original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,369,293 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:18])=[C:6]([CH:17]=1)[C:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:8].[Cl:20][C:21]1[CH:22]=[C:23]([OH:30])[CH:24]=[N:25][C:26]=1[CH:27]1[CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[C:3]([O:30][C:23]2[CH:24]=[N:25][C:26]([CH:27]3[CH2:29][C... | Cc1ccc(OC(=O)c2cc(Cl)c(F)cc2F)cc1 | Oc1cnc(C2CC2)c(Cl)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 3 | 4-Methylphenyl 5-chloro-2,4-difluorobenzoate (Preparation 26, 0.330 g, 1.168 mmol) was added portionwise over 5 minutes to a suspension of 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 69, 0.214 g, 1.262 mmol) and potassium carbonate (0.32 g, 2.315 mmol) in DMSO (5.0 mL). The mixture was stirred at room temperature f... | Cc1ccc(OC(=O)c2cc(Cl)c(Oc3cnc(C4CC4)c(Cl)c3)cc2F)cc1 | null | 57.2 | null |
1,056,009 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([O:39][CH3:40])=[C:6]([C:8]([CH3:38])([CH3:37])[CH2:9][C:10]([OH:36])([C:32]([F:35])([F:34])[F:33])[CH2:11][NH:12][C:13]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]3[C:14]=2[CH:15]=[N:16][N:17]3[C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26](O)=[O:27])[CH:7]=1.[NH2:41][C@@H:42]([C:45]([OH... | COc1ccc(F)cc1C(C)(C)CC(O)(CNc1cc(C)cc2c1cnn2-c1cccc(C(=O)O)c1)C(F)(F)F | N[C@H](CO)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared similarly to Intermediate 4 from 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoic acid and D-serine. | COc1ccc(F)cc1C(C)(C)CC(O)(CNc1cc(C)cc2c1cnn2-c1cccc(C(=O)N[C@H](CO)C(=O)O)c1)C(F)(F)F | null | null | null |
630,709 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [C:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:10])[CH:9]=1)(=[NH:3])[NH2:2].CO[CH:13](OC)[CH2:14][CH:15](OC)OC>CN(C=O)C>[Br:10][C:8]1[CH:7]=[N:6][CH:5]=[C:4]([C:1]2[N:2]=[CH:15][CH:14]=[CH:13][N:3]=2)[CH:9]=1 | N=C(N)c1cncc(Br)c1 | COC(CC(OC)OC)OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 90 | 18 | A mixture of the product of Step B (4.86 g, 20.5 mmol) and 1,1,3,3-tetramethoxypropane (6.59 mL, 40 mmol) in DMF (25 mL) was warmed to 90° C. under N2. After 18 h, the reaction mixture was allowed to cool to 25° C., concentrated in vacuo. Purification of the residue by flash chromatography (EtOAc) afforded the title co... | Brc1cncc(-c2ncccn2)c1 | null | 21.7 | null |
295,988 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | C[O:2][C:3](=[O:25])[C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([NH:15][CH:16]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:14])=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[CH:16]1([NH:15][C:13](=[O:14])[CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:4](=[O:24])[C:3]([OH:25])=[O:2])=[CH:10][CH:9]=2)[CH2:... | COC(=O)C(=O)c1ccc(OCC(=O)NC2CCCCCCC2)cc1 | 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 | 0.25 | A solution of 4-[2-(cyclooctylamino)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.4 g) in methanol (40 mL) was treated with 1N sodium hydroxide solution (1.3 mL), and the mixture was stirred at room temperature for 15 minutes. After the solvents were evaporated under reduced pressure, water (20 mL) was adde... | O=C(COc1ccc(C(=O)C(=O)O)cc1)NC1CCCCCCC1 | null | 21.9 | null |
299,065 | ord_dataset-fb70ed83140e4f53a907d87192ad748c | null | 1994-01-01T00:11:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[C:10]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[C:5]([Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([C:21]2[CH:... | OCc1cncc(Br)c1 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1 | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of 5-bromopyridin-3-ylmethanol (Chem. Pharm. Bull. 1990, 38, 2446) (29 g, 154 mmoL) and tert-butylchlorodiphenylsilane (47.5 g, 173 mmoL) in CH2Cl2 (500 mL) at r.t., there was added imidazole (15.8 g, 232 mmoL). The mixture was stirred for 1 hr. and filtered. The filtrate was evaporated and the residue ch... | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)c1ncc(Br)cc1CO | null | null | null |
1,284,196 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Br[C:2]1[S:6][C:5]([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[C:4]([C:12]([NH:14][CH:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:13])[CH:3]=1.CC1(C)COB([C:39]2[N:43]([CH3:44])[N:42]=[CH:41][CH:40]=2)OC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC... | Cn1nccc1B1OCC(C)(C)CO1 | CC(C)(C)OC(=O)NCC(Cc1ccccc1)NC(=O)c1cc(Br)sc1-c1ccoc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | null | 4 | 1,1-dimethylethyl [2-({[5-bromo-2-(3-furanyl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate (140 mg, 0.277 mmol), 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (54 mg, 0.277 mmol), Pd(PPh3)4 (16 mg, 13.8 μmol) and K2CO3 (153 mg, 1.11 mmol) in dioxane (2.3 mL) and H2O (462 uL) were combined in a sea... | Cn1nccc1-c1cc(C(=O)NC(CNC(=O)OC(C)(C)C)Cc2ccccc2)c(-c2ccoc2)s1 | null | null | null |
1,501,492 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [O:1]=[C:2]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4][CH:3]1C(OCC)=O.[OH-].[Na+].Cl>O1CCOCC1.O>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]1 | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 8 | To a solution 1-tert-butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate (429.1, 19.0 g, 66.6 mmol, 1.00 equiv) in 1,4-dioxane (190 mL) was added dropwise sodium hydroxide (4.00 g, 100 mmol, 1.50 equiv) in water (100 mL). The resulting mixture was stiffed at room temperature overnight. The pH was then adjusted to 4-5 with hyd... | CC(C)(C)OC(=O)N1CCCC(=O)CC1 | null | 77.4 | null |
673,209 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[C:5]([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH3:12])([CH2:17][CH2:18][CH2:1... | Clc1ccc2c(c1)Cc1cc(Cl)ccc1-2 | CCCCCCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2,7-Dichloro-9,9-di(1-hexyl)fluorene is prepared from 2,7-dichlorofluorene and 1-bromohexane following the procedure of Example 1 as colorless crystals (recrystallized from hexane) in 91 percent yield, melting point 66° C. to 67° C. HPLC analysis shows that the sample is 99 percent or greater pure and the spectral data... | CCCCCCC1(CCCCCC)c2cc(Cl)ccc2-c2ccc(Cl)cc21 | null | 91 | null |
228,750 | ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac | null | 1991-01-01T00:06:00 | true | Cl.Cl.C[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[BrH:17]>>[BrH:17].[BrH:17].[OH:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:9][CH:10]=1 | COc1ccc(N2CCNCC2)cc1 | null | null | Br | 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 | 20 | 15 | 1-(4-Hydroxyphenyl)piperezine dihydrobromide may be prepared in the following manner: a 47% aqueous solution of hydrobromic acid (720 cc) is added, over 30 minutes and at a temperature of about 20° C., to 4-(4-methoxyphenyl)piperazine dihydrochloride (70 g). The mixture is heated at boiling point for 4 hours then coole... | Oc1ccc(N2CCNCC2)cc1 | null | null | null |
419,758 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | [Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:18][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[O:17][N:16]=1 | Cc1cc(CCCCO[Si](C)(C)C(C)(C)C)on1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 5-[4-(tert-butyldirnethylsilanyloxy)butyl]-3-methylisoxazole (350 mg in 5 mL dry tetrahydrofuran) at 0° C. was added 1.62 mL of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and the mixture stirred while warming to room temperature. After 16 hours, the mixture was concentrated in vacu... | Cc1cc(CCCCO)on1 | null | 72.9 | null |
958,528 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].Br[CH2:14][C:15](=O)[CH2:16][CH3:17]>C1(C)C=CC=CC=1.O1CCOCC1>[CH2:16]([C:15]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=2)[O:7][CH:14]=1)[CH3:17] | COc1cc(C(N)=O)ccc1O | CCC(=O)CBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 125 | null | To a solution of the amide prepared in Example 171 (460 mg, 2.75 mmol) in toluene (3 mL) and 1,4-dioxane (3 mL) was added 1-bromo-2-butanone (623 mg, 4.13 mmol), and the solution was heated to 125° C. for 18 h. The reaction mixture was cooled to rt, and then concentrated under reduced pressure. Purification by silica g... | CCc1coc(-c2ccc(O)c(OC)c2)n1 | null | 63.4 | null |
1,300,050 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [OH-].[Li+].C[O:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:6]>CO>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:13]([NH:12][C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:5]([OH:6])=[O:4])=[O:23])=[CH:16][CH:17]=1 | COC(=O)c1sccc1NC(=O)Cc1ccc(OC)cc1 | null | null | [Li+] | [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 | null | A 3M lithium hydroxide solution (80 mL) was added to methyl-3-(2-(4-methoxyphenyl)acetamido)thiophene-2-carboxylate (7.30 g, 23.91 mmol) dissolved in methanol. The reaction mixture was refluxed for 2 h, cooled to room temperature and then partitioned between ethyl acetate and H2O. The aqueous layer with acidified with ... | COc1ccc(CC(=O)Nc2ccsc2C(=O)O)cc1 | null | null | null |
160,454 | ord_dataset-41c90677d90b4fa5836ab66e2f5b4f51 | null | 1987-01-01T00:06:00 | true | [CH3:1][C:2]([CH3:13])([CH2:6][S:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:3]([OH:5])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C=CC=CC=1>[CH3:13][C:2]1([CH3:1])[CH2:6][S:7][C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:3]1=[O:5] | CC(C)(CSc1cccs1)C(=O)O | null | null | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | 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 | 100 | 2 | A mixture of 2,2-dimethyl-3-(2-thienylthio)propanoic acid (53.65 g, 0.25 m), diatomaceous earth (54 g) and phosphorus pentoxide (87 g) in toluene (870 ml) was vigorously stirred and heated at 100° C. After 2 hours, additional phosphorous pentoxide (87 g) was added and the mixture was heated for 3 hours more. After filt... | CC1(C)CSc2sccc2C1=O | null | 51 | null |
302,794 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | [CH3:1][C:2]1[S:3][CH:4]=[C:5]2[CH2:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:7][C:6]=12.C1(O)C=CC=CC=1.[BrH:27]>C(O)(=O)C>[BrH:27].[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[CH2:9][NH:8][CH2:7][C:6]=12 | Cc1ccc(S(=O)(=O)N2Cc3csc(C)c3C2)cc1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | Oc1ccccc1 | null | null | null | null | null | null | null | null | null | 90 | null | A mixture of 3.1 g (10.6 mmol) of 1-methyl-5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole and 3.1 g (32.9 mmol) of phenol in 43 ml of a 33% solution of hydrobromic acid in acetic acid, placed in a sealed tube, is heated at 90° C. in a water bath for 3 hours. The reaction mixture is then filtered and poured into 150 ml of ... | Cc1scc2c1CNC2 | null | 27 | null |
771,481 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15]1([CH2:18][OH:19])[CH2:17][CH2:16]1>>[CH:15]1([CH2:18][O:19][C:2]2[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:17][CH2:16]1 | CS(=O)(=O)c1ccc(Cl)c(C(=O)O)c1 | OCC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared in analogy to Example A1 (b) from 2-chloro-5-methanesulfonyl-benzoic acid (Example A1(a)) and cyclopropyl-methanol. The crude material was purified by flash chromatography to yield the title compound as a white solid. MS (m/e): 269.1 ([M−H]−, 100%). | CS(=O)(=O)c1ccc(OCC2CC2)c(C(=O)O)c1 | null | null | null |
1,696,757 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Cl[C:2]1[CH:12]=[C:6]2[N:7]([CH3:11])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=1.[OH:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)=[C:20]([CH:23]=1)[C:21]#[N:22].[H-].[Na+].Cl>CN(C)C=O>[CH3:11][N:7]1[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:... | N#Cc1cc(CO)ccc1Oc1cccc(C(F)(F)F)c1 | CN1CCCn2c1cc(Cl)nc2=O | 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 | To a solution of 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (31 mg, 0.153 mmol) and 5-(hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (49.4 mg, 0.168 mmol) in N, N-dimethylformamide (DMF) (1.5 mL), was added NaH (18.36 mg, 0.459 mmol). The reaction mixture was stirred at rt for 30 mi... | CN1CCCn2c1cc(OCc1ccc(Oc3cccc(C(F)(F)F)c3)c(C#N)c1)nc2=O | null | 50.1 | null |
1,157,701 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:21](O)=[O:22])[N:18]([CH3:20])[N:19]=3)=[C:11]([CH2:24][OH:25])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:26][C:27]1([NH2:31])[CH2:30][O:29][CH2:28]1>>[CH3:26][C:27]1([NH:31][C:21]([C:17]2[N:18]([CH3:20])[N:19]=[C:15]([O:14][CH2:13][C:12]3[C:8](... | CC1(N)COC1 | Cn1nc(OCc2c(-c3ccc(Cl)cc3)noc2CO)cc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described for example 107, 5-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (100 mg, 0.28 mmol) was converted, using 3-methyl-3-oxetanamine instead of 2-amino-2-methyl-1-propanol, to the title compound (39 mg, 32%) which was obtained as a white solid. MS: m/e=433.3 ... | Cn1nc(OCc2c(-c3ccc(Cl)cc3)noc2CO)cc1C(=O)NC1(C)COC1 | null | 32 | null |
343,256 | ord_dataset-4c84bc8a34e1469aa1b156355c91cdcc | null | 1996-01-01T00:10:00 | true | [CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[O:15][C:14](=[O:16])[NH:13][CH:12]2[CH2:17][OH:18])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1.Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[O:15][C:14](=[O:16])[NH:13][CH:12]2[CH2:17][O:18][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:9][CH:... | CS(=O)(=O)Cl | CS(=O)(=O)c1ccc(C2OC(=O)NC2CO)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 0 | null | Compound (H) (200 mg; 0.84 mmols) has been dissolved in anhydrous pyridine (3 ml). The thus obtained solution has been cooled to 0° C. and added with freshly distilled methanesulfonyl chloride (0.06 ml). The solution has been maintained at 0° C. overnight and then diluted with an aqueous solution of hydrochloric acid (... | CS(=O)(=O)OCC1NC(=O)OC1c1ccc(S(C)(=O)=O)cc1 | null | null | null |
487,123 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [C:1]([O:5][C:6]([NH:8][N:9]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:13][CH2:12][C@H:11]([O:14][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3] | CS(=O)(=O)Cl | CC(C)(C)OC(=O)NN1CC[C@H](O)C1 | 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 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | (S)-1-(tert-Butoxycarbonylamino)-3-hydroxypyrrolidine (40 g, 0.21 mol) was dissolved in anhydrous methylene chloride (400 mL), in the presence of N,N-diisopropyl-ethylamine (73 mL, 0.42 mol, 2 equiv.) and cooled using an ice bath. This solution was treated with methanesulfonyl chloride (18 mL, 0.23 mol, 1.1 equiv.) ove... | CC(C)(C)OC(=O)NN1CC[C@H](OS(C)(=O)=O)C1 | null | 66.2 | null |
522,424 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC... | Brc1ccccc1I | COc1ccccc1B(O)O | 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 | CCO | null | null | null | null | null | null | null | null | null | 25 | 0.25 | 2-Bromoiodobenzene (640 μL, 5.0 mmol) was added to a suspension of Pd(PPh3)4 (305 mg, 0.26 mmol) in DME (100 mL) at room temperature under argon. After 15 min at room temperature, a solution of 2-methoxyphenylboronic acid (760 mg, 5.0 mmol) in ethanol (2 mL) was added, followed by aqueous Na2CO3 (2.0 M, 5 mL, 10 mmol).... | COc1ccccc1-c1ccccc1Br | null | 62.6 | null |
1,017,950 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19](O)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][N:23]([CH3:38])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:25]=1>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:1... | O=C(O)C1CCCc2c(OCc3ccccc3)cccc21 | CN(C)c1ccc(CNc2ccccc2)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 | By the reaction and treatment in the same manner as in Example 12 using 5-benzyloxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (0.57 g) and [(4-dimethylaminophenyl)methyl]phenylamine (0.61 g) as starting materials, 5-benzyloxy-N-[(4-dimethylaminophenyl)methyl]-N-phenyl-1,2,3,4-tetrahydronaphthalene-1-carboxamide (... | CN(C)c1ccc(CN(C(=O)C2CCCc3c(OCc4ccccc4)cccc32)c2ccccc2)cc1 | null | 80.8 | null |
1,207,656 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:24]([CH3:25])[C:23]5[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=5[N:21]=4)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][O:10][C:6]=2[C:5](I)=[CH:4][N:3]=1.C([O:35][CH:36](OCC)/[CH:37]=[CH:38]/B1OC(C)(C)C(C)(C)O1)C.C(=O)([O-])[O-].[Na+].[Na+].O.C1... | COc1cc(-c2coc3c(I)cnc(N)c23)ccc1NC(=O)c1nc2ccccc2n1C | CCOC(/C=C/B1OC(C)(C)C(C)(C)O1)OCC | 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 | COCCOC | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of N-[4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-benzimidazole-2-carboxamide (1.50 g, 2.78 mmol) in 1,2-dimethoxyethane (30 mL) and water (15 mL) was reacted 2-[(E)-3,3-diethoxy-1-propenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.42 g, 5.56 mmol), sodium carbonate (1.17 g, 11.12... | COc1cc(-c2coc3c(/C=C/C=O)cnc(N)c23)ccc1NC(=O)c1nc2ccccc2n1C | null | 36.9 | null |
423,713 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][O:18][NH2:19].[C:20]([OH:24])(=[O:23])[CH:21]=O>C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C... | Cc1ccc(Cl)c(Nc2ccccc2CON)c1Cl | O=CC(=O)O | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | 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 | 16 | A solution in THF of O-[2-[(2,6-dichloro-3-methylphenyl)amino]phenylmethyl]hydroxylamine (0.50 g, 1.71 mmol), prepared as in step 3, and glyoxylic acid (0.18 g, 1.99 mmol) in THF was stirred for 16 hours. The solution was then diluted with aqueous citric acid and extracted with ethyl acetate (100 mL). The extract was w... | Cc1ccc(Cl)c(Nc2ccccc2CON=CC(=O)O)c1Cl | null | 34.8 | null |
1,453,457 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH:23]4[CH2:28][C@H:27]([CH3:29])[O:26][C@H:25]([CH3:30])[CH2:24]4)[N:16]=3)[C:12]([Cl:31])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[CH3:32][O:33][CH2:34][CH2:35]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[Na+].[N... | COCCOS(=O)(=O)c1ccc(C)cc1 | C[C@@H]1CC(CNc2cccc(-c3cc(N[C@H]4CC[C@H](N)CC4)ncc3Cl)n2)C[C@H](C)O1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 105 | null | The mixture of N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-(((2R,6S)-2,6-dimethyl tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine Compound 284 (20 mg, 0.045 mmol), p-toluenesulfonic acid 2-methoxyethyl ester (14 mg, 0.06 mmol) and sodium carbonate (9.6 mg, 0.09 mmol) in 1 ml DMSO was heated in a reaction v... | COCCN[C@H]1CC[C@H](Nc2cc(-c3cccc(NCC4C[C@@H](C)O[C@@H](C)C4)n3)c(Cl)cn2)CC1 | null | null | null |
1,707,360 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [N:1]([CH2:4][CH:5]1[CH2:10][CH2:9][C:8]2[C:11]3[C:16]([NH:17][C:18]4[CH:27]=[CH:26][C:21]5[NH:22][C:23](=[O:25])[S:24][C:20]=5[CH:19]=4)=[N:15][CH:14]=[N:13][C:12]=3[S:28][C:7]=2[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N>O1CCCC1>[NH2:1][CH2:4][CH:5]1[CH2:10][CH2:9][C:8]2[C:11]3[C:16]([NH:17][C:18]4[C... | [N-]=[N+]=NCC1CCc2c(sc3ncnc(Nc4ccc5[nH]c(=O)sc5c4)c23)C1 | null | null | N | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 8 | A mixture comprising 1.78 g (4.35 mmol) (RS)-6-{[7-(azidomethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl]amino}-1,3-benzothiazol-2(3H)-one (prepared according to example 19), 70 mL tetrahydrofuran and 2.54 g triphenylphosphine was stirred at 23° C. for 2 hours, 9.3 mL aqueous ammonia (25%) were added and ... | NCC1CCc2c(sc3ncnc(Nc4ccc5[nH]c(=O)sc5c4)c23)C1 | null | 62.3 | null |
22,256 | ord_dataset-19b9e29d593f4660ab77c07b459da9bb | null | 1977-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]([OH:14])[CH3:13])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[C:17](Cl)(=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20]>N1C=CC=CC=1>[C:17]([O:14][CH:12]([CH3:13])[CH2:11][O:10][C:9]1[CH:15]=[CH:16][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=1)(=[O:22])[CH2:18][C... | CC(C)CC(=O)Cl | CCOC(=O)c1ccc(OCC(C)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 3 | Cooling in an ice bath 1.1g (5 mmol) of 1-(p-ethoxycarbonyl-phenoxy)-propan- 2-ol was dissolved in 10 ml of pyridine, and 0.6 g of isovaleroyl chloride was added dropwise to this solution. The mixture was stirred at room temperature for an additional 3 hours. The reaction mixture was treated in the same way as in Examp... | CCOC(=O)c1ccc(OCC(C)OC(=O)CC(C)C)cc1 | null | 104.3 | null |
1,224,402 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | CN1CCCC1=O.Cl[C:9]1[N:10]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:11]2[C:16]([N:17]=1)=[C:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:14]=[C:13]([C:24]1[C:25]([CH3:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=1)[N:12]=2.[NH:36]1[CH2:44][CH2:43][CH:39]([C:40]([NH2:42])=[O:41])[CH2:38][CH2:37]1>O>[NH2:30][C:27]1[N:26... | Cc1nc(N)ncc1-c1nc(N2CCOCC2)c2nc(Cl)n(CC3CC3)c2n1 | NC(=O)C1CCNCC1 | 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 | 120 | 2.5 | N-Methylpyrrolidone (1 ml) was added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-methylpyrimidin-2-amine (100 mg, 0.25 mmol) and isonipecotamide (191 mg, 1.5 mmol) and the resulting mixture was stirred at 120° C. for 2.5 hours. The reaction mixture was left standing to cool followed by the ad... | Cc1nc(N)ncc1-c1nc(N2CCOCC2)c2nc(N3CCC(C(N)=O)CC3)n(CC3CC3)c2n1 | null | 69 | null |
1,583,591 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [NH2:1][C:2]1[C:3]([C:13]([NH:15][NH:16][C:17](=O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)(Cl)Cl>[CH2:18]([C:17]1[O:14][C:13]([C:3]2[C:2]([NH2:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[C:5]([Br:12])... | Nc1cc(C(F)(F)F)c(Br)nc1C(=O)NNC(=O)Cc1ccccc1 | null | null | Cc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 65 | null | To a stirred suspension of 3-amino-6-bromo-N′-(2-phenylacetyl)-5-(trifluoromethyl) picolinohydrazide (106 mg, 0.254 mmol) in CHCl3 (2 ml) was added TEA (142 ul, 1.016 mmol) followed by TsCl (145 mg, 0.762 mmol). The mixture was heated to 65° C. for 3 h. The solvent was removed in vacuo and the resulting brown residue w... | Nc1cc(C(F)(F)F)c(Br)nc1-c1nnc(Cc2ccccc2)o1 | null | null | null |
714,536 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)[N:12]=1.S(Cl)(Cl)=O.[CH3:26][NH2:27]>>[CH3:26][NH:27][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([C:11]2[N:12]=[C:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[S:9][CH:10]... | CN | Cc1ccncc1-c1nc(-c2cccc(C(=O)O)c2)cs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | By the reaction in the same manner as in Example 60 using 3-[2-(4-methyl-pyridin-3-yl)-1,3-thiazol-4-yl]benzoic acid (256 mg), thionyl chloride (0.09 ml) and aqueous methylamine solution (40%, 5 ml), the title compound (191 mg) was obtained as colorless powder crystals. | CNC(=O)c1cccc(-c2csc(-c3cnccc3C)n2)c1 | null | null | null |
1,672,265 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [N:1]([CH2:4][CH:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][O:7][CH2:8][CH3:9])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][O:7][CH2:8][CH3:9] | CCOCC(CN=[N+]=[N-])NC(=O)OC(C)(C)C | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 14 | To a solution of tert-butyl (1-azido-3-ethoxypropan-2-yl)carbamate (1.3 g, 5.4 mmol) in methanol (40 mL) was added palladium on carbon (0.13 g, 10% w/w). The mixture was stirred under a hydrogen (15 psi) atmosphere at room temperature. After 14 hours, the reaction mixture was filtered and concentrated under reduced pre... | CCOCC(CN)NC(=O)OC(C)(C)C | null | null | null |
1,741,951 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH3:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[NH:13][N:12]=[N:11]1.[CH3:16]N(C)C=O.[H-].[Na+].CI>O>[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]1 | COc1cccc(-n2nn[nH]c2=O)c1C | CN(C)C=O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a mixture of the above-mentioned 1-(2-methyl-3-methoxyphenyl)-1,4-dihydrotetrazole-5-one 10.00 g and N,N-dimethylformamide 100 mL was added 55% sodium hydride 2.47 g under ice-cooling. The mixtures were raised to room temperature and were stirred for one hour. To the reaction mixtures was added methyl iodide 3.5 mL ... | COc1cccc(-n2nnn(C)c2=O)c1C | null | null | null |
1,520,956 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH3:1][O:2][CH:3]1[CH:7]([OH:8])[CH2:6][CH2:5][O:4]1.[H-].[Na+].[CH2:11]([O:18][CH2:19][CH2:20]O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C=O)C>[CH2:11]([O:18][CH2:19][CH2:20][O:8][CH:7]1[CH2:6][CH2:5][O:4][CH:3]1[O:2][CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1 | COC1OCCC1O | OCCOCc1ccccc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 2 | A solution of 2-methoxy-tetrahydro-furan-3-ol in DMF 200 mL was added sodium hydride in small portions with stirring at 0° C. for 2 hrs, then 2-Benzyloxy-ethanol was added from the dropping funnel over a period of 1 hour, the resulting mixture was stirred at 25° C. for 15 hrs, it was poured into 400 mL water, EtOAC (1 ... | COC1OCCC1OCCOCc1ccccc1 | null | null | null |
1,182,197 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].[CH:9]([OH:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[O-].[Na+]>Cl>[CH:9]([O:22][CH2:2][CH2:1][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][C... | C=Cc1ccncc1 | OC(c1ccccc1)c1ccccc1 | null | C[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 135 | null | With reference to FIG. 7, to a stirred solution of 4-vinylpyridine 1 (10 g, 95.1 mmol) and benzhydrol 2 (35.04 g, 190 mmol), was added sodium methoxide (1.541 g, 28.5 mmol). The reaction mixture was heated at 130-140° C. for 20 hrs, cooled to RT and acidified with 1 N HCl (150 ml). The solution was extracted with ethyl... | c1ccc(C(OCCc2ccncc2)c2ccccc2)cc1 | null | 31.6 | null |
318,825 | ord_dataset-eb32c2b9cbdf4fc39ce6c9fe0fa11430 | null | 1995-01-01T00:10:00 | true | [C:1]1([C:6]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]2[O:14]CC(C)(C)N=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH2:21].[Na+].[Cl-]>O1CCOCC1>[C:1]1([C:6]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]([OH:14])=[O:21])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1 | CC1(C)COC(c2ccsc2C(=O)c2cccs2)=N1 | O | null | Cl | [Cl-] | [Na+] | 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 | 100 | 8 | 2.8 g of 2-(2-thenoyl)-3-(4,4-dimethyl-2-oxazoline-2-yl)thiophene was added to a solution of 30 ml of concentrated hydrochloric acid, 20 ml of water and 20 ml of dioxane, and the solution was stirred at 100° C. for 8 hours. After cooling the solution, an aqueous NaCl solution was added thereto. The resultant solution w... | O=C(O)c1ccsc1C(=O)c1cccs1 | null | null | null |
570,908 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:6]([N:8]1[CH2:26][CH2:25][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[CH:14]([CH3:23])[NH:13][C:12]2=[O:24])[CH2:10][CH2:9]1)=[O:7].Br[CH2:37][CH:38]=[C:39]([CH3:41])[CH3:40]>>[F:35][C:2]([F:1]... | Cc1ccccc1N1C(C)NC(=O)C12CCN(C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1)CC2 | CC(C)=CCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, MS: m/e=568.2 (M+H+), was prepared in accordance with the general method of example 99 from (rac)-8-(3,5-bis-trifluoromethyl-benzoyl)-2-methyl-1-o-tolyl-1,3,8-triaza-spiro[4.5]decan-4-one and 1-bromo-3-methyl-2-butene. | CC(C)=CCN1C(=O)C2(CCN(C(=O)c3cc(C(F)(F)F)cc(C(F)(F)F)c3)CC2)N(c2ccccc2C)C1C | null | null | null |
557,753 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [N:1]1([C:6]2[CH:30]=[CH:29][C:9]([O:10][C:11]3[CH:12]=[CH:13][C:14]([N+:26]([O-])=O)=[C:15]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:16]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>[Pd].CN(C)C=O>[NH2:26][C:14]1[CH:13]=[CH:12][C:11]([O:10][C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:5]=[CH:4][... | CN(C(=O)OC(C)(C)C)c1cc(Oc2ccc(-n3ccnc3)cc2)ccc1[N+](=O)[O-] | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | In a similar manner to that described in Reference Example 7, a reaction was carried out using t-butyl N-{5-[4-(imidazole-1-yl)phenoxy]-2-nitrophenyl]-N-methylcarbamate (8.8 g), palladium on carbon (10%, 0.8 g) and N,N-dimethylformamide (160 ml) and the reaction mixture was purified to give the title compound (5.7 g). | CN(C(=O)OC(C)(C)C)c1cc(Oc2ccc(-n3ccnc3)cc2)ccc1N | null | 69.9 | null |
1,265,302 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Si:1]([O:8][CH2:9][C@H:10]1[C@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13][C@H:12]([OH:22])[C@@H:11]1[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[Si:1]([O:8][CH2:9][C@H:10]1[C@H:14]([O:15][CH:16... | COC(=O)CCC/C=C\C[C@@H]1[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](OC2CCCCO2)C[C@@H]1O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of methyl (Z)-7-[(1R,2S,3R,5S)-2-(t-butyldimethylsilyloxymethyl)-5-hydroxy-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (25) (109.9 g, 233.5 mmol) in ethyl acetate (450 ml), 5%-palladium on carbon (10.98 g) was added and the mixture was hydrogenated at ambient pressure and at room temperature. The r... | COC(=O)CCCCCC[C@@H]1[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](OC2CCCCO2)C[C@@H]1O | null | 99.7 | null |
1,045,331 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=3[F:24])=[N:13][C:12]=2[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:26][C:27]1([C:31]([O:33][CH3:34])=[O:32])[CH2:30][NH:29][CH2:28]1>>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14]([C:16]3[CH:23]=[CH:22][C:... | O=Cc1ccc(-c2nc3cc(Cc4ccccc4)ccc3s2)c(F)c1 | COC(=O)C1(O)CNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesized according to Scheme B1 and general procedure I from 4-(5-benzylbenzo[d]thiazol-2-yl)-3-fluorobenzaldehyde (0.057 g, 0.16 mmol) and methyl 3-hydroxyazetidine-3-carboxylate (0.031 g, 0.16 mmol) to give methyl 1-((4-(5-benzylbenzo[d]thiazol-2-yl)-3-fluorophenyl)methyl)-3-hydroxyazetidine-3-carboxylate. 1H NMR ... | COC(=O)C1(O)CN(Cc2ccc(-c3nc4cc(Cc5ccccc5)ccc4s3)c(F)c2)C1 | null | null | null |
1,058 | ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad | null | 1976-01-01T00:01:00 | true | [NH2:1][C:2]1[O:3][C:4]2[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=2[C:6](=[O:10])[C:7]=1[C:8]#[N:9].S(=O)(=O)(O)[OH:16]>O>[NH2:1][C:2]1[O:3][C:4]2[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=2[C:6](=[O:10])[C:7]=1[C:8]([NH2:9])=[O:16] | N#Cc1c(N)oc2ccccc2c1=O | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | -- A mixture of 1.5 g of 2-amino-4-oxo-4H-1-benzopyran-3-carbonitrile and 7 ml of 80% sulfuric acid is heated for 1 hour on the steam bath. The mixture is cooled, poured into water, and the solid filtered and recrystallized from ethanol, mp 264°-6°C. | NC(=O)c1c(N)oc2ccccc2c1=O | null | null | null |
426,975 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | C[O:2][C:3](=[O:28])[CH2:4][N:5]1[C:11](=[O:12])[C@@H:10]([NH:13][C:14](=[O:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][NH:8][C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]1=2.O.[OH-].[Li+]>CO.O>[C:17]1([CH2:16][CH2:15][C:14]([NH:13][C@@H:10]2[C:11](=[O:12])[N:5]([CH2:4][C:3]([OH:28])=[O:2])[C:... | COC(=O)CN1C(=O)[C@@H](NC(=O)CCc2ccccc2)CNc2ccccc21 | null | 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 | 25 | 4 | (3(S)-(3-Phenylpropionylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)acetic acid methyl ester (104a) was dissolved in 90% methanol. Lithium hydroxide hydrate was added to the reaction and the reaction was stirred at room temperature for 4 h. The reaction was evaporated in vacuo to give a white solid. This... | O=C(O)CN1C(=O)[C@@H](NC(=O)CCc2ccccc2)CNc2ccccc21 | null | 88 | null |
1,344,963 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [OH:1][B:2]1[C:6]2[CH:7]=[C:8](/[CH:11]=[N:12]/O)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:15])([CH3:14])[O:3]1.CO>CC(O)=O.[Zn]>[NH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]2[C:4]([CH3:15])([CH3:14])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1 | CC1(C)OB(O)c2cc(/C=N/O)ccc21 | null | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CO | null | null | null | null | null | null | null | null | null | 40 | 4 | To a solution of crude compound (E)-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde oxime (47.4 mmol) in AcOH (60 mL) at rt was added zinc dust (12.3 g, 190 mmol). The reaction mixture was stirred at 40° C. for 4 h under argon atmosphere. Methanol was added and the mixture was filtered over Celi... | CC1(C)OB(O)c2cc(CN)ccc21 | null | null | null |
1,484,078 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1 | O=S(Cl)Cl | Cc1ccc(CO)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 0.08 | A mixed solution of (5-methyl-pyridine-2-yl)-methanol (500 mg, 4.1 mmol) described in Manufacturing Example 11-1-1, thionyl chloride (0.59 mL, 8.1 mmol) and methylene chloride (10 mL) was stirred for 5 minutes under reflux. The reaction solution was cooled to room temperature and concentrated under a reduced pressure. ... | Cc1ccc(CCl)nc1 | null | 75.8 | null |
1,692,754 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21](O)=[C:20]([C:25]2[NH:26][C:27]3[C:32]([C:33]=2[Cl:34])=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:19]=1>C1(C)C=CC=CC=1>[Br:17][C:18]1[CH:23]=[CH:22][C:21]2[O:5][CH:4]([CH:1]3[CH2:3][CH2:2]3)[N:26]3[C:27]4[CH:28]=[CH:29][CH:30]=[C... | Oc1ccc(Br)cc1-c1[nH]c2ccccc2c1Cl | O=CC1CC1 | 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 | 15 | Cyclopropanecarbaldehyde (70 mg, 1.0 mmol) and PTSA (17 mg, 0.1 mmol) were added to a solution of 4-bromo-2-(3-chloro-1H-indol-2-yl)phenol (110 mg, 0.34 mmol) in toluene (2 mL). The mixture was allowed to stir at 110° C. for about 15 hours. The reaction solution was extracted by EtOAc, and the combined organic layers w... | Clc1c2n(c3ccccc13)C(C1CC1)Oc1ccc(Br)cc1-2 | null | 31.4 | null |
303,409 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | [NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13]([NH:15][CH2:16][CH:17]1[CH2:19][CH2:18]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:20][C:21]1[CH:22]=[C:23]([N:27]=[C:28]=[O:29])[CH:24]=[CH:25][CH:26]=1>>[CH:17]1([CH2:16][NH:15][C:13](=[O:14])[CH2:12][N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3](=... | Cc1cccc(N=C=O)c1 | NCC(=O)N(CC(=O)NCC1CC1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The procedure is analogous to that described in Example 1, but 0.9 g of 2-(2-amino-N-phenylacetamido)-N-cyclopropylmethylacetamide and 0.45 g of 3-methylphenyl isocyanate are used as the starting material. After recrystallization from acetonitrile, 1 g of N-cyclopropylmethyl-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacet... | Cc1cccc(NC(=O)NCC(=O)N(CC(=O)NCC2CC2)c2ccccc2)c1 | null | 75 | null |
639,737 | ord_dataset-1c0bae7388cf460091d56129e95b3145 | null | 2004-01-01T00:06:00 | true | Br[C:2]1[CH:3]=[N:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=4)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[O:9])=[N:6][CH:7]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Sn](CCCC)(CCCC)CCCC.C(OCC)(=O)C.N>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC... | O=C(c1ncc(Br)cn1)N1CCN(S(=O)(=O)c2cc3cc(Cl)ccc3[nH]2)CC1 | CCCC[Sn](CCCC)(CCCC)c1ccccn1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 100 | 9 | At room temperature, 1-[(5-bromopyrimidin-2-yl)carbonyl]-4-[(5-chloroindol-2-yl)sulfonyl]piperazine (500 mg) and (pyridin-2-yl)tributyltin (418 mg) were dissolved in N,N-dimethylformamide (10 ml). To the reaction mixture was added tetrakis(triphenylphosphine)palladium(0) (69 mg), followed by stirring at 100° C. for 9 h... | O=C(c1ncc(-c2ccccn2)cn1)N1CCN(S(=O)(=O)c2cc3cc(Cl)ccc3[nH]2)CC1 | null | 51 | null |
80,166 | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | null | 1981-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[C:13]([C:16]2[NH:20][N:19]=[C:18]([Cl:21])[N:17]=2)=[C:12]([NH:22][C:23](=[O:33])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=2)[NH:11]1>COCCO.[Ni]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=... | O=C(Nc1[nH]n(-c2c(Cl)cc(Cl)cc2Cl)c(=O)c1-c1nc(Cl)n[nH]1)c1cccc([N+](=O)[O-])c1 | null | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCO | null | null | null | null | null | null | null | null | null | null | null | null | 26.4 g of Intermediate H were dissolved in 250 ml of methyl-cellosolve and reduced at 50° C. with H2 at 20 atmospheres and Ni Raney. After cooling, Ni was filtered and the solvent was evaporated under vacuum. The resulting solid was extracted with boiling ethanol and filtered, thus obtaining 18 g of a white solid melti... | Nc1cccc(C(=O)Nc2[nH]n(-c3c(Cl)cc(Cl)cc3Cl)c(=O)c2-c2nc(Cl)n[nH]2)c1 | null | 72.3 | null |
844,073 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([NH:12][C:13](=[O:17])[C:14]([OH:16])=O)=[CH:11][C:5]=2[O:4][CH2:3]1.[CH2:18]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)C>[O:16]=[C:14]([N:29]1[CH2:30][CH2:31][CH:26]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH... | c1ccc(CCC2CCNCC2)cc1 | O=C1COc2cc(NC(=O)C(=O)O)ccc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from N-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-oxalamic acid (Example 53b) and 4-phenethyl-piperidine [J. Amer. Chem. Soc., 72, 4953. (1950)] according to the method described in Example 1c. Melting Point: 128-132° C. (diethylether) | O=C1COc2cc(NC(=O)C(=O)N3CCC(CCc4ccccc4)CC3)ccc2N1 | null | null | null |
217,564 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | Cl.Cl.[F:3][C:4]([F:30])([F:29])[C:5]([NH:7][CH2:8][CH:9]1[CH2:14][N:13](CC2C=CC=CC=2)[CH2:12][CH2:11][N:10]1CC1C=CC=CC=1)=[O:6]>CO.[Pd].O>[F:29][C:4]([F:3])([F:30])[C:5]([NH:7][CH2:8][CH:9]1[CH2:14][NH:13][CH2:12][CH2:11][NH:10]1)=[O:6] | O=C(NCC1CN(Cc2ccccc2)CCN1Cc1ccccc1)C(F)(F)F | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | To a solution of 3.1 g (6.7 mmol) of 2-trifluoroacetylaminomethyl-1,4-diphenylmethyl piperazine dihydrochloride in 100 ml methanol was added a suspension of 0.5 g palladium on carbon in 2 ml water. The mixture was hydrogenized for 30 mn, the catalyst was filtered off and the solvent was removed, taken up in 10 ml absol... | O=C(NCC1CNCCN1)C(F)(F)F | null | 96.8 | null |
35,283 | ord_dataset-c8db783fb93842e89cdcd41afa59a141 | null | 1978-01-01T00:01:00 | true | ClC1C=CC=C(C(OO)=[O:9])C=1.C(Cl)(Cl)Cl.[CH3:16][S:17][CH:18]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:16][S:17]([CH:18]([C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:2... | CSC(c1ccc(Cl)cc1)c1ccc(Cl)cc1 | O=C(OO)c1cccc(Cl)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of 10.7 grams (0.0525 mole) of m-chloroperbenzoic acid in 150 ml. of chloroform was slowly added to a cool solution (5°-7° C.) of 14.1 grams (0.050 mole) of bis(p-chlorophenyl)methyl methyl sulfide in 500 ml. of chloroform, and the resulting solution stirred for two hours at a temperature of 5° C., while a w... | CS(=O)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1 | null | 78.2 | null |
194,359 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][N:13]([CH3:48])[C:14]([N:16]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:20]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[C:19]([CH3:37])[N:18]=[C:17]1SCC1C=CC(OC)=CC=1)=[O:15]>ClCCl.C(OCC)(=O)C>[CH3:48][N:13]([CH3:12])[C:14]([N:16]1[CH:21]([... | O=C(OO)c1cccc(Cl)c1 | COc1ccc(CSC2=NC(C)=C(C(=O)OC(C)C)C(c3cccc([N+](=O)[O-])c3)N2C(=O)N(C)C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 8 | 3-Chloroperoxybenzoic acid (3 eq, 2.5 mmol, 424 mg) was added to a solution of (+)-3,4-dihydro-3-[(dimethylamino)carbonyl]-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester in dry dichloromethane (8.2 ml) at 0° C. under a nitrogen atmosphere. The reaction was ... | CC1=C(C(=O)OC(C)C)C(c2cccc([N+](=O)[O-])c2)N(C(=O)N(C)C)C(=O)N1 | null | null | null |
1,273,302 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | C(OC(=O)[N:7]([C@H:10]1[C@H:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[CH2:13][N:12]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:27][CH2:26]2)=[O:24])[CH2:11]1)[CH2:8][CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:22][C:17]1[CH:16]=[C:15]([C@H:14]2[C@H:10]([NH:7][CH... | CCN(C(=O)OC(C)(C)C)[C@@H]1CN(C(=O)N2CCN(S(C)(=O)=O)CC2)C[C@H]1c1ccc(Cl)c(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | To a solution of rac-[(3S,4R)-4-(3,4-dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl ester (0.36 g, 0.66 mmol) in CH2Cl2 (10 ml) was added TFA (2 ml) at RT. Stirring was continued over night. The reaction mixture was then concentrated under vacuo, the crude d... | CCN[C@@H]1CN(C(=O)N2CCN(S(C)(=O)=O)CC2)C[C@H]1c1ccc(Cl)c(Cl)c1 | null | 84.3 | null |
605,339 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([CH2:17][CH3:18])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]([CH2:17][CH3:18])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1 | CCC1CN(Cc2ccccc2)CCC1=O | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 0.5 | Sodium borohydride (0.456 g, 12.0 mmole) was added to the stirred solution of 1-benzyl-3-ethyl piperidin-4-one (5.4 g, 24.0 mmole) in methanol (25 ml) at 0-5° C. over a period of 15 min, and stirring was continued for 30 min at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water... | CCC1CN(Cc2ccccc2)CCC1O | null | null | null |
1,418,073 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH2:1]([O:3][C:4](=[O:14])[C:5](=[N:12]O)[C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])[CH3:2].[ClH:15].[H][H]>C(O)C.[Pd]>[ClH:15].[CH2:1]([O:3][C:4](=[O:14])[CH:5]([NH2:12])[C:6](=[O:11])[C:7]([F:8])([F:9])[F:10])[CH3:2] | [H][H] | CCOC(=O)C(=NO)C(=O)C(F)(F)F | null | [Pd] | Cl | 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 stirred solution of 4,4,4-trifluoro-2-hydroxyimino-3-oxo-butyric acid ethyl ester (55 g, 0.258 mol) in ethanol (140 ml) was added with palladium on activated carbon and 4N hydrochloric acid (90 ml) accordingly. The reaction mixture was stirred in a Parr shaker under 0.3 MPa of hydrogen at room temperature for 2.5 hou... | CCOC(=O)C(N)C(=O)C(F)(F)F | null | 61.8 | null |
656,816 | ord_dataset-f5d908a6dcb44353a706166b5e9f7f88 | null | 2004-01-01T00:12:00 | true | [C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([O:23][CH:24]([CH2:35][N:36]=[N+]=[N-])[CH2:25][C:26]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[NH:28][CH:27]=4)[CH:22]=3)=[CH:14][CH:15]=2)[C:10]([CH3:39])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([... | Cc1nn(C(=O)OC(C)(C)C)c2ccc(-c3cncc(OC(CN=[N+]=[N-])Cc4c[nH]c5ccccc45)c3)cc12 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 4 | To a solution of Example 406A (480 mg) in ethanol was added 10% Pd/C (160 mg) under nitrogen. This suspension was purged with hydrogen (3 circles) and was stirred under hydrogen (balloon) for 4 h. The solid material was filtered off and the filtrate was concentrated to give the desired product (443 mg, 97%). MS (APCI) ... | Cc1nn(C(=O)OC(C)(C)C)c2ccc(-c3cncc(OC(CN)Cc4c[nH]c5ccccc45)c3)cc12 | null | 97.1 | null |
86,654 | ord_dataset-4a4f564f09ba483589e09e154ad32acf | null | 1981-01-01T00:10:00 | true | [OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]([CH3:21])[CH2:19][CH3:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Cl[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29].Cl>O.C(O)C>[OH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15... | OCCCCCCCl | CCC(C)COc1ccc(-c2ccc(O)cc2)cc1 | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | 4.5 g of KOH and 15 g of 4-hydroxy-4'-(2-methylbutoxy)-biphenyl are dissolved in 150 ml of a 1:1 water/ethanol mixture, the solution is raised to the boil and 9 g of 6-chloro-1-hexanol are slowly added dropwise, whilst stirring, after which the batch is refluxed for about 10 hours. When the reaction solution has cooled... | CCC(C)COc1ccc(-c2ccc(OCCCCCCO)cc2)cc1 | null | null | null |
796,504 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [I:1][C:2]1[CH:3]=[C:4]([N:8]2[S:12](=[O:14])(=[O:13])[NH:11][C:10](=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:35][O:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41]O)=[CH:39][CH:38]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([N:8]2[S:12](=[O:13])(=[O:14])[N:11]([CH2:41][C:4... | O=C1CN(c2cccc(I)c2)S(=O)(=O)N1 | COc1ccc(CO)cc1 | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.58 | The title B compound, 5-(3-iodo-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (932 mg, 2.76 mmol) is dissolved in tetrahydrofuran (20 mL) in a 40 mL capacity septum capped vial, stirred under argon balloon. Triphenylphosphine (1.47 g, 5.51 mmol) is added as a solid and stirred until dissolved, then 4-methyoxybenzyl alco... | COc1ccc(CN2C(=O)CN(c3cccc(I)c3)S2(=O)=O)cc1 | null | null | null |
202,373 | ord_dataset-19e5fc80c1554f4f8641c835e055f02b | null | 1990-01-01T00:01:00 | true | C(N[C@H:5]([C:13]([OH:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)C.[CH3:16][C:17]1[O:18]C(=O)C(=CC2C=CC=CC=2)[N:21]=1>O>[NH:21]([C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:6]=[CH:5][C:13]([OH:15])=[O:14])[C:17]([CH3:16])=[O:18] | CC1=NC(=Cc2ccccc2)C(=O)O1 | CC(=O)N[C@@H](Cc1ccccc1)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | In the process for the preparation of N-acetylphenylalanine by opening the ring of 2-methyl-4-benzylidene-1,3-oxazolin-5-one with water to give 2-acetaminocinnamic acid and subsequently catalytically hydrogenating the latter, both reaction stages are carried out in a mixture of an aliphatic C3 -ketone to C10 -ketone or... | CC(=O)Nc1ccccc1C=CC(=O)O | null | null | null |
341,930 | ord_dataset-4c84bc8a34e1469aa1b156355c91cdcc | null | 1996-01-01T00:10:00 | true | [C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([Sn](CCCC)(CCCC)COCC1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)CCC.C(OCC)C.[F-].[K+]>C(Cl)(Cl)Cl>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:9])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2... | CCCC[Sn](CCCC)(CCCC)COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | O=C(Cl)C(c1ccccc1)c1ccccc1 | null | [F-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 80 | null | Diphenylacetyl chloride (4.6 g), tri-n-butyl-((3,5-bis(trifluoromethyl)phenyl)methyloxymethyl)tin (12.6 g; Example 1a, (Method Ai)and benzylchlorobis(triphenylphosphine) palladium (II)(80 mg)were dissolved in chloroform (10 ml) and the solution heated at 80° C. for 6h. On cooling diethyl ether and saturated aqueous pot... | CC(=O)C(c1ccccc1)c1ccccc1 | null | null | null |
1,712,559 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([O:4][N:5]([C@@H:21]1[C:26]([C:27]([NH2:29])=[O:28])=[CH:25][C@@H:24]([CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[NH:23][CH2:22]1)S(C1C=CC([N+]([O-])=O)=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1>C1COCC1>[CH2:1]([O:4][NH:5][C@@H:21]1[C:26](... | C=CCON([C@H]1CN[C@H](CO[Si](C)(C)C(C)(C)C)C=C1C(N)=O)S(=O)(=O)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | O=C([O-])[O-] | Sc1ccccc1 | [Cs+] | 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 | To a reddish-brown, stirred suspension of (3R,6S)-3-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 106, 1.1 g, 1.9 mmol) and cesium carbonate (3.1 g, 9.5 mmol) in THF (about 45 mL), at ambient temperature under a blanket of argon... | C=CCON[C@H]1CN[C@H](CO[Si](C)(C)C(C)(C)C)C=C1C(N)=O | null | 78.6 | null |
1,700,273 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:28][C:29]1[CH:30]=[C:31]([C:44]([OH:47])([CH3:46])[CH3:45])[CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1>>[F:28][C:29]1[CH:... | CC(C)(O)c1cc(F)cc(B2OC(C)(C)C(C)(C)O2)c1 | O=C(Nc1ccc(OC(F)(F)F)cc1)c1cnc(N2CC[C@@H](O)C2)c(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in an analogous fashion to that described in Example 53 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and 2-(3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol and to afford a yellow resin. HPLC (Condition 4... | CC(C)(O)c1cc(F)cc(-c2cc(C(=O)Nc3ccc(OC(F)(F)F)cc3)cnc2N2CC[C@@H](O)C2)c1 | null | null | null |
1,717,982 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH:35]=O)[CH2:30][CH2:29]1)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:48]1([O:53][C:54](=[O:... | CC(C)C[C@H](N)C(=O)OC1CCCC1 | C=C(C)c1cc(C(=O)N2CCC(CC=O)CC2)c(OCc2ccccc2)cc1OCc1ccccc1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | Cc1ccc(S(=O)(=O)O)cc1 | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCCC | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of Intermediate D (0.245 g, 0.5 mmol) in dichloroethane (10 mL) was added L-leucine cyclopentyl ester tosylate (0.398 g, 1.07 mmol) and sodium triacetoxyborohydride (0.417 g, 1.97 mmol). The mixture was stirred for one hour then loaded directly onto a silica gel column and eluted with 7:3 ethyl acetate:he... | C=C(C)c1cc(C(=O)N2CCC(CCN[C@@H](CC(C)C)C(=O)OC3CCCC3)CC2)c(OCc2ccccc2)cc1OCc1ccccc1 | null | 75 | null |
1,550,013 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Cl.[NH2:2][C@H:3]([C@@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6]1)[CH3:4].C([O:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[CH:37][C:36]([CH2:39][N:40]2[C:48]3[C:43](=[CH:44][C:45]([C:49](O)=[O:50])=[CH:46][CH:47]=3)[C:42]([CH3:... | Cc1c(C)n(Cc2ccc(-c3ccccc3C(=O)OC(C)(C)C)cc2)c2ccc(C(=O)O)cc12 | C[C@H](N)[C@@H]1CCN(C(=O)OCc2ccccc2)C1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared following the same general protocol as described in Step 8-9, Example 1, using the (R)-benzyl 3-((S)-1-aminoethyl)pyrrolidine-1-carboxylate hydrochloride and the 1-((2′-(tert-butoxycarbonyl)-[1,1′-biphenyl]-4-yl)methyl)-2,3-dimethyl-1H-indole-5-carboxylic acid. ESI-MS (m/z): 630 [M+H]+. | Cc1c(C)n(Cc2ccc(-c3ccccc3C(=O)O)cc2)c2ccc(C(=O)N[C@@H](C)[C@@H]3CCN(C(=O)OCc4ccccc4)C3)cc12 | null | null | null |
1,441,667 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [N:1]1[N:2]2[CH2:13][CH2:12][CH2:11][C:3]2=[CH:4][C:5]=1[C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>O1CCOCC1>[N:1]1[N:2]2[CH2:13][CH2:12][CH2:11][C:3]2=[CH:4][C:5]=1[C:6]([OH:8])=[O:7] | CCOC(=O)c1cc2n(n1)CCC2 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 65 | null | A 25-mL round-bottomed flask equipped with a reflux condenser was charged with ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate (540 mg, 3.0 mmol), 2N Aqueous sodium hydroxide solution (3.5 mL), and 1,4-dioxane (3.0 mL). The system was heated at 65° C. for 2.5 h. It was then cooled to room temperature and adju... | O=C(O)c1cc2n(n1)CCC2 | null | 57 | null |
1,766,299 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=O)=[CH:15][CH:14]=2)=[CH:11][CH:10]=[N:9]1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]C#N)=[CH:25][CH:24]=1>>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:21][N:19]=[C:16]3[CH:15]=[CH:14][C:13]([C:12]4[N:8]([C:3]5[CH... | O=[N+]([O-])c1ccc(-c2ccnn2-c2ccccc2F)cc1 | N#CCc1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, light yellow solid (108 mg, 71%), MS (ISP) m/z=434.2 [(M+H)+], mp 202° C., was prepared in accordance with the general method of example 1 from 1-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole (intermediate B) (100 mg, 353 μmol) and commercially available 2-(4-bromo-phenyl)-acetonitrile. | Fc1ccccc1-n1nccc1-c1ccc2noc(-c3ccc(Br)cc3)c2c1 | null | null | null |
821,034 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | C1(=O)[N:5]([CH:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)C(=O)C2=CC=CC=C12.NN>C(O)C>[NH2:5][CH:6]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N... | O=C1c2ccccc2C(=O)N1CCCCCCCCCC(c1ccccn1)N1C(=O)c2ccccc2C1=O | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | 1,10-diphthalimido-1-pyridinyldecane (1 equiv.) and hydrazine (2 equiv.) are stirred in ethanol at reflux. The reaction mixture is cooled to room temperature and the resulting solid is filtered off. The filtrate is purified by silica gel chromatography to yield 1,10-diamino-1-pyridinyldecane. | NCCCCCCCCCC(N)c1ccccn1 | null | null | null |
827,188 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | [F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([O:15][C:16]3[C:21]4[N:22]=[C:23]([NH2:25])[S:24][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH:12]=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([O:15][C:... | Nc1nc2c(Oc3cncc(-c4ccc(C(F)(F)F)cc4)c3)cccc2s1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-[5-(4-trifluoromethyl-phenyl)-pyridin-3-yloxy]-benzothiazol-2-ylamine (12 mg, 0.031 mmol), acetic anhydride (10 uL, 0.074 mmol) and pyridine (1 mL) was heated at 60° C. for 18 h. The solution was concentrated under an N2 stream and the resulting mixture was purified by prep LC (10-90% CH3CN/H2O modified... | CC(=O)Nc1nc2c(Oc3cncc(-c4ccc(C(F)(F)F)cc4)c3)cccc2s1 | null | null | null |
61,525 | ord_dataset-912d62c1690b4ebfbe998c0c9baf88a8 | null | 1979-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:15][CH3:16])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].[CH2:19]=O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([N:15]([CH3:19])[CH3:16])[CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1 | CNC1(c2ccc(Cl)cc2)CCC(=O)CC1 | C=O | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A reaction solution consisting of 5.68 gm. (0.0201 mole) 4-(p-chlorophenyl)-4-methylaminocyclohexanone, ethylene ketal (prepared in Part G, above), 22 ml. 37 percent formalin (aqueous formaldehyde), and 75 ml. methanol is heated at the reflux temperature for four (4) hours, after which heating the solution is allowed t... | CN(C)C1(c2ccc(Cl)cc2)CCC(=O)CC1 | null | 59 | null |
218,274 | ord_dataset-640d007e35e243a286c8b7dd2b77ac1b | null | 1990-01-01T00:11:00 | true | [CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].[O:15]([C:22](OC1C=CC=CC=1)=[CH:23][N+:24]([O-:26])=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:22]([O:15][C:16]2[CH:21]=[CH:2... | CN(C)Cc1ccc(CSCCN)o1 | O=[N+]([O-])C=C(Oc1ccccc1)Oc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2·14 g (10 mmol) of 2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamine and 2·57 g (10 mmol) of 1,1-diphenoxy-2-nitroethene in 20 ml of acetonitrile is boiled for 2 hours. After concentration of the solution by evaporation under vacuum, the oily residue is chromatographically purified as descr... | CN(C)Cc1ccc(CSCCNC(=C[N+](=O)[O-])Oc2ccccc2)o1 | null | 81 | null |
1,761,885 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | Br[C:2]1C=CC(C(OC)=O)=C(C)C=1.[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=1[I:23]>>[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([O:20][CH3:2])=[O:19])=[CH:16][C:15]=1[I:23] | COC(=O)c1ccc(Br)cc1C | O=C(O)c1ccc(F)c(I)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 6.1, except 4-fluoro-3-iodobenzoic acid was used in place of 4-bromo-2-methylbenzoic acid. | COC(=O)c1ccc(F)c(I)c1 | null | null | null |
329,523 | ord_dataset-2c460e2ef9934444aaf26fec1f75741f | null | 1996-01-01T00:05:00 | true | [CH3:1][C:2]1([CH3:18])[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C([BH3-])#N.[Na+].O>C(O)(=O)C>[CH3:1][C:2]1([CH3:18])[C@H:17]2[C@H:9]([NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=32)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2 | CC1(C)c2ccccc2-c2[nH]c3ccccc3c21 | null | null | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 0.5 | 5,10-Dihydro-10,10-dimethylindeno [1,2-b]indole (1.00 g, 4.29 mmol) was reacted with sodium cyanoborohydride (1.0 g, 16 mmol) in glacial acetic acid (20 cm3), for 10 minutes. The solution was poured into water, stirred for 30 minutes, and extracted into diethylether. The organic phase was washed 10 times with water, dr... | CC1(C)c2ccccc2[C@H]2Nc3ccccc3[C@H]21 | null | null | null |
818,905 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [N:1]1([C:7]2[N:12]=[C:11]([OH:13])[CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O.O>O1CCOCC1>[C:18]([O:17][C:15]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:13])[N:12]=2)[CH2:6][CH2:5]1)=[O:14])([CH3:21])([CH3:20])[... | Oc1cccc(N2CCNCC2)n1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 75 | null | To a stirring solution of 6-piperazin-1-yl-pyridin-2-ol (0.6 g, 3.30 mmol—Pavia, M. R., Taylor, C. P., Hershenson, F. M., Lobbestael, S. J. J. Med. Chem. 1987, 30(7), 1210) in 1,4-dioxane (15 ml) was added t-BOC2O (0.80 g, 3.68 mmol) and H2O (3 ml). The reaction mixture was heated at 75° C. for 8 h and cooled to RT. Th... | CC(C)(C)OC(=O)N1CCN(c2cccc(O)n2)CC1 | null | null | null |
845,161 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]2[O:9][CH:8]([CH2:10][OH:11])[CH2:7][C:6]=2[CH:12]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>CN(C)C1C=CN=CC=1>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:11][CH2:10][CH:8]2[CH... | Cc1ccc(S(=O)(=O)Cl)cc1 | OCC1Cc2cc(Cl)cc(C3CCCCC3)c2O1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | Treatment of (±)-(5-chloro-7-cyclohexyl-2,3-dihydro-1-benzofuran-2-yl)methanol (4.5 g, 0.017 mol) with p-toluenesulfonyl chloride (4.8 g, 0.025 mol), diisopropylethylamine (4.36 g, 0.034 mol), and 4-(dimethylamino)pyridine (0.12 g, 0.98 mmol) generally according to the procedure described for Intermediate 45 gave (±)-(... | Cc1ccc(S(=O)(=O)OCC2Cc3cc(Cl)cc(C4CCCCC4)c3O2)cc1 | null | null | null |
1,714,616 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | Br[C:2]1[CH:3]=[C:4]([F:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[NH3:12]>O>[F:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH2:12])[CH:3]=1)[NH:9][CH:8]=[CH:7]2 | Fc1cc(Br)c2[nH]ccc2c1 | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 155 | null | A mixture of 7-bromo-5-fluoro-indole (1 g), Cu (0.31 g), CuBr (0.64 g) and NH3 (30 ml of a 33% aqueous solution) was heated in an autoclave for 1.5 h at 155° C. The mixture was diluted with water and extracted with EtOAc. The organic phase was dried and the solvent removed to give 5-fluoro-7-amino-indole as an oil whic... | Nc1cc(F)cc2cc[nH]c12 | null | null | null |
1,095,214 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=O)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[NH:20][NH2:21].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl>ClCCl>[C:24]([O:23][C:19]([NH:20][NH:21][C:14]([C@H:10]1[CH2:11][CH2:12][CH2:... | CC(C)(C)OC(=O)NN | O=C(O)[C@H]1CCCN(C(=O)c2ccc(F)cc2)C1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 1-(4-fluoro-benzoyl)-(S)-piperidine-3-carboxylic acid (1.05 g, 4.17 mmol), tert-butyl carbazate (0.55 g, 4.17 mmol), HOBT (0.562 g, 4.17 mmol), EDCI.HCl (1.2 g, 6.25 mmol) in dry dichloromethane (8 mL) was kept under stirring overnight at ambient temperature, under nitrogen atmosphere. HCl 1N (30 mL) was t... | CC(C)(C)OC(=O)NNC(=O)[C@H]1CCCN(C(=O)c2ccc(F)cc2)C1 | null | 46.9 | null |
1,264,088 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1.[Cl:19][C:20]1[C:21]([C:30](O)=[O:31])=[N:22][N:23]([CH2:25][C:26]([F:29])([F:28])[F:27])[CH:24]=1>>[NH2:16][C:10]1[O:11][CH2:12][C:13]([F:14])([F:15])[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:30... | C[C@]1(c2cc(N)ccc2F)N=C(N)OCC1(F)F | O=C(O)c1nn(CC(F)(F)F)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 condensation of (R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate XI-1) and 4-chloro-1-(2,2,2-trifluoro-ethyl)-1H-pyrazole-3-carboxylic acid (CAS1006448-63-0) following procedure I yielded the title compound as a white solid. MS (ISP): m/z=470.2 [M+H]+. | C[C@]1(c2cc(NC(=O)c3nn(CC(F)(F)F)cc3Cl)ccc2F)N=C(N)OCC1(F)F | null | null | null |
1,264,740 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:10]([C:20]([OH:22])=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:10]([C:20]([OH:22])=[O:21])[CH2:9]1)=[O:7]... | CC(C)(C)OC(=O)N1CCC(c2ccccc2)=C(C(=O)O)C1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 2 | 1-(tert-Butoxycarbonyl)-4-phenyl-1,2,5,6-tetrahydropyridin-3-carboxylic acid (5.63 g) was dissolved in methanol (60 ml), and thereto was added palladium-carbon (4.06 g), and the mixture was stirred under hydrogen atmosphere for 2 hours. The reaction solution was filtered on celite, and concentrated under reduced pressu... | CC(C)(C)OC(=O)N1CC[C@H](c2ccccc2)[C@H](C(=O)O)C1 | null | 84 | null |
55,061 | ord_dataset-159c363342e44b539e7a5975c873e30d | null | 1979-01-01T00:05:00 | true | [C:1]([CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[CH2:10][C:11]([CH3:16])([CH3:15])[O:12]2)=[CH:7][CH:6]=1)#[N:2].[BrH:27]>[Pd].C(O)C>[BrH:27].[NH2:2][CH2:1][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([... | CC1(C)CC(c2cccc(C(F)(F)F)c2)c2ccc(OCC#N)cc2O1 | null | null | [Pd] | Br | 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 7-cyanomethyloxy-2,2-dimethyl-4-(3-trifluoromethylphenyl) chroman (5.4 g) and 10% palladium on charcoal (0.5 g) in ethanol (75 ml) was hydrogenated at atmospheric pressure. The catalyst was removed by filtration and the filtrate evaporated under reduced pressure to give an oil which was treated with ether... | CC1(C)CC(c2cccc(C(F)(F)F)c2)c2ccc(OCCN)cc2O1 | null | null | null |
1,583,727 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][N:5]([C:8]2[N:13]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:16]=[C:12]3[N:11]=[C:10]([CH3:23])[C:9]=2[CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:4][CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C2[O:48]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1.C1(C)C=CC=CC=1>[CH3:1... | COC(=O)Cc1c(C)nc2nc(-c3ccccc3)nn2c1N1CCC(C)(C)CC1 | O=S(=O)(c1ccccc1)N1OC1c1ccccc1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | -78 | 0.5 | To a solution of methyl 2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate (106 mg, 0.269 mmol) in anhydrous THF (5 ml) at −78° C. was added dropwise KHMDS (0.808 mL, 0.404 mmol) in toluene. Reaction mixture was stirred at −78° C. for 30 min and to this was added dropwise 3-... | COC(=O)C(O)c1c(C)nc2nc(-c3ccccc3)nn2c1N1CCC(C)(C)CC1 | null | 49.8 | null |
223,947 | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | null | 1991-01-01T00:02:00 | true | [Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[OH:7][CH:8]([CH3:41])[CH2:9][S:10]([C:13]1[CH:14]=[C:15]([C@H:24]2[CH2:28][CH2:27][C@H:26]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[O:25]2)[CH:16]=[C:17]([OH:23])[C:18]=1[O:19][CH2:20][CH2:21][CH3:22])(=[O:12])=[O:11].C(=O)([O-])[... | CCCOc1c(O)cc([C@H]2CC[C@H](c3cc(OC)c(OC)c(OC)c3)O2)cc1S(=O)(=O)CC(C)O | BrCCCCBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 70 | 1.5 | 1,4-Dibromobutane (75 uL, 0.63 mmol) was added to a solution of trans-2-[3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (75 mg, 0.15 mmol) in DMF (0.5 mL) containing potassium carbonate (75 mg, 0.54 mmol). The reaction mixture was heated with stirring under nitroge... | CCCOc1c(OCCCCBr)cc([C@H]2CC[C@H](c3cc(OC)c(OC)c(OC)c3)O2)cc1S(=O)(=O)CC(C)O | null | null | null |
908,424 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH2:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([S:14][C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)[C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3][NH:2]1.[CH2:22]=O.[BH4-].[Na+]>CO>[CH3:22][N:2]1[CH2:3][CH2:4][C:5]2[NH:6][C:7]3[C:8]([S:14][C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)=[CH:9][CH:10]=[CH:11][C:... | Cc1ccc(Sc2cccc3c4c([nH]c23)CCNC4)cc1 | C=O | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | 2 | 4-Methylphenyl 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl sulfide (200 mg, 0.68 mmol) was brought to reflux with formaldehyde (37% aq., 0.68 mL) in MeOH (1.8 mL) for 30 minutes. The reaction was then cooled to 0° C. and sodium borohydride (89 mg, 1.3 mmol) was added slowly. The solution was allowed to stir at room t... | Cc1ccc(Sc2cccc3c4c([nH]c23)CCN(C)C4)cc1 | null | 76 | null |
1,274,594 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [O:1]=[C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([C:19]([F:22])([F:21])[F:20])[CH:5]=[CH:4][NH:3]1.Br[CH2:24][C:25]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[N:27](C(OC(C)(C)C)=O)[N:26]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:1]=[C:2]1[C:7]([O:8][C:9]2[CH:10... | N#Cc1cc(C#N)cc(Oc2c(C(F)(F)F)cc[nH]c2=O)c1 | CC(C)(C)OC(=O)n1nc(CBr)c2cccnc21 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 16 | 5-{[2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl]oxy}isophthalonitrile (0.076 g, 0.249 mmol), tert-butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (0.078 g, 0.249 mmol) and potassium carbonate (0.034 g, 0.249 mmol) were combined and diluted with dimethylformamide (1 mL) and stirred at room temperatu... | N#Cc1cc(C#N)cc(Oc2c(C(F)(F)F)ccn(Cc3n[nH]c4ncccc34)c2=O)c1 | null | null | null |
310,602 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | [CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[NH:8][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].[N+:24]([O-])([OH:26])=[O:25].O>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[NH:8][C:9]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:10]... | CCOC(=O)c1cc(-c2ccccc2)[nH]c(=O)c1C(=O)OCC | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | -10 | 0.75 | In 13 ml of acetic anhydride was suspended 5.0 g of 3,4-diethoxycarbonyl-6-phenyl-2-pyridone; and the suspension was cooled to -10° C. Fuming nitric acid (1.32 ml; 2.0 eq.) was added dropwise over 1 hour, and the mixture was stirred for 45 minutes as it is. After 40 ml of water was added, the mixture was stirred at roo... | CCOC(=O)c1c([N+](=O)[O-])c(-c2ccccc2)[nH]c(=O)c1C(=O)OCC | null | null | null |
143,161 | ord_dataset-1895fe091c3f47afa1ee96a41a250de4 | null | 1986-01-01T00:05:00 | true | [CH3:1][CH:2]1[CH2:6][C:5]2[C:7]([Cl:15])=[C:8]([CH3:14])[CH:9]=[C:10]([N+:11]([O-])=O)[C:4]=2[O:3]1.[H][H]>C1COCC1.[Pd]>[NH2:11][C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[C:7]([Cl:15])=[C:8]([CH3:14])[CH:9]=1 | [H][H] | Cc1cc([N+](=O)[O-])c2c(c1Cl)CC(C)O2 | 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 | null | 51.0 g of 3C was dissolved in 600 ml of THF. The solution was divided in half, and each half was hydrogenated (40-50 psig hydrogen pressure) in the presence of 1 g of palladium-on-charcoal catalyst. The final combined reaction mixtures were filtered, the filtrates were combined, dried (MgSO4) and evaporated to dryness,... | Cc1cc(N)c2c(c1Cl)CC(C)O2 | null | null | null |
591,743 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [CH2:1]([O:3][C:4](=[O:10])[CH:5]([CH3:9])[CH2:6][CH2:7]Cl)[CH3:2].[NH2-].[Na+]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1([CH3:9])[CH2:7][CH2:6]1)=[O:10])[CH3:2] | CCOC(=O)C(C)CCCl | null | null | [NH2-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | Cannon and coworkers (J. Am. Chem. Soc., 1959, 81, pages 1660-1666) disclose the reaction of α-methyl-γ-chlorobutyric acid ethyl ester with sodamide under strictly anhydrous conditions in benzene to provide 1-methylcyclopropane carboxylic acid ethyl ester in a yield of 47.6%. Schwarze and coworkers, U.S. Pat. No. 4,520... | CCOC(=O)C1(C)CC1 | null | 47.6 | null |
1,129,282 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]1=[O:15].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:27][S:28]([O:14][CH2:13][C@@H:11]1[O:10][C:9](=[O:15])[N:8]([CH2:7][CH2:6][O:5][C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=2[O:2][C... | CS(=O)(=O)Cl | COc1ccccc1OCCN1C[C@H](CO)OC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | Using dichloromethane solution of the compound of formula 2 prepared in Example 2 80.1 g (0.3 mol), triethylamine 45.5 g (0.45 mol) and methanesulfonyl chloride 37.8 g (0.33 mol), the procedures as described in Example 7 were carried out to obtain the targeted product. | COc1ccccc1OCCN1C[C@H](COS(C)(=O)=O)OC1=O | null | null | null |
880,423 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C@@H:9]([NH2:17])[C@H:8]([O:18][CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:7]=1)=[O:5])[CH3:2].C(=O)([O-])O.[Na+].[C:29](OC(=O)C)(=[O:31])[CH3:30]>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:... | CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N)[C@H](OS(C)(=O)=O)C1 | CC(=O)OC(C)=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 | 1 | To a solution of 190 mg of 20 and EtOAc (1.6 mL) in a 10 mL round-bottom flask equipped with a magnetic stirrer and an inert gas supply was added was added at RT aqueous 1 M sodium hydrogen carbonate (1.6 mL). To the resulting mixture was added 62 μl of acetic anhydride and the 2-phase mixture was stirred for 1 h at RT... | CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@H](OS(C)(=O)=O)C1 | null | null | null |
606,415 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9](=[O:11])[CH2:10][C:3]=12.[N:12]1([CH2:18][CH2:19][NH:20][C:21]([C:23]2[NH:24][C:25]([CH:29]=O)=[C:26]([CH3:28])[CH:27]=2)=[O:22])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.N1CCCCC1>C(O)C>[N:12]1([CH2:18][CH2:19][NH:20][C:21]([C:23]2[NH:24][C:25]([CH:29]=[C:10]3[C:3]4[C:4](=... | O=C1Cc2c(Cl)ccnc2N1 | Cc1cc(C(=O)NCCN2CCOCC2)[nH]c1C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | CCO | null | null | null | null | null | null | null | null | null | 25 | 8 | A reaction mixture of 4-chloro-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (85 mg, 0.5 mmol), 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide (125 mg, 0.5 mmol), 0.1 mL of piperidine and 10 mL of ethanol was stirred at room temperature overnight. The yellow precipitate was filtered after coole... | Cc1cc(C(=O)NCCN2CCOCC2)[nH]c1C=C1C(=O)Nc2nccc(Cl)c21 | null | 89 | null |
1,740,890 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[C:16]3[N:17]=[CH:18][N:19]=[C:20]([C:21]4[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=4[O:29][CH2:30][CH:31]4[CH2:33][CH2:32]4)[C:15]=3[NH:14][C:13]=2[CH3:34])=[O:11])[CH2:5][CH2:4]1.[C:35](Cl)(=[O:37])[CH3:36]>>[C:35]([NH:2][C@H:3]1[CH2:8][CH2:7][C@H:... | CC(=O)Cl | COc1ccc(OCC2CC2)c(-c2ncnc3c(C(=O)N[C@H]4CC[C@H](N)CC4)c(C)[nH]c23)c1 | 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 N-(trans-4-aminocyclohexyl)-4-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide hydrochloride (example D.f24) and commercially available acetyl chloride the title compound is obtained as colorless solid. | COc1ccc(OCC2CC2)c(-c2ncnc3c(C(=O)N[C@H]4CC[C@H](NC(C)=O)CC4)c(C)[nH]c23)c1 | null | null | null |
1,049,892 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH3:9][NH:10][CH3:11]>C(O)C>[Br:1][C:2]1[N:3]=[C:4]([N:10]([CH3:11])[CH3:9])[CH:5]=[CH:6][CH:7]=1 | Brc1cccc(Br)n1 | CNC | 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 | Heat a stirred mixture of 2,6-dibromopyridine (15; g, 63; mmol) and dimethylamine (40% aqueous solution, 21.4; mL, 190; mmol, 3; equiv) in ethanol (75; mL) for 3; days at 70° C. Evaporate the yellow solution to a reduced volume and dilute with ethyl acetate (100; mL). Wash with water (40; mL), brine (40; mL) and dry ov... | CN(C)c1cccc(Br)n1 | null | null | null |
1,146,752 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [F:1][C:2]([F:16])([F:15])[S:3]([O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:18].[K+].[K+]>S(=O)(=O)(O)O>[F:16][C:2]([F:15])([F:1])[S:3]([O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]([OH:18])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:5] | O=Cc1ccc(OS(=O)(=O)C(F)(F)F)cc1 | O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-] | null | O=S(=O)(O)O | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 65 | null | A suspension of 4-(trifluoromethanesulfonyloxy)benzaldehyde (5.2 g, 20.5 mmol, described in JACS, 1987, 109, 5478) and potassium dichromate (2.5 g) in sulfuric acid (30%, 47 mL) was heated at 65° C. for 1 h. The mixture was allowed to cool to ambient temperature and then poured on ice. The formed precipitate was filter... | O=C(O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1 | null | 114.5 | null |
696,500 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [Br:1][C:2]1[N:3]=[C:4]([CH2:21][CH3:22])[C:5]([NH:10][C@@H:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17]C=3)[CH2:13][C@@H:12]2O)=[N:6][C:7]=1[CH2:8][CH3:9].C(C1C(NC2C3=NC=CC=C3CC2)=[N:27]C(CC)=CN=1)C>>[Br:1][C:2]1[N:3]=[C:4]([CH2:21][CH3:22])[C:5]([NH:10][CH:11]2[C:19]3=[N:27][CH:17]=[CH:16][CH:15]=[C:14]3[CH2:13][CH2:12]... | CCc1cnc(CC)c(NC2CCc3cccnc32)n1 | CCc1nc(N[C@@H]2c3ccccc3C[C@@H]2O)c(CC)nc1Br | null | null | null | null | null | null | null | 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 the preparation of (1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol but substituting N-(3,6-diethylpyrazin-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine and making non-critical variations provided the title compound as a oil: 1H NMR (300 MHz, CDCl3) δ) 8.47, 7... | CCc1nc(NC2CCc3cccnc32)c(CC)nc1Br | null | null | null |
1,043,420 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[CH:2].Br[C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=1)[C:16]#[N:17]>>[NH2:6][C:5]1[CH:4]=[C:3]([C:1]#[C:2][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:9]=[CH:8][CH:7]=1 | C#Cc1cccc(N)c1 | N#Cc1cncc(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepare according to the general procedure outlined in EXAMPLE 30 using 3-ethynylaniline (1.0 g, 8.5 mmol) and 5-bromonicotinonitrile (1.56 g, 8.54 mmol) to give the title compound (0.7 g, 38%). | N#Cc1cncc(C#Cc2cccc(N)c2)c1 | null | 37.6 | null |
951,413 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | C(N([P:6](N(CC)CC)[C:7]1[N:12]=[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=[CH:9][CH:8]=1)CC)C.[CH:25]1[CH:30]=[C:29]2[CH:31]=[CH:32][C:33]([OH:46])=[C:34]([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][C:36]=3[OH:45])[C:28]2=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[CH:38]1[C:... | CCN(CC)P(c1cccc(NC(=O)C(C)(C)C)n1)N(CC)CC | Oc1ccc2ccccc2c1-c1c(O)ccc2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | N-(6-(bis(diethylamino)phosphino)pyridin-2-yl)pivalamide (0.292 g, 0.60 mmol, 1 eq) was dissolved in toluene (12 ml). (S)-BINOL (0.172 g, 0.60 mmol, 1 eq) was subsequently added and the reaction mixture was refluxed for 3 hours. The solvent was removed under reduced pressure. The title compound could be obtained in the... | CC(C)(C)C(=O)Nc1cccc(-p2oc3ccc4ccccc4c3c3c(ccc4ccccc43)o2)n1 | null | null | null |
1,012,415 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:15]([O:19][C:20]([C:22]1[CH:32]=[C:31]([OH:33])[C:25]2[CH2:26][CH:27]([CH2:29][OH:30])[O:28][C:24]=2[CH:23]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[C:15]([O:19][C:20]([C:22]1[CH:32]=[C:31]([O:33][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=... | CC(C)(C)OC(=O)c1cc(O)c2c(c1)OC(CO)C2 | BrCc1ccccc1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Benzyl bromide (1.8 mL, 15.2 mmol) and Cs2CO3 (4.89 g, 15.0 mmol) were added to a solution of 4-hydroxy-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (200f) (4.0 g, 15.0 mmol) in DMF (10 mL). The reaction mixture was stirred at room temperature overnight. The mixture was quenched with H2O (6... | CC(C)(C)OC(=O)c1cc(OCc2ccccc2)c2c(c1)OC(CO)C2 | null | 82.9 | null |
1,553,326 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Cl[C:11]1[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]3)=[C:21]([O:31][CH3:32])[CH:20]=2)[N:12]=1>>[CH3:32][O:31][C:21]1[CH:20]=[C:19]([NH:18][C:13]2[N:12]=[C:11]([O:1][C:2]3[CH:3]=[C:4](... | N#Cc1cccc(O)c1 | COc1cc(Nc2nc(C)cc(Cl)n2)ccc1-n1cnc(C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in analogous manners as described in example 9) from 3-hydroxy-benzonitrile and (4-chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine. It was obtained in 75% yield as a pale-brown solid. MS ISP (m/e): 413.4 (100) [(M+H)+]. | COc1cc(Nc2nc(C)cc(Oc3cccc(C#N)c3)n2)ccc1-n1cnc(C)c1 | null | 75 | null |
73,081 | ord_dataset-10f2568b472a4cabb35c3f313a159005 | null | 1980-01-01T00:11:00 | true | [NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[O:10][C:9]([CH2:11][N:12]([OH:14])[CH3:13])=[CH:8][CH:7]=1.CS[CH:17](SC)[CH2:18][N+:19]([O-:21])=[O:20]>>[OH:14][N:12]([CH2:11][C:9]1[O:10][C:6]([CH2:5][S:4][CH2:3][CH2:2][NH:1][C:17]([NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]2[O:10][C:9]([CH2:11][N:12]([OH:14])[CH3:13])=[CH:8][CH:7]=... | CSC(C[N+](=O)[O-])SC | CN(O)Cc1ccc(CSCCN)o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-[[(2-aminoethyl)thio]methyl]-N-hydroxy-N-methyl-2-furanmethanamine base (1.48 g) and 1,1-bis-(methylthio)-2-nitroethane (0.57 g) was heated at 98°-100° for 3 hr. The oily residue was chromatographed (silica/acetone) and the appropriate eluate evaporated to give the title compound (0.78 g) as an amber oil... | CN(O)Cc1ccc(CSCCNC(=C[N+](=O)[O-])NCCSCc2ccc(CN(C)O)o2)o1 | null | 45.6 | null |
117,740 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | [Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].CC[O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:18]([O:17][C:15]([C:14]1[C:13](=[O:12])[C:7]2[C:5](=[CH:4][C:3]([Cl:9])=[C:2]([Br:1])[CH:8]=2)[NH:6][CH:20]=1)=[O:16])[CH3:19] | Nc1ccc(Br)c(Cl)c1 | CCOC=C(C(=O)OCC)C(=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccc(Oc2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4-bromo-3-chloroaniline (8.3 g) and diethyl ethoxymethylene malonate (8.9 g) was heated at 120°-130° C. for 1.5 hours. The mixture was added to diphenyl ether (140 ml) and refluxed for 30 minutes. The cooled mixture was filtered, the solid was washed with benzene and dried. The solid was recrystallized fro... | CCOC(=O)c1c[nH]c2cc(Cl)c(Br)cc2c1=O | null | 88 | null |
1,404,895 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)O)([CH3:4])([CH3:3])[CH3:2].[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7... | O=C1NC(=O)c2ccccc21 | CC(C)(C)OC(=O)NCCC(O)c1cccc(Cl)c1 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1 | To a stirred solution of [3-(3-chloro-phenyl)-3-hydroxy-propyl]carbamic acid tert-butyl ester (12 g, 42 mmol), phthalimide (6.2 g, 42 mmol), and PPh3 (14.3 g, 55 mmol) in THF (150 mL) was added DEAD (9.0 mL, 55 mmol) dropwise at about 5° C. After 1 hour, the mixture was concentrated to dryness. The residue was purified... | CC(C)(C)OC(=O)NCCC(c1cccc(Cl)c1)N1C(=O)c2ccccc2C1=O | null | null | null |
623,786 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [OH-].[Na+].[CH:3]1[C:13]2[C:12](=[CH:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=3)[C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]=3[CH2:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)C>[CH:3]1[C:13]2[C:12](=[CH:14][CH2:15][CH2:16][O:17][C:1... | CCOC(=O)C(Cc1ccc(OCCC=C2c3ccccc3COc3ccccc32)cc1)OCC | null | null | [Na+] | [OH-] | 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 | 78 | Sodium hydroxide (1M, 2.5 ml, 2.5 mmol) was added to a solution of a 4:1 E/Z double-bond isomer mixture of ethyl 3-{4-[3-(6H-dibenzo[b,e]oxepin-11-ylidene)-propoxy]-phenyl}-2-ethoxy-propionate (0.24 g, 0.51 mmol) in ethanol (5 ml) and the mixture stirred at room temperature for 78 h. The resulting mixture was partition... | CCOC(Cc1ccc(OCCC=C2c3ccccc3COc3ccccc32)cc1)C(=O)O | null | null | null |
501,483 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [C:1]([O:4][CH:5]1[O:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:9][C:10](=[O:12])[CH3:11])[C@H:6]1[NH2:7])(=[O:3])[CH3:2].[I:25][C:26]1[CH:31]=[C:30]([I:32])[CH:29]=[C:28]([I:33])[C:27]=1[C:34]1[CH:39]=[CH:38][C:37]([C:40](Cl)=[O:41])=[C:36]([N+:43]([O-:45])=[O:... | O=C(Cl)c1ccc(-c2c(I)cc(I)cc2I)cc1[N+](=O)[O-] | CC(=O)OC[C@H]1OC(OC(C)=O)[C@H](N)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1,3,4,6-tetra-O-acetyl-D-glucosamine (9) is reacted with 2′,4′,6′-triiodo-3-nitrobiphenyl-4-carbonyl chloride (7) to yield 2-nitro-4-(2′,4′,6′-triiodophenyl)-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (10). | CC(=O)OC[C@H]1OC(OC(C)=O)(C(=O)c2ccc(-c3c(I)cc(I)cc3I)cc2[N+](=O)[O-])[C@H](N)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | null |
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