[O:11])[CH2:2]1.[NH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17]>>[CH3:18][C:15]([NH:14][C:10]([CH:3]1[CH:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH2:6][CH:1]([CH3:13])[CH2:2]1)=[O:11])([CH3:19])[CH2:16][OH:17] | CC(C)(N)CO | CC1CCC(C(C)C)C(C(=O)Cl)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | p-Menth-3-oyl chloride (3.0 g.) was reacted with 2-amino-2-methyl-propan-1-ol (3.0 g.) according to the procedure of Example 3. Product N-(1,1-dimethyl-2-hydroxyethyl)-p-menthane-3-carboxamide was obtained as a crystalline solid which was recrystallised from aqueous methanol. M.p. 123°. | CC1CCC(C(C)C)C(C(=O)NC(C)(C)CO)C1 | null | null | null |
509,397 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([OH:18])[CH2:17][CH2:16][C:11]2(OCC[O:12]2)[CH2:10][CH2:9]1.Cl>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([OH:18])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]1 | OC1(c2ccccc2F)CCC2(CC1)OCCO2 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 8-(2-fluorophenyl)-1,4-dioxa-spiro[4.5]decan-8-ol (5.8 g, 23 mmol) in dioxane (100 mL), cooled to 0° C. was added hydrogen chloride (1M in water, 75 ml, 75 mmol). The reaction mixture was stirred for 2 hour at room temperature, extracted with ethyl ether (2×200 mL) and washed with saturated bicarbonate... | O=C1CCC(O)(c2ccccc2F)CC1 | null | null | null |
768,746 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)=[CH:12]O[C:10]=1[C:21]([O:23]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[NH2:31][CH2:32][CH2:33][NH:34]C(=O)OC(C)(C)C>C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)=[CH:12][N:31]2[CH2:32][CH2... | COC(=O)c1occ(-c2nccs2)c(=O)c1OCc1ccccc1 | CC(C)(C)OC(=O)NCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCO | null | null | null | null | null | null | null | null | null | 70 | 1.5 | Methyl 3-benzyloxy-4-oxo-5-(thiazol-2-yl)-4H-pyran-2-carboxylate (1.47 g) was suspended in ethanol (15 ml)-dioxane (15 ml), and tert-butyl (2-aminoethyl)carbamate (0.816 ml) was added. After stirring at 70° C. for 1.5 hr, the solvent was evaporated and 4N hydrochloric acid/dioxane solution (70 ml) and chloroform (10 ml... | O=C1NCCn2cc(-c3nccs3)c(=O)c(OCc3ccccc3)c21 | null | null | null |
1,443,551 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:32])[NH:10][C:11]2[CH:30]=[CH:29][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24]C(C)(C)C)=[O:23])[CH:17]=3)=[CH:13][C:12]=2[F:31])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:3... | CC(C)(C)OC(=O)c1cc(Oc2ccc(NC(=O)Nc3ccc(Cl)c(C(F)(F)F)c3)c(F)c2)ccn1 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 50 | 16 | At room temperature, tert-butyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)picolinate (1.8 g, 3.43 mmol) was dissolved in dichloromethane (15 mL). Trifluoroacetic acid (15 mL) and triethyl silane (0.2 mL) was added. The resulted mixture was heated to 50° C. and stirred for 16 h. The solvent was... | O=C(Nc1ccc(Cl)c(C(F)(F)F)c1)Nc1ccc(Oc2ccnc(C(=O)O)c2)cc1F | null | 91.8 | null |
224,628 | ord_dataset-1d5bba1436bd42b7a27c43833c25d871 | null | 1991-01-01T00:03:00 | true | [C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[CH:24](O)[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Zn]>[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH... | O=C1c2ccccc2C(O)N1CCCN1CC=C(c2ccccc2)CC1 | null | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | An agitated solution of 2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-3-hydroxy-1-isoindolinone (11 g) in acetic acid (80 cc) is heated to a temperature close to 60° C. and 11.3 g of powdered zinc is added in small portions in the course of 10 minutes. The suspension obtained is then heated to a temperature close... | O=C1c2ccccc2CN1CCCN1CC=C(c2ccccc2)CC1 | null | 58.1 | null |
241,581 | ord_dataset-9f54014563f44962b72e288618421b97 | null | 1992-01-01T00:02:00 | true | Cl[CH2:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5]1.[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:16]1([N:22]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH:4]3[O:8][C:7](=[O:9])[N:6]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12]... | O=C1OC(CCCl)CN1c1ccccc1 | c1ccc(N2CCNCC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of Example 2, the title compound was prepared from 5-(2-chloroethyl)-3-phenyl-2-oxazolidinone and 1-phenylpiperazine. | O=C1OC(CCN2CCN(c3ccccc3)CC2)CN1c1ccccc1 | null | null | null |
1,022,400 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[C:9](=O)[CH:10]([CH3:12])[CH3:11].[NH2:14][NH2:15].O>C(O)CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:9]([CH:10]([CH3:12])[CH3:11])=[N:14][NH:15]2 | CC(C)C(=O)c1c(F)cccc1Br | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | OCCO | null | null | null | null | null | null | null | null | null | 160 | null | A mixture of 1-(2-bromo-6-fluoro-phenyl)-2-methyl-propan-1-one (1.1 g, 4.5 mmol) and anhydrous hydrazine (0.17 mL, 5.4 mmol) in ethylene glycol (10 mL) is heated for 16 hours at 160° C. Water is added and the mixture is extracted with CH2Cl2. The combined extracts are dried (MgSO4) and concentrated in vacuo. The residu... | CC(C)c1n[nH]c2cccc(Br)c12 | null | null | null |
1,582,341 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:9][CH:10]=O>CCO>[N:1]1[CH:9]=[CH:10][N:3]2[CH:4]=[CH:5][N:6]=[CH:7][C:2]=12 | Nc1cnccn1 | O=CCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of aminopyrazine (1 g, 10.5 mmol) and chloroacetaldehyde (50% wt in H2O; 1.98 g, 12.6 mmol) in 1.6 mL of EtOH was heated at 90° C. in a sealed tube for 5 h. Upon cooling to ambient temperature, the reaction mixture was concentrated and diluted with dichloromethane (DCM). The organic layer washed with saturat... | c1cn2ccnc2cn1 | null | 64 | null |
567,609 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | [CH3:1][C:2]([SH:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].FC(F)(F)C(O)=O.[CH3:16][O:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[C:19]=1CO>C(Cl)Cl>[CH3:1][C:2]([S:8][C:19]1[C:22]([O:28][CH3:29])=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:18]=1[O:17][CH3:16])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5] | CC(C)(S)CC(=O)O | COc1cc(OC)c(CO)c(OC)c1 | 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 | 5 | 0.08 | To a solution of 3-methyl-3-sulfanylbutanoic acid (Sweetman et al, J. Med Chem.,14:868 (1971), the disclosure of which is incorporated herein by reference in its entirety) (4.6 g, 34 mmol) in methylene chloride (250 mL) under nitrogen and cooled over ice/salt to 5° C. (internal temperature) was added trifluoroacetic ac... | COc1cc(OC)c(SC(C)(C)CC(=O)O)c(OC)c1 | null | 70 | null |
576,659 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [CH2:1]([NH:4][S:5]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1C(=O)C)(=[O:7])=[O:6])[CH:2]=[CH2:3].Cl[Si](C)(C)C.C([OH:28])C>S(=O)(=O)(O)O>[CH2:1]([NH:4][S:5]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1[OH:28])(=[O:7])=[O:6])[CH:2]=[CH2:3] | CCO | C=CCNS(=O)(=O)c1c(Cl)ccc([N+](=O)[O-])c1C(C)=O | null | C[Si](C)(C)Cl | 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 | A solution of N-allyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamide (30 mg, 009 mmol), 0.mL of chlorotrimethylsilane and 2 drops of fuming sulfuric acid in ethanol was heated to reflux for 20 hours. The solvent was evaporated. The residue was diluted with ethyl acetate and washed with water. The organic layer was then dr... | C=CCNS(=O)(=O)c1c(Cl)ccc([N+](=O)[O-])c1O | null | 100 | null |
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