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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
823,929 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[Cl:10][S:11](O)(=[O:13])=[O:12]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:11]([Cl:10])(=[O:13])=[O:12])=[C:4]([O:8][CH3:9])[CH:3]=1 | COc1cccc(Br)c1 | O=S(=O)(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 | 0 | 1 | To chlorosulfonic acid (20 ml) at 0° C. was added dropwise 3-bromoanisole (18.7 g, 0.1 mol) at such a rate that the internal temperature remained below 5° C. The mixture was stirred at 0° C. for 1 hour and added dropwise to crushed ice. The mixture was extracted with ethyl acetate and the combined organic layers were w... | COc1cc(Br)ccc1S(=O)(=O)Cl | null | null | null |
1,725,948 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14].[CH3:16][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH2:24])[CH2:19][CH2:18]1>>[Cl:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13](=[O:15])[CH3:14])=[C:2]2[NH:24][CH2:23][CH:20]1[CH2:21][CH2:22][N:17](... | CN1CCC(CN)CC1 | CC(=O)c1cnc2ccc(Cl)nc2c1Cl | null | null | null | null | null | null | null | 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 procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (250 mg, 1.0 mmol) was reacted with (1-methylpiperidin-4-yl)methanamine (160 mg, 1.3 mmol) to afford the desired product (170 mg, 49%) as a light yellow-brown solid: 1H NMR (500 MHz, CDCl3) δ 11.06 (br s, 1H), 8.95 (s, 1H), 8.10 (d, J=8.8 Hz,... | CC(=O)c1cnc2ccc(Cl)nc2c1NCC1CCN(C)CC1 | null | 51.1 | null |
626,937 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([NH:17][CH2:18][C@@H:19]([OH:21])[CH3:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]([O-])=O.[Na+]>C(O)(=O)C.O.[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([CH:13]=[N:22][N:17]2[CH2:18][C@@H:19]([OH:21])[CH3:20])=[CH:15][CH:16]=1)[C:2]1[CH:7]=[C... | C[C@H](O)CNc1cc(OCc2ccccc2)ccc1C=O | O=N[O-] | null | [Na+] | [Zn] | 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 | 0.83 | To a mixture of the product from Step C (16.0 g, 56.1 mmol) in acetic acid/water (150 mL/30 mL) at 0° C. was added sodium nitrite (7.75 g, 112 mmol) in portions over 40 min. The mixture was stirred for 50 min, cooled (ice bath), and zinc (14.7 g, 224 mmol) was added in portions. After 1 h the suspension was warmed to r... | C[C@H](O)Cn1ncc2ccc(OCc3ccccc3)cc21 | null | 44.3 | null |
206,257 | ord_dataset-dd1de64954674e17b4b690cac09dc67b | null | 1990-01-01T00:04:00 | true | [Cl:1]N1C(=O)CCC1=O.[CH3:9][N:10]1[C:14]2=[CH:15][N:16]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([Cl:31])[CH:29]=4)[CH:24]=[C:17]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:13]2[CH:12]=[N:11]1.O>CN(C)C=O>[Cl:1][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[C:30]2[C:25]=1[CH:24]=[C:17]1[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:1... | CN1N=CN2C1=Cn1c(cc3ccc(Cl)cc31)-c1ccccc12 | O=C1CCC(=O)N1Cl | 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 | 3 | A solution of 1.91 g N-chlorosuccinimide in 45 ml dimethylformamide was added dropwise to a solution of 3.33 g 1-methyl-12-chloro-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine in 100 ml dimethylformamide. The reaction mixture was stirred for three hours at room temperature. Upon addition of water and stirri... | CN1N=CN2C1=Cn1c(cc3c(Cl)cc(Cl)cc31)-c1ccccc12 | null | 31.7 | null |
1,633,419 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([C:33]4[O:34][C:35]([C:38]5[CH:43]=[CH:42][CH:41]=[C:40]([O:44]C)[CH:39]=5)=[N:36][N:37]=4)[CH:17]=[C:18]([N:20]4[C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:26]5[C:21]4=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3... | COc1cccc(-c2nnc(-c3cc(-n4c5ccccc5c5ccccc54)cc(-n4c5ccccc5c5ccccc54)c3)o2)c1 | null | null | BrB(Br)Br | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(C)=O | null | null | null | null | null | null | null | null | null | 0 | 5.5 | To a solution of 2-(3,5-dicarbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole (0.95 g, 1.63 mmol) in dichloromethane (20.0 ml) was dropwise added BBr3 (7.0 ml, 1M in dichloromethane) at −78° C. (dry-ice/acetone) under nitrogen. After addition of BBr3 solution, the reaction was taken to room temperature and kept a... | Oc1cccc(-c2nnc(-c3cc(-n4c5ccccc5c5ccccc54)cc(-n4c5ccccc5c5ccccc54)c3)o2)c1 | null | null | null |
781,771 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | C(OC([N:8]1[CH2:26][CH2:25][N:11]2[C:12](=[O:24])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][C:20]([F:23])([F:22])[F:21])=O)(C)(C)C.[ClH:27]>CCOCC.O>[ClH:27].[F:23][C:20]([F:21])([F:22])[O:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[C:12](=[O:24])[N:11]1[CH2:25][CH2:26][NH:8][CH2:9][C@H:... | CC(C)(C)OC(=O)N1CCN2C(=O)c3c(OC(F)(F)F)cccc3[C@@H]2C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | O | null | null | null | null | null | null | null | null | null | null | 1 | To a stirring solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-7-trifluoromethoxy-pyrazino[2,1-a]isoindol-6(2H)-one (181 mg, 0.5 mmol) in dry ether (5 mL) was added hydrochloric acid (1 mL). The reaction was stirred for 1 h and then conc. in vacuo to a white solid. The solid was dissolved in water and lyophili... | O=C1c2c(OC(F)(F)F)cccc2[C@@H]2CNCCN12 | null | null | null |
888,411 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [CH2:1]([O:4][C@@H:5]1[CH2:10][O:9]C(C)(C)[O:7][C@H:6]1[CH:13]=[CH2:14])C=C.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O>[OH:9][CH2:10][C@H:5]1[C@H:6]([OH:7])[CH:13]=[CH:14][CH2:1][O:4]1 | C=CCO[C@@H]1COC(C)(C)O[C@H]1C=C | null | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of trans-5-allyloxy-2,2-dimethyl-4-vinyl-[1,3]dioxane (48 mg, 0.28 mmol) in MeOH (5 mL) was added a solution of methanolic HCl (0.5 mL, prepared from 0.5 mL conc. HCl in 30 mL of MeOH). The mixture was stirred for 30 min at ambient temperature. Aqueous saturated NaHCO3 (5 mL) was added and the mixture was... | OC[C@@H]1OCC=C[C@H]1O | null | null | null |
1,051,869 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:17]([CH3:18])[C:16]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[C:15]([C:32]#[C:33][Si](C)(C)C)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].Cl>CCO.C1COCC1>[C:32]([C:15]1... | CCCCCCc1cccc(-c2nc(C#C[Si](C)(C)C)c(C(=O)N3CCC(N4CCCC4)CC3)n2C)c1 | null | null | Cl | O=C([O-])[O-] | [K+] | 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 | 25 | 18 | To a solution of 0.52 g (1.00 mmol) of [2-(3-hexyl-phenyl)-3-methyl-5-trimethylsilanylethynyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 12) in 10 ml EtOH:THF 5:1 was added 0.277 g (2.0 mmol) of solid potassium carbonate and the reaction mixture was stirred at RT for 18 hours. It was then p... | C#Cc1nc(-c2cccc(CCCCCC)c2)n(C)c1C(=O)N1CCC(N2CCCC2)CC1 | null | 60.5 | null |
488,541 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | C([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=1)(=O)C.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=1 | COc1ccc(OC(C)=O)cn1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of the 5acetoxy-2-methoxypyridine (600 mg, 3.59 mmol) in MeOH (10 mL) was added 1M aq. NaOH (10 mL, 10 mmol). After stirring at r.t. for 30 min, volatile solvent was removed in vacuo, acidified with HOAc and extracted with CHCl3(3×). The combind CHCl3 extracts were washed with H2O, dried (anhydrous MgSO4)... | COc1ccc(O)cn1 | null | 53.4 | null |
749,232 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4](S(C)=O)[N:3]=1.[O:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1.O>CN1CCCC1=O>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4... | NC1CCOCC1 | COc1ccc(F)cc1C(=O)c1cnc(S(C)=O)nc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | O | null | null | null | null | null | null | null | null | null | null | null | A solution of (4-amino-2-methanesulfinyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanone (235 mg, 0.73 mmol, Example 157) and tetrahydro-pyran-4-ylamine (Combi-Blocks) (260 mg, 2.3 mmol) in N-methylpyrrolidinone (15 ml) was heated for 30 minutes at 100° C. The solution was cooled, poured into water and extracted ... | COc1ccc(F)cc1C(=O)c1cnc(NC2CCOCC2)nc1N | null | null | null |
1,246,768 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[CH:3]=1.[CH:12]1([C:15]2[CH:16]=[CH:17][C:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[N:19][CH:20]=2)[CH2:14][CH2:13]1>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:24]2[CH2:25][CH2:26][N:21]([C:18]3[CH:17]=[CH:16][C:15]([CH:12]4[CH2:14][CH2:13]4)=[CH... | c1cc(N2CCNCC2)ncc1C1CC1 | O=C(O)c1ccc(Br)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By reaction and treatment in the same manner as in Preparation Example 90 and using 4-bromo-2-fluorobenzoic acid (1.2 g) and 1-(5-cyclopropylpyridin-2-yl)piperazine (1.02 g) described in Preparation Example 187, the title compound (1.73 g) was obtained. | O=C(c1ccc(Br)cc1F)N1CCN(c2ccc(C3CC3)cn2)CC1 | null | 85.3 | null |
1,515,658 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [OH:1][CH2:2][C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]([CH3:7])[CH3:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:6][CH:5]([CH3:7])[CH2:4][C@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:2]=[O:1] | CC(C)C[C@@H](CO)NC(=O)OC(C)(C)C | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of (S)-tert-butyl (1-hydroxy-4-methylpentan-2-yl)carbamate (2 g, 9.20 mmol) in DCM (30 mL) was added Dess-Martin Periodinane (5.86 g, 13.81 mmol) at 0° C. The reaction mixture was allowed to stir at RT for 16 h. The reaction mixture was quenched with NaHCO3, diluted with water and extracted in ethyl aceta... | CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C | null | null | null |
799,113 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].N1C=CC=CC=1.[C:27](Cl)(=[O:29])[CH3:28]>C1COCC1>[C:27]([NH:1][C:2]1[CH:10]=[C:9]([C:11]2[C:16]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[... | NC(=O)c1ccc(-c2ncccc2C(F)(F)F)cc1N | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (0.5 mmol) and pyridine (0.55 mmol) in THF (5 ml) add acetyl chloride (0.55 mmol). Stir the mixture 10 minutes at room temperature. Concentrate under vacuum, extract with EtOAc, wash with brine, dry over Na2SO4, and concentrate under vacuum. Triturat... | CC(=O)Nc1cc(-c2ncccc2C(F)(F)F)ccc1C(N)=O | null | null | null |
3,371 | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | null | 1976-01-01T00:03:00 | true | [S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(N(CC)CC)C.[O:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28](Cl)=[O:29])=[CH:25][CH:26]=2)[CH2:21][CH2:20]1>O1CCCC1>[O:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28]([N:9]3[CH2:8][CH2:7][N:6]([C:2]4[S:1][CH:5]=[CH:4][N:3]=4)[CH2:11][CH2:10]3)=[O:29])=[CH:25]... | c1csc(N2CCNCC2)n1 | O=C(Cl)c1ccc2c(c1)CCO2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 60 | null | To a solution of 9 g of 1-(2-thiazolyl) piperazine and 5 g of anhydrous triethylamine in 200 ml of anhydrous tetrahydroduran, there were added dropwise, a solution of 9.1 g of 5-coumaranyl carboxylic acid chloride in 20 ml of tetrahydrofuran. After the completion of the addition, the reaction mixture was heated at 60° ... | O=C(c1ccc2c(c1)CCO2)N1CCN(c2nccs2)CC1 | null | 76.3 | null |
290,889 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[C:18](OC(C)(C)C)(=[O:26])[C:19](OC(C)(C)C)=[O:20].CC(C)([O-])C.[K+].Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:19](=[O:20])[C:18]([OH:26])=[C:10]([C:11]([O:13][C:14]([CH3:17])... | CC(C)(C)OC(=O)CCNc1ccccc1F | CC(C)(C)OC(=O)C(=O)OC(C)(C)C | null | CC(C)(C)[O-] | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 84 | To a solution of the title compound of Example C (5.41 g, 22.6 mmol) in dry THF (100 ml) was added di-tert-butyl oxalate (4.57 g, 22.6 mmol), followed by potassium tert-butoxide (5.07 g, 45.2 mmol) and the resulting dark yellow solution was stirred for 84 h at room temperature. The reaction mixture was then acidified w... | CC(C)(C)OC(=O)C1=C(O)C(=O)N(c2ccccc2F)C1 | null | 47.8 | null |
971,370 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:11]C(=O)OC(C)(C)C.Cl.O1CCOCC1>>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11] | CC(C)(C)OC(=O)Nc1ccc2c(c1Cl)OCO2 | 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 | 5.5 | To a vial containing tert-butyl 4-chlorobenzo[d][1,3]dioxol-5-ylcarbamate (307.2 mg, 1.1 mmol, 1 equiv.) was added 5.5 mL of 4N HCl in dioxane (22 mmol, 20 equiv.). The mixture was stirred at room temperature for 5.5 h, the solvent removed under vacuum, the residue dissolved in ethyl acetate, washed with saturated NaHC... | Nc1ccc2c(c1Cl)OCO2 | null | null | null |
234,372 | ord_dataset-45d20d09e4d64f45bdd419044025b4d3 | null | 1991-01-01T00:09:00 | true | [C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[CH2:26][C@H:25]([CH2:27][OH:28])[CH:24]=[CH:23]2)=[C:15](Cl)[N:14]=1.[OH-].[Na+]>CO>[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[CH2:26][C@H:25]([CH2:2... | Nc1nc(Cl)c2ncn([C@H]3C=C[C@@H](CO)C3)c2n1 | N[C@@H]1C[C@H]1c1ccccc1 | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of trans-2-phenyl cyclopropylamine.HCl (1.02 g, 6 mmol) in methanol (10 ml) was stirred with basic ion exchange resin for 5 minutes. The resin was filtered off and the filtrate was concentrated to a colorless oil. To this was added (±)-(cis)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.549... | Nc1nc(N[C@@H]2C[C@H]2c2ccccc2)c2ncn([C@H]3C=C[C@@H](CO)C3)c2n1 | null | null | null |
619,275 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]3[CH2:11][C:12]4[C:17]([C:9]3=[C:8]([CH:18]=O)[C:7]=2[N:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4.[H-].[Na+].C(OP([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])(OCC)=O)C>C1COCC1>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][CH:31]=[CH:18][C:8]1[C:7]2[N:20]=[C:3]([O:2][CH3:1])[CH... | COc1ccc2c(n1)c(C=O)c1n2Cc2ccccc2-1 | CCOC(=O)CCP(=O)(OCC)OCC | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 10.7 mmol of the compound obtained in Step E of Preparation 1 in 20 ml of anhydrous THF are placed in the presence of 1.2 eq of NaH (60% in oil) in 25 ml of anhydrous THF and of 1.2 eq of ethyl 3-(diethoxyphosphoryl)propanoate. The title compound is obtained after 3 hours' stirring at room temperature and gentle reflux... | CCOC(=O)CC=Cc1c2n(c3ccc(OC)nc13)Cc1ccccc1-2 | null | null | null |
586,228 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26]#[N:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]>>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:25](=[CH:5][C:4]2[CH:7]=[CH:8][C:9]([O:13][CH3:14])=[C:10]([O:11][CH3:12])[C:3]=2[O:2][CH3:1]... | COc1ccc(CC#N)cc1OC | COc1ccc(C=O)c(OC)c1OC | null | null | null | null | null | null | null | 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 A, the reaction was performed with 1.96 g of 2,3,4-trimethoxybenzaldehyde (10 mmol) and 1.77 g 3,4-dimethoxyphenyl-acetonitrile (10 mmol), affording 2-(3,4-dimethoxy-phenyl)-3-(2,3,4-trimethoxy-phenyl)-acrylonitrile as yellow powder (yield 3.2 g, 90%). | COc1ccc(C(C#N)=Cc2ccc(OC)c(OC)c2OC)cc1OC | null | 90 | null |
236,800 | ord_dataset-56e7a343b17a4d6da818127ceb19589d | null | 1991-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[CH2:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[SH:21]>C(O)C>[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21][CH2:13][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([OH:12])=[O:11] | Nc1ccccc1S | C=C(C(=O)O)c1ccc(OC)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 125 ml of ethanol, 8.9 g of 4-methoxy-α-methylene benzeneacetic acid and 5.35 ml of 2-amino thiophenol was refluxed for 7 hours. The ethanol was evaporated off and the residue was crystallized from 500 ml of isopropyl ether to obtain 11 g of the desired product melting at 118° C. and used as is for the fo... | COc1ccc(C(CSc2ccccc2N)C(=O)O)cc1 | null | null | null |
533,752 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:14].[Cl:20][S:21](O)(=[O:23])=[O:22]>>[Cl:20][S:21]([C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:6]([CH3:14])[N:5]([CH2:4][C:3]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:2]=3[Cl:1])[C:9]=2[CH:10]=1)(... | O=S(=O)(O)Cl | Cc1nc2ccccc2n1Cc1ccc(Cl)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 | 80 | 1.5 | In an ice bath, 1-(2,4-dichlorobenzyl)-2-methylbenzimidazole (4.00 g) is added to chlorosulfonic acid (20 ml) and the solution is stirred for 24 hours at room temperature and at 1.5 hours at 80° C. The reaction solution is poured into ice water, precipitated gummy solids are separated through filtration, and thus, a mi... | Cc1nc2ccc(S(=O)(=O)Cl)cc2n1Cc1ccc(Cl)cc1Cl | null | null | null |
1,560,993 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | C(O)(C(F)(F)F)=O.[CH:8]1([N:13]2[C:17]3[N:18]=[C:19]([NH2:22])[N:20]=[CH:21][C:16]=3[C:15]3[CH:23]=[CH:24][N:25]=[CH:26][C:14]2=3)[CH2:12][CH2:11][CH2:10][CH2:9]1.Cl[C:28]1[N:33]=[CH:32][C:31]([S:34]([N:37]2[CH2:42][CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]2)(=[O:36])=[O:35])=[CH:30][CH:29]=1>>[CH:8]1([N:13]2[C:17]... | CC(C)(C)OC(=O)N1CCN(S(=O)(=O)c2ccc(Cl)nc2)CC1 | Nc1ncc2c3ccncc3n(C3CCCC3)c2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | Compound 359 was prepared as a white solid (TFA salt) from compound 4 and compound 360 using chemistry similar to that described in example 200. 1H NMR (500 MHz, CD3OD) δ ppm 9.59 (1 H, s), 9.29 (1 H, s), 8.72-8.78 (2 H, m), 8.63-8.66 (1 H, m), 8.61 (1 H, d), 8.22 (1 H, dd, J=8.8, 2.4 Hz), 5.51 (1 H, quin, J=8.9 Hz), 3... | O=S(=O)(c1ccc(Nc2ncc3c4ccncc4n(C4CCCC4)c3n2)nc1)N1CCNCC1 | null | null | null |
1,126,408 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH:4]([CH3:8])[N:3]1[C:9]1[S:10][C:11]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.Br[CH2:23][CH2:24][O:25][Si](C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:8][CH:4]1[N:3]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]... | CC(C)(C)[Si](C)(C)OCCBr | CC1CNCC(C)N1c1nc2ccc(C(F)(F)F)cc2s1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 60 | 20 | A mixture of 2-(2,6-dimethyl piperazine-1-yl)-6-trifluoromethyl benzothiazole (360 mg), (2-bromoethoxy)-t-butyldimethyl silane (257 uL), potassium carbonate (157 mg) and dimethylformamide (2 mL) was stirred at 60° C. for 20 hours. To the reaction solution was added water and extracted with ethyl acetate. The organic la... | CC1CN(CCO)CC(C)N1c1nc2ccc(C(F)(F)F)cc2s1 | null | 65 | null |
1,265,112 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]3)=[C:15]([O:25][CH3:26])[CH:14]=2)[N:3]=1.[OH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([F:37])([F:36])[F:35]>C(OCC)(=O)C>[CH:9]([O:8][C:6]1[N:7]=[C:2]([O:27][C:28... | Oc1ccccc1C(F)(F)F | COc1cc(Nc2nc(Cl)nc(OC(C)C)n2)ccc1-n1cnc(C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared from (4-chloro-6-isopropoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine and 2-hydroxy benzotrifluoride in analogy to example 3. Chromatography on silica gel using ethyl acetate as an eluent gave the title compound as a colorless solid in 99% yield. | COc1cc(Nc2nc(Oc3ccccc3C(F)(F)F)nc(OC(C)C)n2)ccc1-n1cnc(C)c1 | null | 99 | null |
570,183 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:22])=[C:16]([NH2:21])[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][C:11]2([CH3:24])[CH3:23])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>C(OCC)(=O)C.CCCCCC>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](... | Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)C(C)(C)O2 | O=C(Cl)c1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | By using 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine and 4-chlorobenzoyl chloride, the title compound was synthesized according to Example 1b. Yield: 71%. Melting point: 201-203° C. (Ethyl acetate-hexane) | Cc1c(C)c2c(c(C)c1NC(=O)c1ccc(Cl)cc1)C(c1ccc(C(C)C)cc1)C(C)(C)O2 | null | 71 | null |
1,473,099 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | Cl.[CH:2]1([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[C:21]([C:25]([NH:27][CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)=[O:26])=[C:22]([CH3:24])[NH:23][C:16]=23)[CH2:4][CH2:3]1.C([O:37][C@@H:38]([CH3:42])[C:39](Cl)=[O:40])(=O)C>>[CH:2]1([CH2:5][O:6][C:7... | COc1ccc(OCC2CC2)c(-c2ccnc3c(C(=O)NC4CCNCC4)c(C)[nH]c23)c1 | CC(=O)O[C@@H](C)C(=O)Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-N-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide hydrochloride (example D.f14) and commercially available (2S)-1-chloro-1-oxopropan-2-yl acetate the title compound is obtained as colorless solid. | COc1ccc(OCC2CC2)c(-c2ccnc3c(C(=O)NC4CCN(C(=O)[C@H](C)O)CC4)c(C)[nH]c23)c1 | null | null | null |
1,409,072 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21](Br)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[F:24][C:25]1[C:30](B(O)O)=[CH:29][CH:28]=[CH:27][N:26]=1>>[F:24][C:25]1[C:30]([C:21]2[CH:20]=[CH:19][C:16]3[C:17]4[N:18]=[C:9]([C:8]5[N:4]([CH:1]([CH3:3])[CH... | CC(C)n1ncnc1-c1nc2c(s1)CCOc1cc(Br)ccc1-2 | OB(O)c1cccnc1F | null | null | null | null | null | null | null | 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 for 128, 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene and 2-fluoropyridin-3-ylboronic acid were reacted to give 487 (0.226 g, 20%). 1H NMR (400 MHz, DMSO) δ 8.48 (d, J=8.3, 1H), 8.33-8.18 (m, 2H), 8.12 (s, 1H), 7.54-7.45 (m, 2H), 7.37 (d, J=1.5, 1... | CC(C)n1ncnc1-c1nc2c(s1)CCOc1cc(-c3cccnc3F)ccc1-2 | null | 20 | null |
1,083,416 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[NH2:42][CH:43]1[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([C... | COc1cc(C(=O)O)ccc1Nc1ncc2c(n1)N(C1CCCC1)CC(F)(F)C(=O)N2C | CC(C)(C)OC(=O)N1CCC(N)CC1 | null | null | null | 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 a mixture of 0.25 g (0.56 mmole) of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid (I-22), 0.30 mL (1.7 mmole) of ethyldiisopropyl amine and 0.12 g (0.62 mmole) of 4-amino-1-Boc-piperidine in 4.0 mL of dimethylformamide was added 0.27... | COc1cc(C(=O)NC2CCN(C(=O)OC(C)(C)C)CC2)ccc1Nc1ncc2c(n1)N(C1CCCC1)CC(F)(F)C(=O)N2C | null | 59.6 | null |
1,250,773 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:18]C(=O)OCC2C=CC=CC=2)[C:12]2[O:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:2]1>O1CCCC1.[Pd]>[NH2:18][C@H:11]([C:12]1[O:13][C:14](=[O:17])[NH:15][N:16]=1)[CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1 | O=C(N[C@@H](Cc1c[nH]c2ccccc12)c1n[nH]c(=O)o1)OCc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 24 | A solution of (S)-benzyl 2-(1H-indol-3-yl)-1-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl-carbamate (1.41 g, 3.73 mmol) in anhydrous tetrahydrofuran (100 mL) was mixed with 10% palladium on activated carbon (160 mg) and hydrogenated for 24 h at room temperature and at 3 bar. A further portion of 20% palladium on activ... | N[C@@H](Cc1c[nH]c2ccccc12)c1n[nH]c(=O)o1 | null | null | null |
335,847 | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | null | 1996-01-01T00:08:00 | true | [NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][P:15]([O-:24])[O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:10][CH:9]=1.[ClH:25]>C(Cl)Cl.CCOCC>[ClH:25].[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[P:15]([O:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)(=[O... | [O-]P(Oc1ccc(F)cc1)Oc1ccc(F)cc1 | C1CCNCC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A mixture of piperidine trimer (4.5 g, 54 mmole) and di(4-fluorophenyl)phosphite (14.8 g, 55 mmole) was heated at 90°-100° C. for 3 h under nitrogen. The resulted oil was cooled and dissolved in a mixture of 50 mL CH2Cl2 and 50 mL ether. The solution was saturated with dry HCl, the oil was separated and solidified afte... | O=P(Oc1ccc(F)cc1)(Oc1ccc(F)cc1)C1CCCCN1 | null | 54 | null |
931,885 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [O:1]=[S:2]1(=[O:17])[CH2:7][CH2:6][N:5]([C:8]2[C:14]([F:15])=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=2[F:16])[CH2:4][CH2:3]1.[O-]S(C(F)(F)F)(=O)=O.[Li+].[O:27]1[CH2:33][C@@H:28]1[C:29]([O:31][CH3:32])=[O:30]>C(#N)C>[O:17]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([C:8]2[C:14]([F:15])=[CH:13][C:11]([NH:12][CH2:33][C@@H:28]([OH:27... | Nc1cc(F)c(N2CCS(=O)(=O)CC2)c(F)c1 | COC(=O)[C@H]1CO1 | null | O=S(=O)([O-])C(F)(F)F | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 70 | 7 | A solution of 4-(1,1-dioxidothiomorpholin-4-yl)-3,5-difluoroaniline (EXAMPLE 15, Step 3, 1.30 g, 5.0 mmol) in acetonitrile (7.5 mL) is treated with lithium triflate (0.60 g, 5.0 mmol) and methyl (2R)-2,3-epoxypropanoate (0.51 g, 0.46 mL, 5.0 mmol) and heated to 70° C. for 2 h. At this time an additional amount (1.5 mmo... | COC(=O)[C@H](O)CNc1cc(F)c(N2CCS(=O)(=O)CC2)c(F)c1 | null | 56.5 | null |
1,019,949 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:34][CH2:35][C@@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].[S:48]1[CH:52]=[CH:51][C:50]2[CH:53]=[C:54](O)[CH:55]=[CH:56][C:49]1=2.C(N(CC)CC)C>ClCCl>[S:48]1[CH:52]=[CH:51][C:50]2[CH:53]=[C:54]([O:34][C... | Oc1ccc2sccc2c1 | CC(C)(C)OC(=O)N1CCC[C@H]1CO | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 25 | 8 | Polystyrene supported triphenylphosphine (2.9 mmol/g, 1.70 g, 4.95 mmol) was treated with diisopropylazodicarboxylate (0.779 mL, 3.96 mmol) at 0° C. in anhydrous dichloromethane. A mixture of (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.5 g, 3.3 mmol), benzo[b]thiophen-5-ol (0.5 g, 3.3 mmol) and triethy... | CC(C)(C)OC(=O)N1CCC[C@H]1COc1ccc2sccc2c1 | null | null | null |
1,656,159 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[N:11]2[CH:12]=[C:13]([O:16][C@H:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C@@H:20]([NH2:27])[CH2:19][CH2:18]3)[CH:14]=[CH:15][C:10]2=[N:9][N:8]=1.ClC(Cl)(Cl)C[O:31][C:32](=O)[NH:33][C:34]1[N:35]([C:43]2[CH:48]=[CH:47][C:46]([O:49][Si:50]([CH:57]([CH3:59])[CH3:5... | CN1CCC[C@H]1c1nnc2ccc(O[C@@H]3CC[C@H](N)c4ccccc43)cn12 | CC(C)[Si](Oc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)OCC(Cl)(Cl)Cl)cc1Cl)(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | A mixture of Intermediate E (145 mg, 0.40 mmol) and [5-tert-butyl-2-(3-chloro-4-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester (WO2011/154734A1, which is incorporated herein by reference, 251 mg, 0.420 mmol) in 1,4-dioxane (4 mL) and DIPEA (110 μL, 0.63 mmol) was stirred at 90... | CC(C)[Si](Oc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)N[C@H]2CC[C@@H](Oc3ccc4nnc([C@@H]5CCCN5C)n4c3)c3ccccc32)cc1Cl)(C(C)C)C(C)C | null | 89 | null |
125,924 | ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833 | null | 1985-01-01T00:01:00 | true | [Na].[Cl:2][C:3]1[C:12](Cl)=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:14][CH3:15])[CH:9]=2)[N:4]=1.[CH3:16][OH:17]>>[Cl:2][C:3]1[C:12]([O:17][CH3:16])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:14][CH3:15])[CH:9]=2)[N:4]=1 | CO | COc1ccc2nc(Cl)c(Cl)nc2c1 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 50 | null | In a flame-dried reaction flask under a dry nitrogen atmosphere, there was slowly added a solution consisting of 850 mg. of sodium dissolved in 80 ml. of methanol to a slurry of 7.1 g. of 2,3-dichloro-6-methoxyquinoxaline in 60 ml. of methanol at 50° C. over a period of seven hours. The resulting mixture was then heate... | COc1ccc2nc(Cl)c(OC)nc2c1 | null | null | null |
1,577,484 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][OH:29])=[C:23]([F:30])[CH:22]=3)[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].N1(C(=O)CC2C(F)=C[C:40]([OH:44])=CC=2F)CCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C... | CCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3ccc(CCO)c(F)c3)CC2)nc1 | O=C(Cc1c(F)cc(O)cc1F)N1CCC1 | null | CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 2-[4-(2-{(1S,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-fluorophenyl]ethanol (0.200 g, 0.726 mmol) in 5 ml anhydrous dichloromethane at RT was added a solution of 1-(azetidin-1-yl)-2-(2,6-difluoro-4-hydroxyphenyl) ethanone (0.160 g, 0.871 mmol) in 5 ml anhydrous dichloromethan... | CCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3ccc(CC(=O)OC)c(F)c3)CC2)nc1 | null | null | null |
894,065 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>CCOCC>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5] | O=C(O)c1cc(Cl)cnc1Cl | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | CCOCC | null | null | null | null | null | null | null | null | null | 0 | 1 | A solution of 2,5-dichloronicotinic acid (20.2 g, 0.105 mol, Aldrich) in methanol (500 mL) was cooled to 0° C. and neat thionyl chloride (38 mL, 63 g, 0.525 mol) was added over ˜30 min. The reaction mixture was stirred at 0° C. for 1 hour. The cooling bath was removed, the reaction temperature was allowed to warm to ro... | COC(=O)c1cc(Cl)cnc1Cl | null | 97 | null |
191,102 | ord_dataset-d1bd8c96676b4d21aad27b173c6b4eff | null | 1989-01-01T00:06:00 | true | C([Li])CCC.[C:6]1([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(N(C2C=CC=CC=2)C([O:25][C:26](=O)[C:27]2[CH:32]=[CH:31][C:30]([CH2:33][N:34]3[C:42]4[C:37](=[CH:38][CH:39]=[C:40]([NH:43][C:44](=[O:52])[CH:45]([CH2:50][CH3:51])[CH2:46][CH2:47][CH2:48][CH3:49])[CH:41]=4)[CH:36]=[CH:35]3)=[C:29]([... | CCCCC(CC)C(=O)Nc1ccc2ccn(Cc3ccc(C(=O)OC(=O)N(c4ccccc4)c4ccccc4)cc3OC)c2c1 | CS(=O)(=O)c1ccccc1 | null | O=P([O-])(O)O | [K+] | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of butyllithium (0.86 ml of a 2.3M solution in hexanes) was added to a solution of methyl phenyl sulphone (312 mg) in dry tetrahydrofuran (THF) (5 ml.) at -78° C. After 15 minutes a white suspension formed. To this mixture was then added a solution of 4-[6-(2-ethylhexanamido)indole-1-yl-methyl]-3-methoxybenz... | CCCCC(CC)C(=O)Nc1ccc2ccn(Cc3ccc(C(=O)CS(=O)(=O)c4ccccc4)cc3OC)c2c1 | null | 44.1 | null |
1,750,733 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]([C:32]#[N:33])[N:23]=1>CN1C(=O)CCC1>[C:32]([C:24]1[N:23]=[C:22]([O:1][CH2:2][C@H:3]2[CH2:7][CH2:6][CH2:5][N:4]2[C:8]([O... | CC(C)(C)OC(=O)N1CCC[C@@H]1CO | N#Cc1cc2ccccc2c(Cl)n1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 0 | 1 | A mixture of (R)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (444 mg, 2.206 mmol) and Cs2CO3 (719 mg, 2.206 mmol) in NMP (4 mL) were stirred at 0° C. for 1 hour. Next, 1-chloroisoquinoline-3-carbonitrile (400 mg, 2.121 mmol) was added and the reaction mixture was heated at 140° C. for 15 minutes in a microwav... | CC(C)(C)OC(=O)N1CCC[C@@H]1COc1nc(C#N)cc2ccccc12 | null | null | null |
844,113 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH2:11]([CH:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:28])[C:25](O)=[O:26])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCCCCC>[CH2:11]([CH:18]1[CH2:19][CH2:20][N:21]([C:24](=[O:28])[C:25]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10... | Nc1ccc2[nH]ccc2c1 | O=C(O)C(=O)N1CCC(Cc2ccccc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 5-aminoindole (Aldrich) and (4-benzyl-piperidin-1-yl)-oxo-acetic acid (Example 5b) according to the method described in Example 1c. Melting Point: 68-72° C. (hexane) | O=C(Nc1ccc2[nH]ccc2c1)C(=O)N1CCC(Cc2ccccc2)CC1 | null | null | null |
908,531 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.BrN1C(=[O:21])CCC1=O.C1N2CN3CN(C2)CN1C3>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:21])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1 | O=C1CCC(=O)N1Br | Cc1ccc(-c2ccc(C)cc2)cc1 | null | C1N2CN3CN1CN(C2)C3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | 120 | null | Into CCl4 solvent, 2.4 g(13.3 mmol) of the compound produced in Example 1 (Compound 1) and 0.536 g(3.0 mmol) of N-bromosuccinimide were added and refluxed for 24 hours. After cooled down, the reactant was suction-filtrated and the resultant solution was washed with distilled water and then was dried with anhydrous magn... | Cc1ccc(-c2ccc(C=O)cc2)cc1 | null | 24 | null |
853,867 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [NH2:1][C:2]1[C:3]([C:7]2[NH:23][C:10]3=[CH:11][C:12]4[C:13]([CH3:22])([CH3:21])[C:14](=[O:20])[N:15]([CH2:18][CH3:19])[C:16]=4[CH:17]=[C:9]3[N:8]=2)=[N:4][NH:5][CH:6]=1.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>>[CH2:18]([N:15]1[C:16]2[CH:17]=[C:9]3[N:8]=[C:7]([C:3]4[C:2]([NH:1][C:24](=[O:29])[C:25]([CH3:2... | CCN1C(=O)C(C)(C)c2cc3[nH]c(-c4n[nH]cc4N)nc3cc21 | CC(C)(C)C(=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 | N-[3-(5-Ethyl-7,7-dimethyl-6-oxo-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-1H-pyrazol-4-yl]-2,2-dimethyl-propionamide was prepared using 2-(4-amino-1H-pyrazol-3-yl)-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (250 mg, 0.81 mmol) and pivaloyl chloride (109 μl, 0.89 mmol). The title compound was obta... | CCN1C(=O)C(C)(C)c2cc3[nH]c(-c4n[nH]cc4NC(=O)C(C)(C)C)nc3cc21 | null | null | null |
1,413,390 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].[CH2:10]([S:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)[CH3:11]>>[CH2:10]([S:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[F:9])[CH:16]=[CH:15][CH:14]=1)[CH3:11] | CCSc1cccc(B(O)O)c1 | Nc1ccc(Br)c(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound (430 mg) was prepared from 4-bromo-3-fluoroaniline (300 mg, 1.6 mmol) and 3-(ethylthio)phenylboronic acid (370 mg, 2.0 mmol) as a yellow liquid. | CCSc1cccc(-c2ccc(N)cc2F)c1 | null | 108.7 | null |
349,726 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | [CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[N:10]([CH3:14])[C:9](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[N:8][C:7]=2[N:6]([CH2:24][CH3:25])[C:4]1=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O>CN(C)C=O>[CH2:37]([O:36][C:34]([CH2:33][O:23][C:20]1[CH:1... | CCOC(=O)CCl | CCn1c(=O)c2c(nc(/C=C/c3ccc(O)cc3)n2C)n(CC)c1=O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | Compound 175 (300 mg, 0.88 mmol) obtained in Reference Example 114 was dissolved in 10 ml of dimethyl formamide. To the solution were added 731 mg (5.29 mmol) of potassium carbonate and 0.47 ml (4.41 mmol) of ethyl chloroacetate, and the mixture was stirred at room temperature for 2 hours. Water was added thereto to di... | CCOC(=O)COc1ccc(/C=C/c2nc3c(c(=O)n(CC)c(=O)n3CC)n2C)cc1 | null | 90.9 | null |
1,136,586 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | CC[O-].[Na+].[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH:10]=O.[C:12]([O:21]CC)(=[O:20])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[CH2:18]([O:17][C:15]([C:14](=[CH:10][C:6]1[S:5][CH:9]=[CH:8][CH:7]=1)[CH2:13][C:12]([OH:21])=[O:20])=[O:16])[CH3:19] | O=Cc1cccs1 | CCOC(=O)CCC(=O)OCC | null | CC[O-] | [Na+] | 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 | Sodium ethylate (41.4 g, 0.61 mol) was added under vigorous stirring to a solution of thiophene-2-carbaldehyde (57 g, 0.51 mol) and diethyl succinate (176 g, 1.01 mol) in ethanol (1 L). The reaction mixture was refluxed for 3 h and evaporated in vacuum (˜20 mmHg) at 50° C. until the solvent distillation ceased. The obt... | CCOC(=O)C(=Cc1cccs1)CC(=O)O | null | 49 | null |
986,773 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:18]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:17]3[C:12]([C:13]4[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH2:31](O)[CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][OH:39]>>[Cl:1][C:2]1[CH:3]=[C:4]... | OCCOCCOCCO | N#Cc1ccc(N2N=C3c4ccc(C(=O)O)cc4CCC3C2C2CCCC2)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 | The title compound was prepared from (±)-(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 15 and triethylene glycol according to Method E (yellow solid, 125 mg, 0.226 mmol, 47% yield). ES-HRMS m/z calc. for C30H34ClN3NaO5 (M+Na) 574.2085, found 574.2... | N#Cc1ccc(N2N=C3c4ccc(C(=O)OCCOCCOCCO)cc4CCC3C2C2CCCC2)cc1Cl | null | 47 | null |
167,422 | ord_dataset-fdef1f30cad64430bf05cf108d8004a2 | null | 1988-01-01T00:01:00 | true | [C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:23][CH2:24][NH:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:12]=[CH:13][C:14]=2[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].C(=... | c1ccc(CNCCc2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)cc1 | CCOC(=O)CCCCCBr | null | O=C([O-])[O-] | [I-] | [K+] | 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 suspension of 3,4-bis(phenylmethoxy)-N-phenylmethyl benzeneethanamine (10 g), ethyl 6-bromohexanoate (10.5 g), potassium carbonate (6.34 g) and potassium iodide (1 g) in acetonitrile (250 ml) was heated under reflux for 24 hours. | CCOC(=O)CCCCCN(CCc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1)Cc1ccccc1 | null | null | null |
1,715,168 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[F:10][C:11]1[CH:12]=[C:13](/[CH:18]=[CH:19]/[C:20]([N:22]2[C@H:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][O:24][C:23]2=[O:33])=[O:21])[CH:14]=[C:15]([F:17])[CH:16]=1>C1COCC1>[F:10][C:11]1[CH:12]=[C:13]([C@H:18]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3]... | O=C(/C=C/c1cc(F)cc(F)c1)N1C(=O)OC[C@H]1c1ccccc1 | Fc1ccc([Mg]Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -40 | 1.5 | A solution of 4-fluorophenylmagnesium bromide (29 mL of a 2.0 M solution in THF, 58 mmol) and copper(I) bromide-dimethylsulfide complex (12 g, 59 mmol) in THF (100 mL) under an atmosphere of nitrogen was cooled to −40° C. in a dry ice-acetonitrile bath. To the stirred solution was added a solution of (4R)-3-[(2E)-3-(3,... | O=C(C[C@@H](c1ccc(F)cc1)c1cc(F)cc(F)c1)N1C(=O)OC[C@H]1c1ccccc1 | null | null | null |
1,636,057 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=1)([O-])=O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=1 | O=[N+]([O-])c1ccc2c3ccccc3c3ccccc3c2c1 | null | null | [Pd] | NN | 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 | 2 | 3.1 g (11.3 mmol) of a mixture of 1 and 2-nitrotriphenylene (synthesized according to J. Chem. Soc., 1955, 4482) in about 100 mL of ethanol, 600 mg (0.57 mmol) of Pd/C (10% on activated carbon), and 2.3 g (45.2 mmol) of hydrazine monhydride were charged in a 250 mL round bottle flask. The reaction mixture was heated up... | Nc1ccc2c3ccccc3c3ccccc3c2c1 | null | 100 | null |
725,886 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [NH2:1][C:2]1[S:3][C:4]([C:11]2[CH:20]=[CH:19][C:14]3[O:15][CH2:16][CH2:17][O:18][C:13]=3[CH:12]=2)=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8].ClC(Cl)(Cl)[C:23]([N:25]=C=O)=[O:24].N>O1CCCC1.CO>[NH2:25][C:23]([NH:1][C:2]1[S:3][C:4]([C:11]2[CH:20]=[CH:19][C:14]3[O:15][CH2:16][CH2:17][O:18][C:13]=3[CH:12]=2)=[C:5]([CH3:10... | Cc1c(-c2ccc3c(c2)OCCO3)sc(N)c1C(N)=O | O=C=NC(=O)C(Cl)(Cl)Cl | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 0 | 0.5 | 2-Amino-4-methyl-5-(1,4-benzodioxan-6-yl)-3-thiophencarboxamide (0.44 g) was dissolved in tetrahydrofuran (10 ml), cooled to 0° C. and trichloroacetylisocyanate (0.11 ml) added dropwise with stirring. Stirring was continued for a further 30 minutes at room temperature and then a solution of ammonia in methanol (8 ml of... | Cc1c(-c2ccc3c(c2)OCCO3)sc(NC(N)=O)c1C(N)=O | null | null | null |
462,947 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:3]1.Br[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1>>[CH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:33]=[... | BrCc1ccc2ccccc2c1 | CC(C)(C)OC(=O)N1CCC(c2ccc(CO)cc2)C(O)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In an analogous manner to that described in Example 22(i), by alkylating tert-butyl (3RS,4RS)-3-hydroxy-4-(4-hydroxymethyl-phenyl)-piperidine-1-carboxylate with 2-bromomethylnaphthalene there was obtained tert-butyl (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-[4-(naphthalen-2-ylmethoxymethyl)-phenyl]-piperidine-1-carboxylat... | CC(C)(C)OC(=O)N1CCC(c2ccc(COCc3ccc4ccccc4c3)cc2)C(OCc2ccc3ccccc3c2)C1 | null | null | null |
1,187,055 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]... | Cc1cccc(C)c1-c1nc2ccc(C(O)C(F)(F)F)cc2n1C(=O)OC(C)(C)C | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of 2-(2,6-dimethylphenyl)-6-(2,2,2-trifluoro-1-hydroxyethyl)-benzoimidazole-1-carboxylic acid tert-butyl ester (475 mg) in methylene chloride (15 mL) was added Dess-Martin reagent (527 mg) and the mixture was stirred at ambient temperature for 18 h. The mixture was washed with water and sodium bicarbonate... | Cc1cccc(C)c1-c1nc2ccc(C(=O)C(F)(F)F)cc2n1C(=O)OC(C)(C)C | null | null | null |
1,697,536 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH3:1][C:2]1([O:15][CH2:16][CH2:17][CH:18]=O)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:27][C:28](=[O:30])[CH3:29])C=CC=CC=1.O>C(Cl)Cl>[CH3:1][C:2]1([O:15][CH2:16][CH2:17]/[CH:18]=[CH:27]/[C:28](=[O:30])[CH3:29])[CH2:3][CH2:4][N:5]([C:8]... | CC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CC(C)(C)OC(=O)N1CCC(C)(OCCC=O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of tert-butyl 4-methyl-4-(3-oxopropoxy)piperidine-1-carboxylate (5.7 g, 21.01 mmol) in CH2Cl2 (150 mL) was added 1-(triphenylphosphoranylidene)propan-2-one (8.69 g, 27.3 mmol) and the resulting mixture was stirred at room temp for 16 h. Water was then added and the mixture was extracted with dichlorometha... | CC(=O)/C=C/CCOC1(C)CCN(C(=O)OC(C)(C)C)CC1 | null | 80.2 | null |
883,442 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [C:1]1([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=1.[H-].[Na+]>CN(C)C=O>[C:2]1([C:7]2[N:11]([CH2:12][CH2:10][CH2:9][CH2:15][CH3:14])[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH:3]=[CH:4][C... | c1ccc(-c2nc3ccccc3[nH]2)c(-c2nc3ccccc3[nH]2)c1 | null | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 0.5 | To a flask were added 1.5 g of 2,2′-(1,2-phenylene)bis(1H-benzimidazole) and 30 ml of N,N-dimethylformamide, and the mixture was cooled to 5 C. To this mixture was added 0.48 g of 60% sodium hydride in mineral oil in small portions, and after stirring at 5-10 C for 30 minutes, 2.4 g of 1-1-iodopentane were added. The r... | CCCCCn1c(-c2ccccc2-c2nc3ccccc3n2CCCCC)nc2ccccc21 | null | null | null |
653,203 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[CH3:11]C(C)([O-])C.[K+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:11])=[C:4]([F:10])[CH:3]=1 | CC(C)(C)[O-] | O=Cc1ccc(Br)cc1F | null | C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | [Br-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a stirred suspension of 4-bromo-2-fluoro-benzaldehyde (Aldrich, 2.30 g, 11.3 mmol) and methyltriphenylphosphonium bromide(Aldrich, 4.93 g, 13.6 mmol) in ether (50 mL), potassium tert-butoxide(1.52 g, 13.6 mmol) was added and the mixture was stirred at room temperature for 1 hour. The solid was filtered off and the f... | C=Cc1ccc(Br)cc1F | null | null | null |
273,164 | ord_dataset-ee287d49cb8642e59ae9c3951f746312 | null | 1993-01-01T00:08:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1[O:21][N:20]=[C:19]([C:22](Cl)=[O:23])[CH:18]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[CH3:12][C:11]([C:7]1[CH:8]=[C:9]([C:22]([C:19]2[CH:18]=[C:17]([CH3:16])[O:21][N:20]=2)=[O:23])[CH:10]=[C:5](... | Cc1cc(C(=O)Cl)no1 | CC(C)(C)c1cccc(C(C)(C)C)c1O | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | S=C=S | null | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of 20.6 g (0.1 mole) of 2,6-di-tert-butylphenol and 15.6 g (0.107 mole) of 5-methylisoxazole-3-carboxylic acid chloride in 100 mL of CS2 is added 14.3 g (0.107 mole) of AlCl3 at +5° C. Vigorous stirring is maintained at that temperature for 1 hour and then at room temperature for 1 hour. The CS2 is decant... | Cc1cc(C(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)no1 | null | 14 | null |
348,487 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | [S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([NH2:8])[CH3:7].[CH:9]([C:12]1[N:16]=[C:15]([C:17](OCC)=[O:18])[S:14][N:13]=1)([CH3:11])[CH3:10]>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([NH:8][C:17]([C:15]1[S:14][N:13]=[C:12]([CH:9]([CH3:11])[CH3:10])[N:16]=1)=[O:18])[CH3:7] | CCOC(=O)c1nc(C(C)C)ns1 | CC(N)c1cccs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 80 | 3 | (R/S)-1-Thiophen-2-yl-ethylamine (19.05 g, 0.150 mol) is added to a stirred solution of ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylate (25.0 g, 0.125 mol) in toluene (50 ml) and the mixture is heated to 80° C. for 2 hours. A further portion of (R/S)-1-[(2-thienyl)ethyl]amine (10.0 g, 0.08 mol) is added to the mixtu... | CC(C)c1nsc(C(=O)NC(C)c2cccs2)n1 | null | 63.4 | null |
1,489,115 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | Cl.[O:2]=[C:3]1[NH:12][C:11]2[N:10]=[CH:9][C:8](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:7][C:6]=2[CH2:5][CH2:4]1.Cl.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24][O:25][CH:26]1[CH2:29][NH:28][CH2:27]1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[O:17]=[C:15]([N:28]1[CH2:29][CH:26]([O:25][CH2:24][C:20]2[S:19][CH:23]=[CH:22]... | c1csc(COC2CNC2)c1 | O=C(O)/C=C/c1cnc2c(c1)CCC(=O)N2 | null | CCN=C=NCCCN(C)C | Cl | 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 | 8 | A 16 mL vial flask was successively charged with (2E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (30 mg, 0.12 mmol), DMF (3 mL), 3-(2-thienylmethoxy)azetidine hydrochloride (29 mg, 0.14 mmol; which may be prepared as described in Step 3), DIPEA (48 μL, 0.28 mmol) and EDAC (27 mg, 0.14 ... | O=C1CCc2cc(/C=C/C(=O)N3CC(OCc4cccs4)C3)cnc2N1 | null | 18 | null |
1,262,183 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([S:13][C:14]2[CH:15]=[C:16]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].O>Cl.C1COCC1>[CH:3]([C:4]1[CH:5]=[C:6]([S:13][C:14]2[CH:15]=[C:16]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]... | COC(OC)c1cc(Sc2cccc(NS(=O)(=O)c3ccccc3)c2)ccc1[N+](=O)[O-] | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of N-[3-(3-dimethoxymethyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide (0.027 mol) in 12N HCl (25 mL), THF (75 mL), and water (50 mL) was stirred overnight at room temperature, and then the mixture was extracted with EtOAc. The extract was washed with H2O and then with a saturated Na2CO3 solution. The ... | O=Cc1cc(Sc2cccc(NS(=O)(=O)c3ccccc3)c2)ccc1[N+](=O)[O-] | null | null | null |
763,003 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].[Al+3].[Cl-].[Cl-].[Cl-].[Br:20]Br>C(Cl)Cl>[Br:20][C:11]1[CH:12]=[CH:13][C:5]([O:4][CH2:3][C:2]([F:14])([F:15])[F:1])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8] | O=C(O)c1ccccc1OCC(F)(F)F | BrBr | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 1 | To a solution of 2-(2,2,2-trifluoroethoxy)benzoic acid (22 g) in methylene chloride (100 ml), was added AlCl3 (13.3 g) at 0° C.followed by bromine (16.0 g, 0.1 mol). The reaction mixture was stirred at 0° C. for 1 hour and then at reflux for 2 hours. The solids were filtered and water (50 ml) and ethyl acetate (50 ml) ... | O=C(O)c1cc(Br)ccc1OCC(F)(F)F | null | 94.7 | null |
1,153,803 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [ClH:1].Br[C:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[S:5][C:4]=1[NH2:12]>CO.[Pd]>[ClH:1].[S:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=[C:4]1[NH2:12] | Nc1sc2cccnc2c1Br | 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 | null | 3 | A mixture of compound 145-H, (1.86 g, 6.16 mmol) and 10% Pd/C (0.49 g, 26.3% w/w) in methanol (75 mL) was catalytically hydrogenated on a Parr shaker at 25 psi. After 3 h, the catalyst was filtered, the reaction mixture recharged with 10% Pd/C (0.49 g, 26.3% w/w) and shaken an additional 16 h at 22 psi H2. The reaction... | Nc1cc2ncccc2s1 | null | 56.5 | null |
1,755,624 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1)=[CH:9]2)(=O)[CH2:2][CH2:3][CH3:4].[CH3:28][O:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33].CCN(CC)CC>C(Cl)Cl.Cl[Ti]... | COc1ccc(CN)c(OC)c1 | CCCC(=O)c1ccc2c(c1)cc(C1CCN(C(=O)OC(C)(C)C)C1)n2C | null | Cl[Ti](Cl)(Cl)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 | 25 | 8 | To solution of tert-butyl 3-(5-butyryl-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylate (0.823 g, 2.22 mmol) in DCM (5 mL) was added 2,4-dimethoxybenzylamine (0.38 mL, 2.53 mmol) and NEt3 (0.90 mL, 6.45 mmol). Mixture was cooled to 0° C. before TiCl4 solution (1M DCM, 1.45 mL, 1.45 mmol) was added dropwise via syringe ... | CCCC(=NCc1ccc(OC)cc1OC)c1ccc2c(c1)cc(C1CCN(C(=O)OC(C)(C)C)C1)n2C | null | null | null |
1,619,533 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:13]([C:15]1[N:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)#[N:14].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][S:21]([C:18]3[CH:19]=[N:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=3... | N#Cc1ccc(S(=O)(=O)Cl)cn1 | Nc1cc(F)cc2cccnc12 | null | CN(C)c1ccncc1 | 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 | null | In a similar fashion using route 14 general procedure 27, 6-fluoroquinolin-8-ylamine (Intermediate 48) (125 mg, 0.77 mmol), 6-cyano-pyridine-3-sulfonyl chloride (Intermediate 19) (187 mg, 0.92 mmol), pyridine (121 mg, 1.54 mmol), DMAP (cat.) and DCM (10 ml) gave the title compound (67 mg, 26%) after purification by col... | N#Cc1ccc(S(=O)(=O)Nc2cc(F)cc3cccnc23)cn1 | null | 26.5 | null |
1,260,444 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [CH2:1]([N:8]1[CH2:42][CH2:41][C:11]2([N:15]([C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[C:14](=[O:33])[N:13]=[C:12]2[NH:34][CH2:35][CH:36](OC)OC)[CH2:10][CH:9]1[CH3:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O... | COC(CNC1=NC(=O)N(c2cc(F)ccc2-c2ccc(S(C)(=O)=O)cc2)C12CCN(Cc1ccccc1)C(C)C2)OC | null | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 110 | null | To a solution of 8-benzyl-4-[(2,2-dimethoxyethyl)amino]-1-[4-fluoro-4′-(methylsulfonyl)biphenyl-2-yl]-7-methyl-1,3,8-triazaspiro[4.5]dec-3-en-2-one (50 mg, 0.08 mmol) in toluene (2.0 ml) was added p-toluenesulfonic acid (20 mg, 0.01 mmol). The reaction was sealed and allowed to stir at 110° C. The reaction was purified... | CC1CC2(CCN1Cc1ccccc1)c1nccn1C(=O)N2c1cc(F)ccc1-c1ccc(S(C)(=O)=O)cc1 | null | null | null |
1,293,819 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1.Cl>CC(O)C>[Cl:11][C:12]1[N:17]=[C:16]([NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])[C:15]([Cl:19])=[CH:14][N:13]=1 | Clc1ncc(Cl)c(Cl)n1 | NC(=O)c1ccccc1N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 60 | null | A mixture of 2-aminobenzamide (681 mg, 5.0 mmol), 2,4,5-trichloropyrimidine (2.75 g, 15 mmol, 3 equiv.) and concentrated HCl (aq) (1.72 mL, 20 mmol, 4 equiv.) in 2-propanol (100 mL) is heated at 60° C. for 12 h. The 2-propanol solvent is removed in vacuo. The resulting residue is neutralized to approximately pH=7 by ad... | NC(=O)c1ccccc1Nc1nc(Cl)ncc1Cl | null | null | null |
833,928 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:3]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH2:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]>CO>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH:29][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][NH:8]3)=[C:4... | Clc1nc(N2CCOCC2)c2nc[nH]c2n1 | COc1ccc(CCN)cc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 192.5 | 1 | As shown in Scheme 3 above, a mixture of 2,6-dichloropurine (1.90 g, 10 mmol) and morpholine (2.34 g, 30 mmol) in water (25 mL) was heated under reflux for 15 min. Solidified reaction mixture was cooled to room temperature. Solid was filtered out and washed with water, methanol and ether. The 2-chloro-6-morpholin-4-yl-... | COc1ccc(CCNc2nc(N3CCOCC3)c3nc[nH]c3n2)cc1OC | null | 74.8 | null |
1,070,406 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [O-]CC.[Na+].[CH2:5]([C:9]([NH2:11])=[O:10])[C:6]([NH2:8])=[NH:7].Cl.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)=O>C(O)C>[NH2:7][C:6]1[NH:8][C:15]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)=[CH:14][C:5]=1[C:9]([NH2:11])=[O:10] | O=C(CBr)c1ccc(Br)cc1 | N=C(N)CC(N)=O | null | CC[O-] | Cl | [Na+] | 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 | 0.33 | Under ice-cooling, sodium ethoxide (2.1 g, 30 mmol) was added to a suspension of malonamamidine hydrochloride (4.1 g, 30 mmol) in dehydrated ethanol (50 mL), and then the mixture was stirred for 20 minutes. Moreover, 2,4′-dibromoacetophenone (4.2 g, 15 mmol) was added thereto, and the whole was stirred at room temperat... | NC(=O)c1cc(-c2ccc(Br)cc2)[nH]c1N | null | 8.8 | null |
1,719,833 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[N:22][C:23]=3[NH2:25])[NH:18][N:17]=2)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:33]([C:35]1[O:36][C:37](=[O:60])[C:38]2[C:43]([C:44]=1[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH:51]3[O:55][... | Nc1ncnc2[nH]nc(-c3cc(F)cc(OCc4ccccc4)c3)c12 | CC(Br)c1oc(=O)c2ccccc2c1-c1cccc(C2OC(C)(C)C(C)(C)O2)c1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 60 | 0.25 | In a 100 ml round bottomed flask 3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G18, 400 mg, 1,194 mmol) was dissolved in 7 ml of dry DMF then K2CO3 (254 mg, 1.837 mmol) was added. After stirring for 5 min a solution of 3-(1-bromoethyl)-4-(3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phe... | CC(c1oc(=O)c2ccccc2c1-c1cccc(C2OC(C)(C)C(C)(C)O2)c1)n1nc(-c2cc(F)cc(OCc3ccccc3)c2)c2c(N)ncnc21 | null | 0.1 | null |
1,708,367 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:11](=[O:26])[C@:10]([CH2:28][C:29]([NH:31][NH:32][C:33]([NH2:35])=[O:34])=O)([CH3:27])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@... | CCC(CC)N1C(=O)[C@@](C)(CC(=O)NNC(N)=O)C[C@H](c2cccc(Cl)c2)[C@H]1c1ccc(Cl)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 | 25 | null | 259 mg (0.50 mmol) of 2-(2-((3R,5R,6S)-5-(3-Chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxo-1-(pentan-3-yl)piperidin-3-yl)acetyl)hydrazinecarboxamide (Example 76, Step A) was suspended in 2 N aqueous sodium hydroxide (16 mL) and heated at reflux for 3.25 h. Upon cooling to room temperature, the mixture was acidified wi... | CCC(CC)N1C(=O)[C@@](C)(Cc2n[nH]c(=O)[nH]2)C[C@H](c2cccc(Cl)c2)[C@H]1c1ccc(Cl)cc1 | null | null | null |
970,848 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([NH:19][S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[CH2:13]3)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([NH:19][S:20]([CH:23]([CH3:25])[C... | CC(C)S(=O)(=O)NC1Cc2ccc(-c3cccc([N+](=O)[O-])c3)cc2C1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 24 | A solution of Intermediate 3 (430 mg, 1.19 mmol) in ethanol (10 ml) was treated with 10% palladium on charcoal (paste) (100 mg), and then stirred under an atmosphere of hydrogen at room temperature and pressure for 24 h. The mixture was filtered through a bed of kieselguhr and washed through with ethanol. The filtrate ... | CC(C)S(=O)(=O)NC1Cc2ccc(-c3cccc(N)c3)cc2C1 | null | 81.4 | null |
173,972 | ord_dataset-3844acbccc714c04ab757ec4fca10bd0 | null | 1988-01-01T00:06:00 | true | [CH3:1][NH:2][N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.N1C=CC=CC=1.Cl>O>[CH3:1][NH:2][N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:11]=2[F:13])[C... | C1CNCCN1 | CNn1cc(C(=O)O)c(=O)c2cc(F)c(F)c(F)c21 | 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 | null | A mixture of 1.95 g of 1-methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 3.05 g of anhydrous piperazine and 20 ml of dry pyridine is refluxed for 6 hours. The solvent is stripped off in vacuo, the residue is taken up in 20 ml of water, the pH is brought to 7-8 with half-concentrated hydrochlor... | CNn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)c(F)c21 | null | 74.3 | null |
1,764,477 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [H-].[Na+].[CH3:3][N:4]([CH3:8])[CH2:5][CH2:6][OH:7].[CH2:9](Br)[CH:10]=[CH2:11]>CC(C)=O>[CH2:11]([O:7][CH2:6][CH2:5][N:4]([CH3:8])[CH3:3])[CH:10]=[CH2:9] | C=CCBr | CN(C)CCO | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | Sodium hydride (17.5 g) and dimethyl formaldehyde (400 mL) were added to a 2-L round-bottom flask. After cooling the flask to 0° C. by immersing in an ice bath, 2-dimethylaminoethanol (0.398 mol) was added. After stirring for about 30 minutes and adding allyl bromide (0.4378 mol), the mixture was stirred for 3 hours af... | C=CCOCCN(C)C | null | null | null |
524,502 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | [C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[O:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=O)[CH2:16][CH2:15]1>O1CCCC1>[O:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[CH:3][C:1]#[N:2])[CH2:16][CH2:15]1 | CCOP(=O)(CC#N)OCC | O=C1CCOc2ccccc21 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 0.17 | Diethyl cyanomethylphosphonate (1.15 eq.) is slowly added to a suspension of sodium hydride (1.15 eq.) in anhydrous tetrahydrofuran at 0° C. The reaction medium is stirred for 10 minutes at 0° C. and then cooled to −78° C. 4-Chromanone dissolved in tetrahydrofuran is added. The temperature is then returned slowly to 20... | N#CC=C1CCOc2ccccc21 | null | null | null |
501,276 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:42]=[CH:41][C:13]([C:14]([NH:16][S:17]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33]CC(Cl)(Cl)Cl)=[O:32])=[C:22]([CH3:39])[C:21]=2[CH3:40])(=[O:19])=[O:18])=[NH:15])=[CH:12][CH:11]=1)=[O:5])[CH3:2].O>[Zn].CC(O)=O>[CH2:1]([O:3][C... | CCOC(=O)CCCOc1ccc(C(=N)NS(=O)(=O)c2c(C)cc(OCCCC(=O)OCC(Cl)(Cl)Cl)c(C)c2C)cc1 | null | null | [Zn] | 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 | 3.25 | Zn powder (0.32 g) was added to a mixture of 4-ethoxycarbonylpropoxy-N-{4-[3-(2,2,2-trichloroethoxycarbonyl)propoxy]-2,3,6-trimethylbenzenesulfonyl}benzamidine (0.65 g), water (2 ml), and AcOH (18 ml) under ice-water cooling. The reaction mixture was stirred at room temperature for 3.25 hours, and then evaporated. The ... | CCOC(=O)CCCOc1ccc(C(=N)NS(=O)(=O)c2c(C)cc(OCCCC(=O)O)c(C)c2C)cc1 | null | 32.6 | null |
1,729,056 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [F:1][C:2]([F:23])([F:22])[C:3]([N:5]([C@@H:13]1[CH2:15][C@H:14]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][OH:33]>C(#N)C>[F:23][C:2]([F:1])([F:22])[C:3]([N:5]([CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:31][CH2:32]... | O=C(N(CC1CCNCC1)[C@@H]1C[C@H]1c1ccccc1)C(F)(F)F | OCCBr | 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 | 80 | null | To the solution of 2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide (60 mg, 0.184 mmol) in acetonitrile (10 mL) was added potassium carbonate (76 mg, 0.552 mmol) followed by 2-bromoethanol (29.9 mg, 0.239 mmol). The reaction mixture was heated in the seal tube at 80° C. for 4 hours. The r... | O=C(N(CC1CCN(CCO)CC1)[C@@H]1C[C@H]1c1ccccc1)C(F)(F)F | null | 56 | null |
1,556,471 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]1([N:7]2[C:11]([NH:12][C:13](=[O:21])OC3C=CC=CC=3)=[CH:10][C:9]([C:22]([F:25])([F:24])[F:23])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[N:34]=[CH:33][N:32]=[C:31]2[O:40][C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][CH:47]=1)[NH2:44].C(N(CC)C(C)C)(C... | O=C(Nc1cc(C(F)(F)F)nn1-c1ccccc1)Oc1ccccc1 | COc1cc2ncnc(Oc3cccc(N)c3)c2cc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared as described in Example 159B, using phenyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate from the previous step (0.139 g, 0.4 mmol), 3-(6,7-dimethoxyquinazolin-4-yloxy)aniline from Example 113A (0.119 g, 0.4 mmol), and N,N-diisopropylethylamine (0.3 mL) in THF (6 mL) at 50° C. fo... | COc1cc2ncnc(Oc3cccc(NC(=O)Nc4cc(C(F)(F)F)nn4-c4ccccc4)c3)c2cc1OC | null | 53 | null |
1,625,310 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H-].[Na+].Br[CH2:18][C:19]#[N:20]>CN(C=O)C>[C:19]([CH2:18][N:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:20] | N#CCBr | CCOC(=O)c1cc2c([nH]1)CCCC2 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 1 | A 125-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate 104g (5.76 g, 29.8 mmol) and DMF (50 mL). The solution was cooled to 0° C. using an ice bath. Sodium hydride, NaH (60% dispersion in mi... | CCOC(=O)c1cc2c(n1CC#N)CCCC2 | null | 54.9 | null |
330,167 | ord_dataset-2c460e2ef9934444aaf26fec1f75741f | null | 1996-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([F:23])=[C:18]([O:21]C)[CH:19]=3)[CH2:14][CH2:13][N:12]2[CH3:24])[CH2:10][CH2:9]1.[BrH:25]>C(O)(=O)C>[BrH:25].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([F:23])=[C:18]([OH:21])[CH:19]=3... | COc1cc2c(cc1F)CCN(C)C2C1(c2ccccc2Cl)CC1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1-[1-(2-chlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (18.0 g) in acetic acid (150 ml) and 48% aqueous hydrobromic acid (150 ml) was heated under reflux under argon for 220 minutes. The solvent was removed in vacuo, and the residue dried by azeotropic distillation wit... | CN1CCc2cc(F)c(O)cc2C1C1(c2ccccc2Cl)CC1 | null | null | null |
511,967 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24].Cl>CN(C=O)C>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[C:16]([N+:23]([O-:25])=... | N#Cc1ccc(Cl)c([N+](=O)[O-])c1 | CCOC(=O)CC(=O)OCC | null | Cl | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | Diethyl malonate (44.6ml, 293 mmol) was added dropwise over 1.5 hours to a suspension of sodium hydride (11.7 g of a 60% suspension in mineral oil, 293 mmol) in DMF under argon and the reaction mixture was stirred at ambient temperature for 30 minutes. The resulting solution was added dropwise over 1 hour to a solution... | CCOC(=O)C(C(=O)OCC)c1ccc(C#N)cc1[N+](=O)[O-] | null | 97.2 | null |
1,176,505 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[C:16]3[N:15]=[C:14]([CH3:17])[C:13](=[O:18])[NH:12][C:11]=3[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[S:21][CH3:22].[C:23]([C:27]1[CH:31]=[C:30]([N:32]=[C:33]=[O:34])[N:29]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:28]=1)([CH3:26])([CH3:25])[CH3:24]>>[C:23]([C:27]1[CH:31]... | CC(C)(C)c1cc(N=C=O)n(-c2ccccc2)n1 | CSc1cc(Oc2ccnc3[nH]c(=O)c(C)nc23)ccc1N | null | null | null | null | null | null | null | 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-amino-3-(methylthio)phenoxy)-2-methylpyrido[2,3-b]pyrazin-3(4H)-one and 3-tert-butyl-5-isocyanato-1-phenyl-1H-pyrazole to afford the title compound (45 mg, 51%) as a white solid. | CSc1cc(Oc2ccnc3[nH]c(=O)c(C)nc23)ccc1NC(=O)Nc1cc(C(C)(C)C)nn1-c1ccccc1 | null | 51 | null |
801,483 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | CC12C3(C)[N:6]4[CH2:7][CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][N:13]1[CH2:14][CH:15]([C:17]([O:19]C)=[O:18])[CH2:16][N:3]2[CH2:4][CH2:5]4.Cl>C(O)C>[NH:6]1[CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][NH:13][CH2:14][CH:15]([C:17]([OH:19])=[O:18])[CH2:16][NH:3][CH2:4][CH2:5]1 | COC(=O)C1CN2CCN3CCCN4CCN(C1)C2(C)C34C | 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 | 0 | null | A solution of 0.50 g (1.62 mmol) of compound 3, prepared in example A, stage (b), in 20 ml of absolute ethanol is brought to reflux. 3 ml of a 35% aqueous hydrochloric acid solution are added in small amounts. Reflux is maintained for 48 hours. The mixture is cooled to 0° C. and the precipitate formed is filtered off a... | O=C(O)C1CNCCNCCCNCCNC1 | null | null | null |
1,302,969 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[N:16]1[CH:17]=[CH:18][C:13]([O:12][C@H:9]2[CH2:8][CH2:7][C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[N:14][CH:15]=1 | CCOC(=O)[C@H]1CC[C@H](Oc2ccncn2)CC1 | null | null | [Na+] | [OH-] | 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 | 3 | To a solution of cis/trans-4-(pyrimidin-4-yloxy)-cyclohexanecarboxylic acid ethyl ester (1:1) (0.90 g, 3.6 mmol) in 1,4-dioxane (18 ml) was added 2 M aqueous sodium hydroxide solution (18 ml, 36 mmol). Stirring at room temperature for 3 h was followed by acidification to pH 2-3 with 1 M aqueous hydrogen chloride soluti... | O=C(O)[C@H]1CC[C@H](Oc2ccncn2)CC1 | null | null | null |
700,131 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [Cl:1][C:2]1[C:10]2[CH2:11][CH2:12][N:13](C)[CH2:14][CH2:15][N:8]3[C:9]=2[C:5]([C:6]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:7]=23)=[CH:4][CH:3]=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[Cl:1][C:2]1[C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][N:8]3[C:9]=2[C:5]([C:6]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:7]=23)=[CH:4][CH:3]=... | CN1CCc2c(Cl)ccc3c4c(n(c23)CC1)CCCCC4 | null | null | CC(Cl)OC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 6-chloro-3-methyl-2,3,4,5,10,11,12,13-octahydro-1H,9H-cyclohepta[b][1,4]diazocino[7,8,1-hi]indole (0.30 g, 0.99 mmole) in dichloroethane (80 mL) was added 1-chloroethyl chloroformate (1.2 mL, 10.8 mmole) and the mixture refluxed for 24 hours. The reaction mixture was cooled to room temperature and the ... | Clc1ccc2c3c(n4c2c1CCNCC4)CCCCC3 | null | 97.9 | null |
1,199,211 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [CH2:1]([Mg]Br)[CH2:2][CH2:3][CH:4]=[CH2:5].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12]O>>[CH2:5]=[CH:4][CH2:3][CH2:2][CH2:1][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1] | OCCCCCO | C=CCCC[Mg]Br | null | null | null | null | null | null | null | 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 copper catalyzed coupling reaction of a Grignard reagent with an organic halide, which is commonly referred to as a halide displacement reaction, was first reported in 1971 by Kochi and Tamura (J. Am. Chem. Soc. 1971, 93, 1487, Synthesis 1971, 303, J. Organomet. Chem. 1972, 42, 205). In the Synthesis paper the auth... | C=CCCCCCCCCCCCC=C | null | 81 | null |
134,543 | ord_dataset-b76b52f4448a4eedb28ffcd8f902046a | null | 1985-01-01T00:09:00 | true | Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[C:3]=1[S:12][CH3:13].[CH3:14][OH:15].[OH-].[K+]>O>[CH3:13][S:12][C:3]1[C:4]([O:10][CH3:11])=[N:5][C:6]([O:8][CH3:9])=[N:7][C:2]=1[O:15][CH3:14] | COc1nc(Cl)c(SC)c(OC)n1 | CO | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | Charged into a 100-milliliter, 4-necked flask equipped with a reflux condenser, thermometer and stirrer were 2.2 g of 6-chloro-2,4-dimethoxy-5-methylthiopyrimidine and 40 ml of methanol. They were stirred into a homogeneous solution. Subsequent to an addition of 2.0 g of potassium hydroxide, the resultant mixture was h... | COc1nc(OC)c(SC)c(OC)n1 | null | null | null |
1,282,610 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:13][O:12][C:11]3=[CH:14][C:15]4[CH2:19][CH2:18][O:17][C:16]=4[CH:20]=[C:10]23)[C:2]1=[O:21].Br.Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.BrCC1CCCCO1>>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8... | O=C1Nc2ccccc2C12COc1cc3c(cc12)OCC3 | BrCc1ccccn1 | null | Br | BrCC1CCCCO1 | null | null | null | null | 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 as described in EXAMPLE 4 and making non-critical variations using 6,7-dihydrospiro[benzo[1,2-b:4,5-b′]difuran-3,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, and 2-(bromomethyl)pyridine hydrobromide to replace 2-(bromomethyl)tetrahydro-2H-... | O=C1N(Cc2ccccn2)c2ccccc2C12COc1cc3c(cc12)OCC3 | null | null | null |
16,039 | ord_dataset-b971427c0b944c56b63bb2356fa8ca69 | null | 1976-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]#N)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CN(C)C=O.[BH4-].[Na+].[Br:21][CH2:22][CH2:23]CBr>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:23][CH2:22][Br:21])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12] | N#CSc1ccc(N)c([N+](=O)[O-])c1 | BrCCCBr | null | [BH4-] | [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 | 1 | 5.85 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. dimethylformamide is treated under nitrogen with 1.14 g. sodium borohydride at not greater than 30°. The mixture is stirred for one hour at 15°-20°, then treated with 12 g. of 1,3-dibromopropane at 20°-25°. After a further 3 hours, water is added and the crude p... | Nc1ccc(SCCCBr)cc1[N+](=O)[O-] | null | null | null |
1,749,770 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][C:15]=1[CH3:30].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC>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)... | Clc1ccc2c(Cl)ncnc2c1 | Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1F | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | O | null | null | null | null | null | null | null | null | null | null | null | 4,7-dichloroquinazoline (4.0 g, 20.1 mmol), 2-(4-fluoro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.53 g, 22.1 mmol), sodium carbonate (5.33 g, 50.2 mmol), palladium tetrakis (0.70 g, 0.60 mmol), dimethoxyethane (“DME”) (160 mL), and water (40 mL) were combined in a three neck round bottom flask. A c... | Cc1cc(-c2ncnc3cc(Cl)ccc23)cc(C)c1F | null | 71.1 | null |
849,527 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | Cl.Cl.[CH2:3]([O:5][CH2:6][C@:7]1([C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]2)=[O:14])[CH2:11][CH2:10][C@@H:9]([NH2:12])[CH2:8]1)[CH3:4].[CH3:31][CH:32]1[C:37](=O)[CH2:36][CH2:35][O:34][CH2:33]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=... | CCOC[C@]1(C(=O)N2CCN(c3cc(C(F)(F)F)ccn3)CC2)CC[C@@H](N)C1 | CC1COCCC1=O | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | Cl | [Na+] | 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 | 25 | 8 | To a solution of (1R,3S)-3-(ethoxymethyl)-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentanamine dihydrochloride (100.0 mg, 0.211 mmol), 3-methyltetrahydro-4H-pyran-4-one (72.3 mg, 0.634 mmol) and triethylamine (0.118 mL, 0.845 mmol) in dry methylene chloride (5 mL) was added sodium triacetoxybor... | CCOC[C@]1(C(=O)N2CCN(c3cc(C(F)(F)F)ccn3)CC2)CC[C@@H](N[C@@H]2CCOCC2C)C1 | null | 32.3 | null |
1,038,734 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH3:14].[C:15]([O:19][C:20]([N:22]1[CH2:30][CH2:29][CH2:28][CH:24]([C:25](O)=[O:26])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>>[C:15]([O:19][C:20]([N:22]1[CH2:30][CH2:29][CH2:28][CH:24]([C:25]([NH:1][C:2]2[S:6][C:5]([C:7]3[CH... | CC(C)(C)OC(=O)N1CCCC(C(=O)O)C1 | Cc1nc(-c2ccc(Cl)cc2)sc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using 5-amino-2-(4-chlorophenyl)-4-methylthiazole (197 mg, 0.877 mmol) and 1-(tert-butoxycarbonyl)nipecotic acid (205 mg, 0.877 mmol), the same procedure was followed as in Step 3a of Example 3 to give 115 mg (30%) of the desired compound as a yellow powder. | Cc1nc(-c2ccc(Cl)cc2)sc1NC(=O)C1CCCN(C(=O)OC(C)(C)C)C1 | null | 30.1 | null |
1,207,252 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | C([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:18])=[O:5])=[C:10]([C:16]#[CH:17])[CH:11]=1 | C#Cc1cc(Cl)ccc1OCC(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 8 | A solution of (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3; 500 mg; 1.87 mmol) in DCM (2.5 ml) was treated with a 4 N solution of HCl in dioxane (14 ml; 56 mmol) and stirred overnight. The solvents were removed under reduced pressure, to give the title compound. | C#Cc1cc(Cl)ccc1OCC(=O)O | null | null | null |
419,001 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1C=O.OO.S([O-])(O)=[O:21].[K+]>CO>[CH3:6][O:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1[OH:21] | COc1ccc(C=O)c(OC)c1 | O=S([O-])O | null | O=S(=O)(O)O | OO | [K+] | 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 | Conc. sulfuric acid (0.4 ml) was added to a mixed solution comprising 3.3 g of 2,4-dimethoxybenzaldehyde and 30 ml of methanol, and under ice-cooling, 2.93 ml of 30% hydrogen peroxide aqueous solution was added to the mixture. After stirring at room temperature for 4 hours, a 5% aqueous potassium hydrogen sulfite solut... | COc1ccc(O)c(OC)c1 | null | 69 | null |
679,615 | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | null | 2005-01-01T00:08:00 | true | [CH2:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[C:25]([CH2:31][OH:32])[CH:24]=4)[CH:15]=3)=[C:10]([CH2:33][CH2:34][CH3:35])[CH:9]=2)OCC[O:4]1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O>[OH:32][CH... | CCCc1cc(C2(CC)OCCO2)ccc1-c1cc(CCc2ccc(CO)c(CO)c2)ccc1C | null | null | Cc1ccc(S(=O)(=O)O)cc1 | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 640 mg (1.4 mmol) of (4-{2-[4′-(2-ethyl[1,3]dioxolan-2-yl)-6-methyl-2′-propylbiphenyl-3-yl]ethyl}-2-hydroxymethylphenyl)methanol are placed in 15 ml of acetone and 15 ml of water in a round-bottomed flask. A spatula-tip of p-toluenesulfonic acid is added and the solution is refluxed for 2 hours 30 minutes. At room temp... | CCCc1cc(C(=O)CC)ccc1-c1cc(CCc2ccc(CO)c(CO)c2)ccc1C | null | 49.8 | null |
1,618,419 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:13][CH:14]([F:31])[C:15]1[N:20]=[CH:19][C:18]([C:21]2([CH2:29][NH2:30])[CH2:26][CH2:25][C:24]([F:28])([F:27])[CH2:23][CH2:22]2)=[CH:17][N:16]=1>>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:30][CH2:29][C:21]1([C:18... | COc1cccc(C(=O)O)c1Cl | NCC1(c2cnc(C(F)F)nc2)CCC(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 | From 2-chloro-3-methoxybenzoic acid and (1-(2-(difluoromethyl)pyrimidin-5-yl)-4,4-difluorocyclohexyl)methanamine. LCMS (MH+): m/z=446.1, tR (minutes, Method F)=2.82 | COc1cccc(C(=O)NCC2(c3cnc(C(F)F)nc3)CCC(F)(F)CC2)c1Cl | null | null | null |
129,727 | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | null | 1985-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](Cl)=[O:11].C(N(CC)CC)C.[OH:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C... | Oc1cccnc1 | O=C(Cl)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (3.79 g, 0.01 mole) and triethyl amine (1.01 g, 0.01 mole) in toluene (50 ml) was added 3-hydroxypyridine (0.95 g, 0.01 mole). The temperature exothermed to 33° C. and there was an immediate precipitate. The reaction was then reflu... | O=C(Oc1cccnc1)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-] | null | 70.7 | null |
945,979 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[O:28]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1)[C:22]1[CH:27]=[CH:26][C... | FC(F)(F)c1ccc2ncnc(Cl)c2c1 | Oc1ccccc1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 65 | Example 5, Alternative Preparation, Step 1: A sample of 4-chloro-6-(trifluoromethyl)quinazoline (3.25 g, 13.97 mmol) was dissolved in acetonitrile (60 mL) under N2 atmosphere. The resultant cloudy solution was charged with Cs2CO3 (6.83 g, 20.96 mmol) and phenol (1.578 g, 16.77 mmol) and stirred at room temperature. Aft... | FC(F)(F)c1ccc2ncnc(Oc3ccccc3)c2c1 | null | null | null |
240,509 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][NH2:10])[CH:2]=1.[CH3:11][N:12]([CH3:26])[C:13]1[CH:14]=[C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]2=[C:17]([CH:25]=1)[C:18](S)=[N:19]3>C(O)C>[CH3:11][N:12]([CH3:26])[C:13]1[CH:14]=[C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]2=[C:17]([CH:25]=1)[C:18]([NH:10][CH2:9][C... | NCCCc1cccnc1 | CN(C)c1cc2c3c(cccc3c1)N=C2S | 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 | The reaction of equivalent molar quantities of 3-(3-pyridinyl)propanamine, 4-dimethylaminobenz(cd)indol-2thiol, and mercuric acetate in refluxing ethanol, under the conditions of Example 55 leads to the formation of the title compound. | CN(C)c1cc2c3c(cccc3c1)N=C2NCCCc1cccnc1 | null | null | null |
285,375 | ord_dataset-d63ab258f4634f87bdebbaff0a341c28 | null | 1994-01-01T00:02:00 | true | [Cl:1][C:2]1[N+:7]([O-])=[C:6]([CH3:9])[CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[C:15]([O:18]C(=O)C)(=[O:17])[CH3:16]>C(OCC)(=O)C>[C:15]([O:18][CH2:9][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)(=[O:17])[CH3:16] | CC(=O)OC(C)=O | Cc1cccc(Cl)[n+]1[O-] | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of the 6-chloro-2-methylpyridine-N-oxide prepared in step 1 in 750 mL acetic anhydride was heated at reflux overnight. The reaction was cooled to ambient temperature and poured into saturated aqueous sodium bicarbonate. The mixture was diluted with ethyl acetate and filtered through celite. The layers were s... | CC(=O)OCc1cccc(Cl)n1 | null | null | null |
122,059 | ord_dataset-fea3ada7aaad45a0b4e7922640986af3 | null | 1984-01-01T00:09:00 | true | [N:1]1(C(OC(C)(C)C)=O)C[CH2:63][CH2:62][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:30][C@@H:31]([C:42]([NH:44][C@H:45]([C:50]([N:52]([CH3:61])[C@H:53]([C:58]([NH2:60])=[O:59])[CH2:54][CH2:55][CH2:56][CH3:57])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38... | CC(S)S | CCCC[C@@H](C(N)=O)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C | 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 | CSC | null | null | null | null | null | null | null | null | null | null | null | Condensation of BocPro-DTrp-PheOH (part B of Example 17, 0.700 g.) and HDTrp-Leu-MeNleNH2 (0.520 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocPro-DTrp-Phe-DTrp-Leu-MeNleNH2 in 64% yield. De-t-butoxycarbonylation of BocPro-DTrp-Phe-DTrp-Leu-MeNleNH2 (0.750 g.) using trifluoroacetic acid in dimet... | CCCC[C@@H](C(N)=O)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H]1CCCCN1 | null | null | null |
1,040,042 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([N:15]([CH3:35])[CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C@H:25]([CH2:29][C:30]([O:32]CC)=[O:31])[CH2:24][CH2:23]4)[C:12]([C:36]([F:39])([F:38])[F:37])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[Li+].[OH-].O.[CH2:43]1COC[CH2:44]1>C... | C1CCOC1 | CCOC(=O)C[C@@H]1CCc2cc(OCCCN(C)c3nc(-c4ccc(CC)cc4)ccc3C(F)(F)F)ccc21 | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | null | Following the procedure described in Example 308 and starting with ethyl ((1S)-5-[(3-{[6-(4-ethylphenyl)-3-(trifluoromethyl)-2-pyridinyl](methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 319, 10 mg, 0.018 mmol), LiOH (0.1 mg, 0.004 mmol) in THF (1 mL), MeOH (1 mL), and water (0.5 mL), the title compound... | CCc1ccc(-c2ccc(C(F)(F)F)c(N(C)CCCOc3ccc4c(c3)CC[C@H]4C(CC)C(=O)O)n2)cc1 | null | null | null |
417,153 | ord_dataset-1cb9d78632144c5f8acfc3e9ff388678 | null | 1998-01-01T00:11:00 | true | [C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21](C=O)=[CH:20][CH:19]=1>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][CH:8]([C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[O:7][C:1](=[O:6])[CH:2]=1 | COC(=O)CC(C)=O | COc1ccc(C=O)cc1 | null | [H-] | [Li]CCCC | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 0 | 0.25 | The title compound was prepared as described in General Method 1 using 5 mL of methyl acetoacetate, 2.0 g of NaH 60% dispersion in oil, 25 mL of 2.0M n-butyl lithium in hexane, 7.0 mL of 4-methoxybenzaldehyde and 150 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 15 minutes at 0° C.... | COc1ccc(C2CC(O)=CC(=O)O2)cc1 | null | null | null |
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