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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
575,328 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | Br[C:2]1[C:3]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:4][N:5]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:6]=12.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)... | N#Cc1ccc2c(Br)c(-c3ccc(F)cc3)nn2c1 | CS(=O)(=O)c1ccc(B(O)O)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=P([O-])([O-])[O-] | [K+] | 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 | null | null | To a solution of 3-bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carbonitrile (0.24 g 0.76 mmol) in DMF (20 ml) was added 4-methanesulfonylphenylboronic acid (0.202 g 1.1 mmol), ground potassium phosphate (0.45 g 20 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.03 g) and the mixture heated to 90° for 6 h un... | CS(=O)(=O)c1ccc(-c2c(-c3ccc(F)cc3)nn3cc(C#N)ccc23)cc1 | null | 6.4 | null |
477,374 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>>[O:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][NH:10][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:14][CH2:15]1 | NCCN1CCOCC1 | N#Cc1ccccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | According to a similar manner to that in Reference Example 3, the title compound was synthesized from 2-fluorobenzonitrile and 4-(2-aminoethyl)morpholine. | N#Cc1ccccc1NCCN1CCOCC1 | null | null | null |
1,612,037 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.Br[C:37]1[CH:38]=[N:39][N:40]([C@@H:42]2[CH2:46][CH2:45][O:44][CH2:43]2)[CH:41]=1>>[OH:1][C:2]([CH3:... | C[C@@H](c1ccc(B2OC(C)(C)C(C)(C)O2)cc1)N1CC[C@](CC(C)(C)O)(c2ccccc2)OC1=O | Brc1cnn([C@@H]2CCOC2)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 from (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-{(S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-ethyl}-1,3-oxazinan-2-one and 4-bromo-1-[(R)-tetrahydro-furan-3-yl]-1H-pyrazole following a procedure analogous to that described in Example 1. Yield: 31% of theory; LC (method... | C[C@@H](c1ccc(-c2cnn([C@@H]3CCOC3)c2)cc1)N1CC[C@](CC(C)(C)O)(c2ccccc2)OC1=O | null | 31 | null |
1,206,544 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH2:16][NH:17][CH:18]3[CH2:23][CH2:22][CH:21]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]3)[CH:9]=2)=[CH:4][CH:3]=1.[Cl:33][C:34]1[C:35]2[CH:45]=[CH:44][CH:43]=[CH:42][C:36]=2[S:37][C:38]=1[C:... | O=C(Cl)c1sc2ccccc2c1Cl | COc1ccc(-c2ccc(Cl)cc2)cc1CNC1CCC(N(C)C(=O)OC(C)(C)C)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 | Biaryl amine 34 (348 mg, 0.76 mmol) is treated with 3-chloro-benzo[b]thiophene-2-carbonyl chloride (210 mg, 0.91 mmol) using Method D to give the title compound. | COc1ccc(-c2ccc(Cl)cc2)cc1CN(C(=O)c1sc2ccccc2c1Cl)C1CCC(N(C)C(=O)OC(C)(C)C)CC1 | null | null | null |
208,041 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | Cl.[NH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]([OH:10])=[O:9].S(Cl)(Cl)=O.[CH3:15]O>>[NH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]([O:10][CH3:15])=[O:9] | CO | O=C(O)C1COCCN1 | null | Cl | 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 | -20 | 16 | Morpholine-3-carboxylic acid hydrochloride (1.04 g) was dissolved in methanol (20 ml) and the solution cooled to -20° C. Thionyl chloride (1 ml) was added dropwise to the stirred reaction mixture such that the temperature did not rise above -10°. After the addition was complete the reaction mixture was stirred at room ... | COC(=O)C1COCCN1 | null | null | null |
1,361,180 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[NH:20][C:12]3=[N:13][CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=[C:11]3[CH:10]=2)=[O:8])[CH2:3][CH2:2]1.[H][H]>[Pd].CO>[NH2:17][C:15]1[CH:16]=[C:11]2[CH:10]=[C:9]([C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[O:8])[NH:20][C:12]2=[N:13][CH:14]=1 | O=C(c1cc2cc([N+](=O)[O-])cnc2[nH]1)N1CCOCC1 | [H][H] | 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 | 18 | An autoclave is charged with 313 mg (1.13 mmol) of the morpholino(5-nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)methanone formed during the preceding stage, 100 mL of methanol and 31 mg of palladium on charcoal at 10%. The autoclave is placed under 20 bar of hydrogen and the solution is stirred at room temperature for 18 hours... | Nc1cnc2[nH]c(C(=O)N3CCOCC3)cc2c1 | null | null | null |
1,769,402 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | Cl[CH2:2][C:3]1[C:4]([S:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:16][C:17](=[O:29])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([OH:27])=[C:22]([F:28])[CH:21]=1)C>>[F:26][C:24]1[CH:25]=[C:20]([CH2:19][CH2:18][C:17]([OH:29])=[O:16])[CH:21]=[C:22]([F:28])[C:23]=1[O:27][CH2:2][C:3]1[C:4]... | CCOC(=O)CCc1cc(F)c(O)c(F)c1 | CC(C)CSc1ncccc1CCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-Chloromethyl-2-isobutylsulfanyl-pyridine (0.048 g, 0.22 mmol) obtained in Step C of Preparation Example 12 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (0.051 g, 0.22 mmol) obtained in Step D of Preparation Example 2 were used to react sequentially in the same manner as in Steps A and B of Example... | CC(C)CSc1ncccc1COc1c(F)cc(CCC(=O)O)cc1F | null | 60 | null |
1,116,872 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1 | COC(=O)c1ccc(C(O)CC(C)C)cc1 | null | null | O=[Cr](=O)([O-])Cl | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 4-(1-hydroxy-3-methyl-butyl)-benzoic acid methyl ester (19.72 g, 88.78 mmol) in dichloromethane (300 mL) is added pyridinium chlorochromate (22.03 g, 97.65 mmol). The mixture is allowed to stir at room temperature, and the solution turns black over time. The reaction is monitored by HPLC. Upon complete... | COC(=O)c1ccc(C(=O)CC(C)C)cc1 | null | 80.7 | null |
1,316,662 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[CH:22]=1)=[O:19])C1C=CC=CC=1>[Pd].CO>[OH:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28]... | COc1cc(NC(=O)[C@@H]2CC[C@@H]3CN2C(=O)N3OCc2ccccc2)ccn1 | 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 | 8 | Palladium on carbon (13.4 mg; 10% Pd/C) was added to a solution of (2S,5R)-6-(benzyloxy)-N-(2-methoxypyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (43.6 mg, 0.114 mmol) in methanol (1 mL) and the resulting mixture was stirred under hydrogen (balloon) overnight. HPLC analysis showed reaction complete. ... | COc1cc(NC(=O)[C@@H]2CC[C@@H]3CN2C(=O)N3O)ccn1 | null | null | null |
690,069 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | [Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]2[N:27]([CH3:28])[N:26]=[C:25]([O:29][CH2:30][CH2:31][OH:32])[C:24]=2[C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>>[Br:1][C:2]1[CH:3]=[N:4][C:5... | Clc1ncc(Br)cn1 | Cn1nc(OCCO)c(-c2ccc(Cl)cc2)c1NS(=O)(=O)c1ccc(C(C)(C)C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was made according to the procedure used for Example 13 except that (21 mg) of 5-bromo-2-chloropyrimidine was used and 4-(tert-butyl)-N-[4-(4-chlorophenyl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl]benzenesulfonamide (Example 19) (30 mg) was used in place of 4-(tert-butyl)-N-{3-(2-hydroxyethoxy)-1... | Cn1nc(OCCOc2ncc(Br)cn2)c(-c2ccc(Cl)cc2)c1NS(=O)(=O)c1ccc(C(C)(C)C)cc1 | null | null | null |
1,394,911 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[C:9]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)[CH:10]=1)=[O:4]>[Pd].C(O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:17][CH2:18][C:19]([F:22])([F:20])[F:21])=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:10]=1... | COC(=O)c1cnc(OCC(F)(F)F)c(C2=CCCCC2)c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 1.5 | 5-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid methyl ester (163 mg, 517 μmol) was combined with ethanol (5 mL) to give a colorless solution. Palladium (10% on charcoal, 16.3 mg, 517 μmol) was added and the suspension was evacuated and flushed with hydrogen 3 times and stirred for 1.5 h at ambien... | COC(=O)c1cnc(OCC(F)(F)F)c(C2CCCCC2)c1 | null | 57.9 | null |
1,321,889 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH2:1]([OH:22])[CH2:2][CH:3]([OH:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH3:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([C:29](Cl)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:3... | CCCCCCCCCCCCCCCCCC(O)CCO | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)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 | 16 | Icosane-1,3-diol (3.7 g, 11.8 mmoles) is co-evaporated twice with anhydrous pyridine (50 mL each) and then is dissolved in anhydrous pyridine (60 mL). The solution is chilled in an ice bath, and 4,4′-dimethoxytritylchloride (4.2 g, 12.4 mmoles) is added. The reaction is allowed to warm to ambient temperature and is sti... | CCCCCCCCCCCCCCCCCC(O)CCOC(c1ccccc1)(c1ccc(OC)cc1)c1ccc(OC)cc1 | null | null | null |
1,758,286 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | COC1C=CC=CC=1O[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[OH:8].[O-]S([O-])(=O)=O.[Mg+2]>[Ni].CCOCC>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7](=[O:8])[CH3:6])=[CH:10][CH:11]=1 | COc1ccc(C(O)COc2ccccc2OC)cc1 | null | null | [Ni] | O=S(=O)([O-])[O-] | [Mg+2] | 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 | 80 | null | To a vial was added wet Raney Ni 4200 (8 mg, 7×10−5 mol, 50 mol %), then 3 mL degassed hexane followed by 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol (38 mg, 1.4×10−4 mol). The vial was capped and heated to 80° C. for 24 hours. The reaction was cooled, opened and 10 mg of NH4COOH was added. 50 mL of Et2O was use... | COc1ccc(C(C)=O)cc1 | null | null | null |
999,367 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | CCOC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18]([N:20]1[CH2:24][C@@H:23]([CH2:25][N:26]([CH:42]([CH3:44])[CH3:43])[C:27](=[O:41])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:29]=2)[C@H:22]([CH2:45]O)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:47]1(=[O:57])[NH:51][C:50](... | COCCCOc1cc(C(=O)N(C[C@@H]2CN(C(=O)OC(C)(C)C)C[C@H]2CO)C(C)C)ccc1C | O=C1NC(=O)c2ccccc21 | 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 | O | null | null | null | null | null | null | null | null | null | null | null | DEAD is slowly added to a solution of (3S,4R)-3-hydroxymethyl-4-({isopropyl-[3-(3-methoxy-propoxy)-4-methyl-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (210 mg, 0.44 mmol), phthalimide (07 mg, 0.66 mmol) and PPh3 (173 mg, 0.66 mmol) in THF (5 mL) at RT. The resulting yellow solution is stirre... | COCCCOc1cc(C(=O)N(C[C@@H]2CN(C(=O)OC(C)(C)C)C[C@H]2CN2C(=O)c3ccccc3C2=O)C(C)C)ccc1C | null | null | null |
1,324,175 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[N:12]2)=[CH:6][CH:5]=1.O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]=[CH:14][C:13]([NH2:16])=[N:12]2)=[CH:6][CH:5]=1 | COC(=O)c1ccc(Cn2ccc([N+](=O)[O-])n2)cc1 | null | null | Cl[Sn]Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 1 | 4-(3-Nitro-pyrazol-1-ylmethyl)-benzoic acid methyl ester (530 mg, 2.03 mmol) was dissolved in ethyl acetate (10 ml). Tin(II) chloride dihydrate (2.29 gm, 10.15 mmol) was added, reaction mixture was heated at 70 deg C. for 1 h. The reaction mixture was cooled to ambient temperature, the pH adjusted to pH 8-9 by addition... | COC(=O)c1ccc(Cn2ccc(N)n2)cc1 | null | 102.2 | null |
1,234,045 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:35]=[CH:34][C:15]([O:16][C:17]2[C:18]([CH:23]3[CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]3)=[N:19][CH:20]=[CH:21][N:22]=2)=[CH:14][CH:13]=1)=[O:11].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:25]1[CH2:26][CH:23]([C:18]2[C:17]([O:16][C:15]3[CH:34]=[CH:35][C:12]([C:10... | CC(C)(C)OC(=O)N1CC(c2nccnc2Oc2ccc(C(=O)c3nc4ccccc4[nH]3)cc2)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 | 25 | 1 | To a solution of tert-butyl 3-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)azetidine-1-carboxylate (175 mg, 0.371 mmol) in CH2Cl2 (1 mL) is added 2,2,2-trifluoroacetic acid (1.0 mL). The reaction was stirred at rt 1 h. The solution was concentrated and CH2Cl2 (5 mL) and saturated NaHCO3 (0.5 mL) was adde... | O=C(c1ccc(Oc2nccnc2C2CNC2)cc1)c1nc2ccccc2[nH]1 | null | null | null |
368,526 | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | null | 1997-01-01T00:06:00 | true | [C:1]([C:9]1[C:10]([CH3:33])=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)=[CH:16][C:15]([O:29][CH3:30])=[C:14]([O:31][CH3:32])[CH:13]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:34]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([C:9]... | COc1ccc(-c2c(C(=O)c3ccccc3)c(C)nc3cc(OC)c(OC)cc23)cc1OC | O=C1CCC(=O)N1Br | null | CC(C)(C#N)N=NC(C)(C)C#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-benzoyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline (5.5 g), N-bromosuccinimide (2.42 g), 2,2'-azobis(isobutyronitrile)(0.815 g) and carbon tetrachloride (250 ml) was stirred under reflux for 1.5 hours. The reaction mixture was cooled, and then the insoluble material was filtered off. The fil... | COc1ccc(-c2c(C(=O)c3ccccc3)c(CBr)nc3cc(OC)c(OC)cc23)cc1OC | null | 42.1 | null |
1,423,050 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[CH3:19][C@H:20]1[O:25][C@@H:24]([CH3:26])[CH2:23][NH:22][CH2:21]1>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:21][C@@H:20]([CH3:19])[O:25][C@@H:24]([CH3:26])[CH2:23]2)[C:5]2[CH2:10][CH2:9][CH:8]([C:11... | Fc1ccc(C2CCc3c(Cl)nc(Cl)nc32)cc1 | C[C@@H]1CNC[C@H](C)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 2,4-dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (Preparation H) (200 mg, 0.706 mmol) in MeOH (7064 mL) was added cis-2,6-Dimethylmorpholine (105 mL, 0.848 mmol). The resulting mixture was stirred at RT overnight. An additional 2 equ. of cis-2,6-Dimethylmorpholine was then added a... | C[C@@H]1CN(c2nc(Cl)nc3c2CCC3c2ccc(F)cc2)C[C@H](C)O1 | null | 87.3 | null |
543,234 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | [CH2:1]([O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I:24][C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1.O>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[O:31][C:27]1[CH:28]=[CH:29][CH:30... | O=C(OCc1ccccc1)c1cccnc1Cl | Oc1cccc(I)c1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A solution 2-Chloro-nicotinic acid benzyl ester (1.7 grams, 6.86 mmole), cesium carbonate (4.5 grams, 13.7 mmole) and 3-iodophenol (1.7 grams, 7.54 mmole) in dimethylformamide (20 ml) was stirred for 2 hours at 70-80° C. The mixture was poured into 150 ml water and extracted with diethyl ether. The combined extracts we... | O=C(OCc1ccccc1)c1cccnc1Oc1cccc(I)c1 | null | null | null |
90,367 | ord_dataset-6ba93916f2ad4247804469d8c2600b26 | null | 1982-01-01T00:01:00 | true | [OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11])[CH2:3][NH2:4].[C:12](/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](=O)[CH3:26])=[CH:20][CH:19]=1)([O:14][CH3:15])=[O:13]>>[C:12](/[CH:16]=[CH:17]/[C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH:25]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]... | NCC(O)c1ccccc1F | COC(=O)/C=C/c1ccc(CC(C)=O)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 | This was prepared in an identical manner to the compound described in Example 1 using 2-hydroxy-2-(2-fluorophenyl) ethanamine (1.55 g) and 4-{(E)-2-carbomethoxyethenyl}phenylpropan-2-one (2.18 g). Elution with 1% methanolchloroform on Kieselgel 60 gave the title compound (1.2 g) m.p. 111°-116° C. (benzene-heptane) as a... | COC(=O)/C=C/c1ccc(CC(C)NCC(O)c2ccccc2F)cc1 | null | 33.6 | null |
1,620,101 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:21]3[N:26]=[CH:25][CH:24]=CN=3)[CH:16]=2)[C:11]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[C:35]1N=CC=C[N:36]=1>>[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:... | Brc1ncccn1 | Cc1cc2cc(-c3ncccn3)ccc2c(-c2ccc(Cl)cc2)c1[C@H](OC(C)(C)C)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 | (S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(pyrazin-2-yl)naphthalen-2-yl)acetic acid was prepared in a similar fashion to compound 59 with the substitution of 2-chloropyrazine for 2-bromopyrimidine in step 2. The title compound (0.026 g) was isolated as an amorphous pale yellow powder. LCMS-ESI+ (m/z): [M+H]+ c... | Cc1cc2cc(-c3cnccn3)ccc2c(-c2ccc(Cl)cc2)c1[C@H](OC(C)(C)C)C(=O)O | null | null | null |
879,748 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[CH2:27]O)=[O:21])([CH3:18])([CH3:17])[CH3:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:1... | O=[N+]([O-])c1ccc(C(F)(F)F)c(O)c1 | CC(C)(C)OC(=O)N1CCC[C@@H]1CO | 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 | 25 | 18 | To a solution of 5-nitro-2-trifluoromethylphenol (2.83 g, 13.7 mmol), (R)-(+)-(tert-butoxy-carbonyl)-2-pyrrolidinemethanol (2.75 g, 13.7 mmol), and PPh3 (3.58 g, 13.7 mmol) in 24 mL THF, cooled at −20° C. was added dropwise over 1.5 h a 12 mL THF solution containing DEAD (2.43 g, 13.9 mmol). The mixture turned a deep r... | CC(C)(C)OC(=O)N1CCC[C@@H]1COc1cc([N+](=O)[O-])ccc1C(F)(F)F | null | null | null |
1,224,022 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [CH3:1][N:2]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:20])[N:11]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CCN(CC)CC.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:1][N:2]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:20])[N:11]=1)[C:3]1[CH:4]=[CH:5][... | CS(=O)(=O)Cl | Cc1nc(N(C)c2ccc(N)cc2)c2ccccc2n1 | 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 | 25 | 16 | To a suspension of N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine 0.132 g (0.5 mmol) with Et3N 0.2 mL in CH2Cl2 10 mL was added methylsulfonyl chloride 0.115 g (1.0 mmol) at 23° C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with CH2Cl2 30 mL, washed with wat... | Cc1nc(N(C)c2ccc(NS(C)(=O)=O)cc2)c2ccccc2n1 | null | 15 | null |
1,314,803 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | CC1(C)OC(=O)[CH:5]([C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)[C:4](=[O:15])[O:3]1.Cl>O>[C:13]([C:9]1([CH2:5][C:4]([OH:15])=[O:3])[CH2:12][CH2:11][CH2:10]1)#[N:14] | CC1(C)OC(=O)C(C2(C#N)CCC2)C(=O)O1 | null | null | Cl | 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 | 100 | 2 | The reaction mixture of 1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)cyclobutanecarbonitrile (0.32 g, 1.4 mmol) in N,N-dimethylformate (4.0 mL) and water (0.40 mL) was stirred at 100° C. for 2 h. After cooled to r.t., the mixture was diluted with water, adjusted to pH=2 with aqueous HCl, and extracted with ethyl acetate (... | N#CC1(CC(=O)O)CCC1 | null | null | null |
266,053 | ord_dataset-a2ae447c4340438c8c3a827109aeb425 | null | 1993-01-01T00:04:00 | true | CC1(C)[O:7][CH2:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=2)([CH2:8][OH:9])[CH2:4][O:3]1.O>CO>[F:17][C:12]1[CH:11]=[C:10]([C:5]([CH2:8][OH:9])([CH2:4][OH:3])[CH2:6][OH:7])[CH:15]=[CH:14][C:13]=1[F:16] | CC1(C)OCC(CO)(c2ccc(F)c(F)c2)CO1 | null | null | null | null | 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 | 3 | 2,2-Dimethyl-5-(3,4-difluorophenyl)-5-hydroxymethyl-1,3-dioxane (1.0 g) and Dowex 50×8-200 ion exchange resin (H+ form) (100 mg) in methanol (100 ml) containing water (20 ml) was heated to reflux with stirring for 3 hours. The cooled solution was filtered and evaporated to leave 2-(3,4-difluorophenyl)-2-hydroxymethylpr... | OCC(CO)(CO)c1ccc(F)c(F)c1 | null | 53.3 | null |
1,256,214 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | Br[C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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)(... | COc1ccccc1B(O)O | Brc1cccc(-c2nnn[nH]2)c1 | 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 | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 8 | 5-(3-Bromo-phenyl)-1H-tetrazole 8b (20 g, 89 mmol) and 2-methoxybenzeneboronic acid (14.2 g, 93.3 mmol) were dissolved in 530 mL of 1,4-dioxane followed by addition of tetrakis(triphenylphosphine)palladium (1.84 g) and sodium carbonate (18.9 g, 178 mmol) under argon atmosphere. The reaction mixture was heated to reflux... | COc1ccccc1-c1cccc(-c2nnn[nH]2)c1 | null | 66.8 | null |
734,148 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[B:23](OC)([O:26]C)[O:24]C.Cl>CCCCCC.C1COCC1>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:23]([OH:26])[OH:24])=[CH:3][CH:4]=2)=[CH:9][C... | CCCCCCCCOc1ccc(-c2ccc(Br)cc2)cc1 | COB(OC)OC | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCC | null | null | null | null | null | null | null | null | null | -78 | 1 | A solution of n-butylithium (50.97 cm3, 0.1274 mol, 2.5M in hexane) was added dropwise to a cooled (−78° C.) stirred solution of 4-bromo-4′-octyloxybiphenyl (40.00 g, 0.1108 mol) in THF (400 cm3). After 1 h, trimethyl borate (23.05 g, 0.2216 mol) was added dropwise to the reaction mixture maintaining a temperature of −... | CCCCCCCCOc1ccc(-c2ccc(B(O)O)cc2)cc1 | null | 72.5 | null |
1,735,196 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[C:3]=1[C:17]#[N:18].C(=O)([O-])[O-:20].[K+].[K+].OO>CS(C)=O>[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[C:3]=1[C:17]([NH2:18])=[O:20] | N#Cc1c(Nc2ccc([N+](=O)[O-])cc2)n[nH]c1N | O=C([O-])[O-] | null | OO | [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 | 2 | Dissolved 5-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carbonitrile in DMSO (20 mL), added potassium carbonate (0.50 eq), then added hydrogen peroxide solution (1.8 mL of 30% solution in H2O) dropwise over ice bath over the course of 10 minutes. After the final addition, kept on ice bath for 2 hrs, then heated to roo... | NC(=O)c1c(Nc2ccc([N+](=O)[O-])cc2)n[nH]c1N | null | null | null |
773,628 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [C:1]([C:3]1[C:4]([S:10][C@@H:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12][NH:13]C(=O)OC(C)(C)C)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1)#[N:2].[ClH:27]>O1CCOCC1>[ClH:27].[NH2:13][CH2:12][C@@H:11]([S:10][C:4]1[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[C:6]([CH3:9])[N:5]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1 | Cc1ccc(C#N)c(S[C@H](CNC(=O)OC(C)(C)C)c2ccccc2)n1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | The product from step (c) (45 mg) was dissolved in 4M HCl in dioxane (5 ml). The resulting solution was stirred at room temperature for 15 minutes, then the solvent was evaporated off. The residue was recrystallised from diethyl ether/ethanol to give the title compound as a white solid (19 mg). | Cc1ccc(C#N)c(S[C@H](CN)c2ccccc2)n1 | null | null | null |
770,511 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [O:1]=[C:2]1[C:7]2[S:8][CH:9]=[C:10]([S:11](Cl)(=[O:13])=[O:12])[C:6]=2[CH2:5][CH2:4][CH2:3]1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]([OH:26])[CH2:23][NH:24][CH3:25])=[CH:18][CH:17]=1>>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:22]([OH:26])[CH2:23][N:24]([CH3:25])[S:11]([C:10]2[C:6]3[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[... | CNC[C@@H](O)c1ccc(F)cc1 | O=C1CCCc2c(S(=O)(=O)Cl)csc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | From 7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chloride (the compound of Preparation Example 7) (285 mg) and (1S)-1-(4-fluorophenyl)-2-(methylamino)ethanol (the compound of Preparation Example 38) (230 mg), the title compound (370 mg) was obtained as a light brown solid, in the same way as Preparation Exampl... | CN(C[C@@H](O)c1ccc(F)cc1)S(=O)(=O)c1csc2c1CCCC2=O | null | null | null |
1,223,288 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH3:17])[CH:8]=1)=O.Cl.[C:20]([C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH2:31])=[NH:30])[CH:25]=[CH:26][CH:27]=1)#[N:21]>>[CH2:16]([N:9]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:15]2[C:7]([C:5]2[CH:4]=[CH:3][N:31]=[C:29]([NH:28][C:2... | CCn1cc(C(=O)/C=C/N(C)C)c2cccnc21 | N#Cc1cccc(NC(=N)N)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 | Prepared by treatment of (E)-3-(dimethylamino)-1-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one and 1-(3-cyanophenyl)guanidine hydrochloride. 1H-NMR (DMSO-d6) δ: 1.48 (t, 3H, J=7.2 Hz, CH3), 4.39 (q, 2H, J=7.2 Hz, CH2), 7.27 (m, 1H, Ar—H), 7.36 (d, 1H, J=4.4 Hz, Pyrimidin-H), 7.42 (m, 1H, Ph-H or Ar—H), 7.51 (m... | CCn1cc(-c2ccnc(Nc3cccc(C#N)c3)n2)c2cccnc21 | null | null | null |
78,356 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [SH:1][CH2:2][CH2:3][NH:4][C:5]([NH:10][CH3:11])=[CH:6][N+:7]([O-:9])=[O:8].[CH3:12][N:13]([CH2:15][C:16]1[O:20][C:19]([CH2:21]O)=[CH:18][CH:17]=1)[CH3:14]>Cl.O.C(=O)([O-])[O-].[K+].[K+]>[CH3:12][N:13]([CH2:15][C:16]1[O:20][C:19]([CH2:21][S:1][CH2:2][CH2:3][NH:4][C:5]([NH:10][CH3:11])=[CH:6][N+:7]([O-:9])=[O:8])=[CH:18... | CNC(=C[N+](=O)[O-])NCCS | CN(C)Cc1ccc(CO)o1 | null | Cl | O=C([O-])[O-] | [K+] | 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 | 168 | N-(2-Mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (2 ml) was added dropwise to 5-(dimethylamino)methyl-2-furanmethanol (428 mg) at 0°. After standing at 0° for 7 days the reaction was diluted with water (3 ml), excess potassium carbonate was added and the solid extracted... | CNC(=C[N+](=O)[O-])NCCSCc1ccc(CN(C)C)o1 | null | null | null |
613,007 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[N:6][CH:7]=1.[C:18]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]([C:24](Cl)=[O:25])=[CH:20][CH:19]=1>ClCCl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH... | Nc1ccccc1C(=O)Nc1ccc(Cl)cn1 | O=C(Cl)c1ccc(-c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of N-(5-chloropyridin-2-yl)-2-aminobenzamide(0.247 g, 1 mmol) in dichloromethane (10 mL) and pyridine (0.5 mL) was added a solution of 4-biphenylcarbonyl chloride (0.217 g, 1 mmol) in dichloromethane (5 mL). After stirring overnight the solvent was removed in vacuo. The residue was partitioned between eth... | O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(-c2ccccc2)cc1 | null | 93.5 | null |
678,133 | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | null | 2005-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]=[CH:8]2.[C:15](Cl)(=[O:17])[CH3:16].[Cl-].[Cl-].[Cl-].[Al+3]>>[C:15]([C:6]1[CH2:7][CH2:8][C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH:5]=1)(=[O:17])[CH3:16] | CC(=O)Cl | COc1ccc(OC)c2c1C=CCC2 | null | [Al+3] | [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 | In spite of the fact that in literature the attempts of acylating the compound II were reported as fruitless or non interesting because of the low yields, the 5,8-dimethoxy-3,4-dihydronaphthalene II is treated with acetyl chloride in the presence of an excess of aluminium trichloride, preferably 5-9 moles of aluminium ... | COc1ccc(OC)c2c1C=C(C(C)=O)CC2 | null | null | null |
1,166,057 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [F:1][C:2]1[C:3]([CH3:18])=[N:4][C:5]2[N:6]([N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:11]=2)[C:7]=1O.O=P(Cl)(Cl)[Cl:21]>ClCCl>[Cl:21][C:7]1[N:6]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:11]=[C:5]2[N:4]=[C:3]([CH3:18])[C:2]=1[F:1] | Cc1nc2cc(-c3ccccc3)nn2c(O)c1F | O=P(Cl)(Cl)Cl | 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 | null | A solution of 6-fluoro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-ol x133 (25 mmol, 1 eq, 6.2 g) in POCl3 (150 ml) is heated at 125° C. overnight. After cooling to room temperature, the solution is diluted in dichloromethane and quenched on ice (temperature must be kept under 25° C.). After separation of the organic l... | Cc1nc2cc(-c3ccccc3)nn2c(Cl)c1F | null | 89 | null |
139,591 | ord_dataset-7d359d96b3a64882921ebdc6c850e22e | null | 1986-01-01T00:01:00 | true | S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:8]=1[OH:15]>>[Cl:4][C:9]1[C:10]([Cl:14])=[C:11]([Cl:13])[CH:12]=[C:7]([Cl:6])[C:8]=1[OH:15] | Oc1cc(Cl)c(Cl)cc1Cl | O=S(=O)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As the concentration of sulfuryl chloride increases, over-chlorination occurs, i.e., the 2,4,5-trichlorophenol becomes chlorinated to form more 2,3,4,6-tetrachlorophenol. The 2,3,4,6-tetrachlorophenol present becomes unacceptably high when the ratio of sulfuryl chloride to dichlorophenol significantly exceeds 1.3 to 1. | Oc1c(Cl)cc(Cl)c(Cl)c1Cl | null | null | null |
985,535 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[C:17]([CH:20]=1)[CH:18]=O.N1CCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:18]/[C:17]3[CH:20]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=... | COc1ccc(Oc2ccc(Cl)cc2C=O)cc1 | O=C1Cc2ccc(Cl)cc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNC1 | CO | null | null | null | null | null | null | null | null | null | 70 | null | To the mixture of 6-chlorooxindole (8.3 g, 49.7 mmol) and 5-chloro-2-(4-methoxy-phenoxy)-benzaldehyde (13 g, 49.7 mmol) in methanol (100 mL) was added pyrrolidine (4.1 mL, 49.5 mmol) dropwise. The mixture was then heated at 70° C. for 3 h. After cooled to room temperature, the mixture was filtered and the precipitate w... | COc1ccc(Oc2ccc(Cl)cc2/C=C2\C(=O)Nc3cc(Cl)ccc32)cc1 | null | 75.6 | null |
236,885 | ord_dataset-56e7a343b17a4d6da818127ceb19589d | null | 1991-01-01T00:11:00 | true | [OH:1][C@H:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[C:5]#[N:6].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:27]1([CH3... | Cc1ccc(S(=O)(=O)Cl)cc1 | CCCCCC[C@@H](O)CC(C#N)c1ccc(-c2ccc(OC)cc2)cc1 | null | CN(C)c1ccncc1 | 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 | 8 | To a solution of 186 mg (0.53 mmol) of (4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile in 10 ml of pyridine were added a solution of 303 mg (1.6 mmol) of p-toluenesulfonyl chloride in 20 ml of pyridine and 10 mg of DMAP. The resulting mixture was stirred at room temperature overnight. The pyridine was then re... | CCCCCC[C@H](CC(C#N)c1ccc(-c2ccc(OC)cc2)cc1)OS(=O)(=O)c1ccc(C)cc1 | null | 48.5 | null |
1,617,047 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([CH3:17])=[C:12]([CH:18]2[CH2:20][O:19]2)[C:11]=1[O:21][CH3:22])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(O)C.[CH3:27][CH:28]([NH2:30])[CH3:29].CCN(C(C)C)C(C)C>>[Cl:16][C:14]1[C:13]([CH3:17])=[C:12]([CH:18]([OH:19])[CH2:20][NH:30][CH:28]([CH3:29])[CH3... | COc1c(C(C)NC(=O)OC(C)(C)C)cc(Cl)c(C)c1C1CO1 | CC(C)N | 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 | CCO | null | null | null | null | null | null | null | null | null | 80 | null | tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-oxiran-2-ylphenyl)ethyl]carbamate (100 mg, 0.29 mmol, from Example 190, Step 1) was stirred in ethanol (2.0 mL, 34 mmol), 2-propanamine (120 μL, 1.5 mmol) and DIPEA (260 μL, 1.5 mmol) was added. The mixture was stirred at 80° C. over the weekend. Purification by preparative L... | COc1c(C(C)NC(=O)OC(C)(C)C)cc(Cl)c(C)c1C(O)CNC(C)C | null | 4.9 | null |
183,970 | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | null | 1989-01-01T00:02:00 | true | [NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[CH:4][CH:3]=1.[Cl:19][CH2:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1.ClC1C=CC=CC=1Cl>[Cl:19][CH2:20][S:21]([NH:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:9][C:8]=2[Cl:... | Nc1ccnn1-c1c(Cl)cc(C(F)(F)F)cc1Cl | O=S(=O)(Cl)CCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1Cl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 0 | 5 | 10 g (0.034 mole) of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole are dissolved in 35 ml of pyridine. 21.4 g (0.068 mole) of 47% chloromethanesulphonyl chloride, dissolved in 1,2-dichlorobenzene, are added dropwise at 0° C. to 5° C. The mixture is stirred for five hours, during which the temperature slowly... | O=S(=O)(CCl)Nc1ccnn1-c1c(Cl)cc(C(F)(F)F)cc1Cl | null | 62.6 | null |
537,915 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [CH3:1][O:2][C:3]([C:5]1([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH2:21]([O:20][C:1... | COc1ccc(S(=O)(=O)Cl)cc1 | CC#CCOc1ccc(S(=O)(=O)C2(C(=O)OC)CCNCC2)cc1 | null | CN(C)c1ccccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 15 | To a solution of 4-(4-but-2-ynyloxy-benzenesulfonyl)-piperidine-4-carboxylic acid methyl ester (500 mg, 1.29 mmol) in methylene chloride (10 ml) was added triethylamine (261 mg, 2.58 mmol), 4-methoxyphenylsulfonyl chloride (320 mg, 1.55 mmol) followed by a catalytic amount of dimethylaminopyridine. The resulting mixtur... | CC#CCOc1ccc(S(=O)(=O)C2(C(=O)OC)CCN(S(=O)(=O)c3ccc(OC)cc3)CC2)cc1 | null | 87.7 | null |
461,908 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([C:16]([O:18]CC)=[O:17])[C:11]([O:13]CC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)C.O>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([C:16]([OH:18])=[O:17])[C:11]([OH:13])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | CCOC(=O)C(CCCc1ccccc1)C(=O)OCC | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of diethyl 3-phenylpropylmalonate (5.5 g) and potassium hydroxide (2.8 g, 2.5 eq) in ethanol (20 ml) and water (30 ml) was refluxed for 5 hours. Work-up as described in Example 37b) gave the title compound (4.3 g, 98%); νmax (CH2Cl2) 2940 (br), 1727 and 1413cm-1 ; δH (CDCl3) 1.73 (2H, m, CH2), 2.00 (2H, m, CH... | O=C(O)C(CCCc1ccccc1)C(=O)O | null | 97.9 | null |
1,561,164 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Cl.[C:2]1(=[O:12])[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[CH:5]=[CH:4][NH:3]1>[Pt]=O.C(O)(=O)C>[C:2]1(=[O:12])[CH:11]2[CH:6]([CH2:7][NH:8][CH2:9][CH2:10]2)[CH2:5][CH2:4][NH:3]1 | O=c1[nH]ccc2c1CCNC2 | null | null | O=[Pt] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | 5,6,7,8-tetrahydro-2H-2,6-naphthyridin-1-one hydrochloride (250 mg, 1.339 mmol), platinum oxide (100 mg) and glacial acetic acid (10 mL) are stirred under hydrogen (5 bar) at r.t. for 24 h. | O=C1NCCC2CNCCC12 | null | null | null |
1,666,179 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([NH2:8])=[O:7])=[C:4]([N+:12]([O-])=O)[CH:3]=1>CO.[C].[Pd]>[NH2:12][C:4]1[CH:3]=[C:2]([CH3:1])[CH:10]=[C:9]([CH3:11])[C:5]=1[C:6]([NH2:8])=[O:7] | Cc1cc(C)c(C(N)=O)c([N+](=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 | 25 | 14 | To a solution of 4,6-dimethyl-2-nitroaniline (3 g, 18.07 mmol) in acetic acid (20 mL) and 6 N HCl (60 mL) at 0° C. was added a solution of sodium nitrite (2.18 g, 31.62 mmol) in water (5 mL). The reaction mixture was stirred at 0° C. for 30 min after completion of addition and copper (I) cyanide (3.24 g, 3 mmol) was ad... | Cc1cc(C)c(C(N)=O)c(N)c1 | null | 95.4 | null |
341,220 | ord_dataset-4c84bc8a34e1469aa1b156355c91cdcc | null | 1996-01-01T00:10:00 | true | [Si:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2] | CC(C)(C)[Si](C)(C)Oc1ccccc1C=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 | 25 | 1 | A solution of 28 (200 mg) in methanol (5.5 ml) containing NaBH4 (28 mg) is stirred for 1 hour at room temperature. 29 (140 mg, 68%) is obtained after hydrolysis and customary extraction. | CC(C)(C)[Si](C)(C)Oc1ccccc1CO | null | 69.4 | null |
658,517 | ord_dataset-be508e976bbb4586a0cc3368302a62f8 | null | 2005-01-01T00:01:00 | true | O[C:2]1([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:17][CH3:18])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[O:19]1[CH2:21][C@H:20]1[CH2:22][O:23][C:24]1[C:32]2[CH2:31][CH2:30][O:29][C:28]=2[CH:27]=[CH:26][CH:25]=1>CO>[O:29]1[CH2:30][CH2:31][C:32]2[C:24]([O:23][CH2:22][C@@H:20]([OH:19])[CH2:21][N:5]3[C... | c1cc2c(c(OC[C@@H]3CO3)c1)CCO2 | CCc1c(C2(O)CCNCC2)sc2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution 4-hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidine (0.069 g, 0.281 mmol) and (S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan (0.054 g, 0.281 mmol) in methanol (3 mL) was heated at reflux for 18 hours, and then cooled and evaporated. The residue was purified using silica gel chromatography (dichloromet... | CCc1c(C2CCN(C[C@H](O)COc3cccc4c3CCO4)CC2)sc2ccccc12 | null | 35 | null |
1,476,115 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:10]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:9]1.[NH2:30][C:31]1[C:32]([C:38](O)=[O:39])=[N:33][C:34]([Br:37])=[CH:35][CH:36]=1>>[NH2:30][C:31]... | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccncc2N)C[C@H]1O[Si](C)(C)C(C)(C)C | Nc1ccc(Br)nc1C(=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 | Following Method 11 of Example 305, trans-(+/−)-tert-butyl 1-(3-aminopyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-ylcarbamate and 3-amino-6-bromo-picolinic acid was reacted yielding trans-(+/−)-tert-butyl 1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-yl-carbamate, ... | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccncc2NC(=O)c2nc(Br)ccc2N)C[C@H]1O[Si](C)(C)C(C)(C)C | null | 20 | null |
1,099,321 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.[Cl:22][CH:23]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:24](Cl)=[O:25]>>[Cl:22][CH:23]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:24]([N:1]1[CH2:2][C... | O=C1C(=O)c2ccccc2C2=C1SCC1(CCNCC1)O2 | O=C(Cl)C(Cl)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Compound 50 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, chloro(phenyl)acetyl chloride and conditions outlined in procedure N. M.p.=125-126° C.; 300 MHz 1H NMR (DMSO-d6) δ 7.62-7.88 (m, 3H), 7.35-7.55 (m, 6H), 6.44 (d, 1H), 4.15 (m, 2H), 3.30 (m, 2H), 3.0-3.13 (2s, 2H), 2.0 (m, 2... | O=C1C(=O)c2ccccc2C2=C1SCC1(CCN(C(=O)C(Cl)c3ccccc3)CC1)O2 | null | null | null |
1,091,256 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][Mg]Cl)=[CH:5][CH:4]=1.[CH3:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23]>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][C:21]([C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]([NH:13][CH3:12])=[O:23])=[O:22])=[CH:5][CH:4]=... | CN1C(=O)c2ccccc2C1=O | COc1ccc(C[Mg]Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 0.08 | At 0° C., (4-methoxybenzyl)magnesium chloride (0.25 M in THF) (37 ml, 9.3 mmol) was added to 2-methylisoindoline-1,3-dione (1.00 g, 6.2 mmol) in THF (3.0 mL) (Reference: Synthetic Comm. 2004, 34(7), 1301-1308). The mixture was stirred at 0° C. for 5 minutes, then quenched with 10 mL of water. The reaction was warmed to... | CNC(=O)c1ccccc1C(=O)Cc1ccc(OC)cc1 | null | null | null |
426,034 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | F[C:2]1[CH:3]=[CH:4][C:5]([N+:31]([O-:33])=[O:32])=[C:6]([CH:30]=1)[C:7]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:8].CO.[CH3:36][NH:37][CH3:38]>C1COCC1>[CH3:36][N:37]([CH3:38])[C:2]1[CH:3]=[CH... | O=C(NCC1CCN(C(c2ccccc2)c2ccccc2)CC1)c1cc(F)ccc1[N+](=O)[O-] | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | Step 4): A mixture of 5-fluoro-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)-methyl]benzamide (13.4 g, 30 mmol) and 2.0M MeOH solution of dimethylamine (45 ml, 90 mmol) in THF (100 ml) was refluxed for 22 hours. The resulting solution was evaporated to give 5-dimethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methy... | CN(C)c1ccc([N+](=O)[O-])c(C(=O)NCC2CCN(C(c3ccccc3)c3ccccc3)CC2)c1 | null | null | null |
1,040,689 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | C([O:8][C:9]1[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][C:10]=1[CH2:11][N:12]([CH2:26][C:27]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=1)[C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:15][N:14]=1)C1C=CC=CC=1>... | CS(=O)(=O)CCOc1cnc(N(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)Cc2cc(C(F)(F)F)ccc2OCc2ccccc2)nc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 7 | (2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amine (1.07 g) is dissolved in ethanol (15 ml) and thereto is added 10% palladium-carbon (320 mg) and the mixture is stirred under hydrogen atmosphere at room temperature for 7 hours. The catalyst is re... | CS(=O)(=O)CCOc1cnc(N(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)Cc2cc(C(F)(F)F)ccc2O)nc1 | null | 42.8 | null |
1,681,708 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [C:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[OH:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:7][CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:10][CH2:9]2)=[CH:21][CH:20]=1 | CCOC(=O)c1ccc(N2CCC(NC(C)=O)CC2)cc1 | null | null | CC(C)C[AlH]CC(C)C | 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 | 0.33 | A solution of ethyl 4-(4-acetamidopiperidin-1-yl)benzoate (0.123 g, 0.42 mmol) in CH2Cl2 (10 mL) under nitrogen at −78° C. was treated with DIBAL-H (1.0M in hexanes, 0.950 mL, 0.95 mmol) dropwise, via a syringe. After 20 minutes, the mixture was warmed to room temperature, stirred for 1 hour, and quenched with 10% Roch... | CC(=O)NC1CCN(c2ccc(CO)cc2)CC1 | null | 24 | null |
154,511 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | [CH2:1]([O:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[BH4-].[Na+].CCCCCC>C(O)C>[CH2:1]([O:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9] | CCCCCCCCCOc1ccccc1C=O | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | CCO | null | null | null | null | null | null | null | null | null | 25 | 0.29 | 2-Hydroxybenzaldehyde (110 g), was alkylated by mixing this compound with 1-bromononane (180 g), anhydrous potassium carbonate and dimethylformamide (800 mL). This mixture was heated at 80° C. for 14 hours. Hexane and water were then added and the hexane extract was concentrated and the residue was distilled to yield t... | CCCCCCCCCOc1ccccc1CO | null | null | null |
278,854 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | [ClH:1].Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[CH2:4]2.[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[ClH:1].[N:3]12[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10]1)[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][CH:13]... | Nc1ccc(OC2CN3CCC2CC3)cc1 | CC(=O)OC(C)=O | 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 | null | null | 4-[(1-azabicyclo[2.2.2]oct-3-yl)oxy]benzenamine (Example 3) was acetylated with acetic anhydride in dry pyridine at -10° C. The crude product was converted into the hydrochloric salt to obtain N-[4-[(1-azabicyclo[2.2.2]-oct-3-yl)oxy]phenyl]acetamide hydrochloride. M.p. >250° C. | CC(=O)Nc1ccc(OC2CN3CCC2CC3)cc1 | null | null | null |
1,085,324 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].[BrH:20]>O.[Cu]Br>[Br:20][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([OH:7])=[O:6] | Br | Nc1cc(C(=O)O)ccc1OC(F)(F)F | null | [Cu]Br | O=N[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of 3-amino-4-trifluoromethoxybenzoic acid (2 g) in a mixture of water (16 ml) and 48% HBr (12 ml) at 0° C. was added a solution of sodium nitrite (0.64 g) in water (8 ml) drop-wise. After 15 min at 0° C. the reaction mixture was diluted with water (12 ml) and carefully poured onto a stirred soluti... | O=C(O)c1ccc(OC(F)(F)F)c(Br)c1 | null | null | null |
884,917 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1.[C:17]1([N:23]2[C:27]([C:28]3[O:29][CH:30]=[CH:31][CH:32]=3)=[CH:26][C:25]([CH:33]=O)=[N:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][CH2:10][N:11... | O=Cc1cc(-c2ccco2)n(-c2ccccc2)n1 | NCCN1CCN(c2ccccc2F)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 | Compound 67 was prepared using the same method as that of Example 1 except that 4-(2-fluorophenyl)piperazin-1-ylethylamine and 1-phenyl-5-(2-furyl)pyrazole-3-carbaldehyde were used. | Fc1ccccc1N1CCN(CCNCc2cc(-c3ccco3)n(-c3ccccc3)n2)CC1 | null | 86.3 | null |
660,264 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[NH2:26][C:27]1[CH:28]=[C:29]([CH:33]([OH:37])[CH2:34][NH:35][CH3:36])[CH:30]=[CH:31][CH:32]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:26][C:27]1[CH:... | Cc1c(CCl)sc2c(=O)c(C(=O)NCc3ccc(Cl)cc3)cn(C)c12 | CNCC(O)c1cccc(N)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 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 60 | 5 | A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (90 mg, 0.23 mmol), 1-(3-aminophenyl)-2-(methylamino)ethanol (Khim.-Farm. Zh 1983, 17, 1093)(69 mg, 0.42 mmol) and diisopropylethylamine (60 μL, 0.34 mmol) in dry DMF (4.6 mL) was heated to 60° C., becomin... | Cc1c(CN(C)CC(O)c2cccc(N)c2)sc2c(=O)c(C(=O)NCc3ccc(Cl)cc3)cn(C)c12 | null | 65.4 | null |
1,758,722 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH3:1][N:2]([CH3:15])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)(=[O:5])=[O:4]>CO.[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4])=[CH:7][CH:8]=1 | CN(C)S(=O)(=O)c1ccc([N+](=O)[O-])cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Under H2, N,N-dimethyl-4-nitrobenzenesulfonamide (879 mg, 3.8 mmol, 1.0 equiv.) was catalytically hydrogenated in the presence of Pd/C (40 mg) in MeOH (25 mL). When no more H2 was consumed, the reaction mixture was filtered. The filtrate was concentrated and crystallized to afford compound 4-amino-N,N-dimethyl benzenes... | CN(C)S(=O)(=O)c1ccc(N)cc1 | null | 94.9 | null |
960,959 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH2:1]([C@H:8]([NH:30][C:31](=[O:50])[C@H:32]([CH:47]([CH3:49])[CH3:48])[NH:33][C:34]([N:36]([CH2:38][C:39]1[N:40]=[C:41]([CH:44]([CH3:46])[CH3:45])[S:42][CH:43]=1)[CH3:37])=[O:35])[CH2:9][C@H:10]([OH:29])[C@@H:11]([NH:19][C:20]([O:22][CH2:23][C:24]1[S:28][CH:27]=[N:26][CH:25]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][... | CCCCSCCCC | CC(C)c1nc(CN(C)C(=O)N[C@H](C(=O)N[C@@H](Cc2ccccc2)C[C@H](O)[C@H](Cc2ccccc2)NC(=O)OCc2cncs2)C(C)C)cs1 | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC#N | null | null | null | null | null | null | null | null | null | 0 | 1 | To a solution of the compound of Example 1 (3.0 g, 4.2 mmol) and butyl sulfide (18 mL) in acetonitrile (24 mL) at 0° C. was added benzoyl peroxide (2.0 g) in three portions over 3 hours, and the reaction was stirred at 0° C. for 1 hour and then at room temperature for 1 hour. Additional benzoyl peroxide (4.0 g) was add... | CCCCSC(CCC)O[C@@H](C[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)N(C)Cc1csc(C(C)C)n1)C(C)C)[C@H](Cc1ccccc1)NC(=O)OCc1cncs1 | null | 68 | null |
1,545,119 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.[C:11]([NH2:15])(=O)[CH:12]=[CH2:13].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.P(Cl)(Cl)(Cl)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[C:11]([CH:12]=[CH:13][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1)#[N:15] | Cc1cc(Br)cc(C)c1N | C=CC(N)=O | null | [Pd+2] | CC(=O)[O-] | Cc1ccccc1P(c1ccccc1C)c1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | The third route disclosed in WO 03/016306 involved reaction of 4-bromo-2,6-dimethylphenylamine with acrylamide in presence of palladium acetate, tris(2-methylphenyl)phosphine and N,N-diethylethanamine. The resulting amide was dehydrated using phosphoryl chloride to give 4-(2-cyanoethenyl)-2,6-dimethylphenylamine in a m... | Cc1cc(C=CC#N)cc(C)c1N | null | 67 | null |
901,099 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)O)=[CH:4][CH:3]=1.[C:16]1([NH:22][C:23](=[O:25])[CH3:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(O)=O.OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:19]2[CH:20]=[CH:21][C:16]([NH:22... | OC(c1ccc(Cl)cc1)c1cccnc1 | CC(=O)Nc1ccccc1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of α-(4-chlorophenyl)-3-pyridinemethanol (0.364 mol) and N-phenyl acetamide (0.364 mol) in HOAc (360 ml) and H2SO4 36N (38.6 ml) was stirred and refluxed for 6 days. The solvent was evaporated, yielding 122.6 g (±)—N-[4-[(4-chloro-phenyl)(3-pyridinyl)methyl]phenyl]acetamide (compound 673). | CC(=O)Nc1ccc(C(c2ccc(Cl)cc2)c2cccnc2)cc1 | null | 100 | null |
1,715,400 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [BH4-].[Na+].[Cl:3][C:4]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].O>CO>[Cl:3][C:4]1[C:5]([CH2:6][OH:7])=[CH:8][CH:9]=[CH:10][C:11]=1[OH:12] | O=Cc1cccc(O)c1Cl | null | null | [BH4-] | [Na+] | 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 | 25 | 3 | To a solution of sodium borohydride (724 mg, 19.2 mmol) in anhydrous methanol (10 mL) was added a solution of 2-chloro-3-hydroxybenzaldehyde (1.0 g, 6.4 mmol) in anhydrous methanol (5 mL) at 0° C. The mixture was stirred for 3 hours at room temperature. Water was added and extracted 3 times with ethyl acetate. The comb... | OCc1cccc(O)c1Cl | null | 70 | null |
1,238,671 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [F:1][C:2]1[C:19]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])=[CH:18][CH:17]=[C:16]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1)=[O:5].[Cl:28]N1C(=O)CCC1=O>CN(C=O)C>[Cl:28][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:16]([F:27])=[CH:17]... | CCCS(=O)(=O)Nc1ccc(F)c(C(=O)Nc2cnc3[nH]ccc3c2)c1F | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 8 | 2,6-Difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.300 g, 0.7607 mmol) was dissolved in DMF (10 mL), and N-chlorosuccinimide (0.122 g, 0.913 mmol) was added and stirred overnight. The solution was partitioned between water and EtOAc. The organic portion was washed with water (3×), brine, d... | CCCS(=O)(=O)Nc1ccc(F)c(C(=O)Nc2cnc3[nH]cc(Cl)c3c2)c1F | null | null | null |
279,052 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | [H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[CH2:15][C:16](=[O:32])[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:21]([F:31])[CH:20]=1)[CH3:18]>CN(C)C=O>[F:31][C:21]1[CH:20]=[C:19]([CH:17]([CH3:18])[C:16](=[O:32])[CH2:15][CH:4]([C:5... | CC(C(=O)CCl)c1ccc(-c2ccccc2)c(F)c1 | CCOC(=O)CC(=O)OCC | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 2 | To a suspension of sodium hydride (1.88 g as 60% in oil, 47.0 mmoles) which was washed with hexane to remove mineral oil and dried, in dimethylformamide (DMF, 23 ml) was added dropwise a solution of diethyl malonate (7.52 g, 47.0 mmoles) in DMF (5 ml) at 0° C. under the stream of nitrogen gas. After elevating the tempe... | CCOC(=O)C(CC(=O)C(C)c1ccc(-c2ccccc2)c(F)c1)C(=O)OCC | null | 62 | null |
65,106 | ord_dataset-d986d6c6630b41ee8d401fd85be47701 | null | 1980-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([C:15]#[N:16])[CH2:10][C:11](OC)=[O:12])[CH:5]=[CH:6][CH:7]=1>[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][CH:9]1[CH2:15][NH:16][C:11](=[O:12])[CH2:10]1 | COC(=O)CC(C#N)Cc1cccc(Cl)c1 | null | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In the same manner as Example 1-(d), 5 g of methyl 4-(3-chlorophenyl)-3-cyanobutyrate was reduced with Raney's nickel as the catalyst to obtain 4-(3-chlorobenzyl)-2-pyrrolidinone. | O=C1CC(Cc2cccc(Cl)c2)CN1 | null | null | null |
1,177,231 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | 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]([CH3:41])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=2)=[CH:26][CH:25]=1>>[CH2:1]([O:8]... | O=C(O)C1CCCc2c(OCc3ccccc3)cccc21 | CC(C)c1ccc(NCc2ccc(N(C)C)cc2)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 (2.0 g) and [(4-dimethylaminophenyl)methyl](4-isopropylphenyl)amine (1.91 g) as starting materials, 5-benzyloxy-N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydrona... | CC(C)c1ccc(N(Cc2ccc(N(C)C)cc2)C(=O)C2CCCc3c(OCc4ccccc4)cccc32)cc1 | null | 20.1 | null |
441,256 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | [CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH:4]=[CH:5][CH2:6][C:7]1[C:8](=[O:19])[C:9]2[C:14]([C:15](=[O:18])[C:16]=1[OH:17])=[CH:13][CH:12]=[CH:11][CH:10]=2.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[C:8](=[O:19])[C:9]2[C:14]([C:15](=[O:18])[C:16]=1[OH:17])=[CH:13][CH:12]=... | CC(C)(C)CC=CCC1=C(O)C(=O)c2ccccc2C1=O | [H][H] | 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 | 2-(5,5-dimethylhex-2-enyl)-3-hydroxynaphthalene- 1,4-dione(3 91 mg) prepared in Example 45 was dissolved in ethyl acetate (15 ml) and hydrogenated as in Example 1(c) using hydrogen and 100 mg of Pd/C catalyst to provide 371 mg title compound. | CC(C)(C)CCCCC1=C(O)C(=O)c2ccccc2C1=O | null | 404.8 | null |
1,435,315 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | C([Li])CCC.[C:6]([O:10][C:11]([N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[F:25][C:26]1[N:37]=[CH:36][CH:35]=[CH:34][C:27]=1[C:28](N(OC)C)=[O:29]>O1CCCC1>[F:25][C:26]1[N:37]=[CH:36][CH:35]=[CH:34][C:27]=1[C:28]([C:22]1[S:21][C:20]([N:16]... | CC(C)(C)OC(=O)N1CCCN(c2nccs2)CC1 | CON(C)C(=O)c1cccnc1F | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 1 | A 2.5M n-butyl lithium in tetrahydrofuran solution (0.9 ml, 2.25 mmol) was added dropwise to a solution of tert-butyl-4-(thiazol-2-yl)-1,4-diazepane-1-carboxylate (570 mg, 2 mmol) in tetrahydrofuran (7 ml), cooled to −78° C. Thirty minutes later, a solution of 2-fluoro-N-methoxy-N-methylnicotinamide (370 mg, 2 mmol) in... | CC(C)(C)OC(=O)N1CCCN(c2ncc(C(=O)c3cccnc3F)s2)CC1 | null | 36.9 | null |
220,211 | ord_dataset-6cb04513a4a244c0b612b566096f4b3d | null | 1990-01-01T00:12:00 | true | [NH2:1][C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:5]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:4]=2[N:3]=1.[C:23]([C:30](OCC)=[O:31])#[C:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(O)C>[C:25]([C:24]1[N:3]2[C:4]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:5... | NC1=Nc2ccc([N+](=O)[O-])cc2C(c2ccccc2Cl)=NC1 | CCOC(=O)C#CC(=O)OCC | 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 | In the manner given in Example 27, 2-amino-7-nitro-5-(o-chlorophenyl)-3H-1,4-benzodiazepine was heated in ethanol with diethyl acetylenedicarboxylate to give 1-carboethoxy-9-nitro-7-(o-chlorophenyl)pyrimido[1,2-a][1,4]benzodiazepin-3(5H)-one. | CCOC(=O)c1cc(=O)nc2n1-c1ccc([N+](=O)[O-])cc1C(c1ccccc1Cl)=NC2 | null | null | null |
258,134 | ord_dataset-2369b9b9f44641b1930518c59ae89a95 | null | 1992-01-01T00:11:00 | true | Cl[C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]=[C:4]([NH:12][CH:13]=[O:14])[N:3]=1.[C:15]([O:18][CH2:19][CH:20]([CH2:31][O:32][NH2:33])[CH2:21][CH2:22][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])(=[O:17])[CH3:16].C(N(CC)C(C)C)(C)C>COCCOCCOC>[Cl:11][C:6]1[C:7]([NH:8][CH:9]=[O:10])=[C:2]([NH:33]... | O=CNc1nc(Cl)c(NC=O)c(Cl)n1 | CCOP(=O)(CCC(CON)COC(C)=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOCCOC | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 100 | 3 | 4,6-Dichloro-2,5-diformamidopyrimidine (0.390 g, 1.66 mmol), diethyl 3-(acetoxymethyl)-4-(aminooxy)-butylphosphonate (0.380 g, 1.275 mmol) and N,N-diisopropylethylamine (0.58 ml, 3.22 mmol) were dissolved in diglyme (15 ml) and the resulting mixture was stirred at 100° C. for 3 hours. The reaction mixture was then allo... | CCOP(=O)(CCC(CONc1nc(NC=O)nc(Cl)c1NC=O)COC(C)=O)OCC | null | 75.9 | null |
864,144 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][C:16]([CH3:23])([CH3:22])[C:15](=O)[C:14]=2[C:13]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:10])=[O:9]>C(O)(=O)C.S(=O)(=O)(O)O.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:2... | COC(=O)c1c(NS(=O)(=O)c2ccccc2F)ccc2c1C(=O)C(C)(C)CC2 | null | null | [Pd+2] | O=S(=O)(O)O | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of Example 362D (600 mg) and Pd(OH)2 on carbon (370 mg) in 50 mL of acetic acid and 0.6 mL of concentrated sulfuric acid was reacted under 60 psi pressure for 5 days. After insoluble was filtered off and the filtrate was concentrated in vacuo, the residue was purified by silica gel column chromatography eluti... | COC(=O)c1c(NS(=O)(=O)c2ccccc2F)ccc2c1CC(C)(C)CC2 | null | 5.2 | null |
157,240 | ord_dataset-58ec6779628e43e2b3f0972725f262e6 | null | 1987-01-01T00:05:00 | true | [Na].[CH2:2]([S:9][C:10]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:11]=1[C:12]([O:14]C)=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CN(C)C=O>[OH:14][C:12]1[C:11]2[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:10]=2[S:9][C:2]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1 | COC(=O)c1cc(C(F)(F)F)ccc1SCc1ccccc1 | null | null | [Na] | 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 | 0 | 1.5 | To a suspension of sodium hyride (50% dispersion in mineral oil) (0.49 g, 10.2 mmol) in N,N-dimethylformamide (30 ml) cooled to 0° C. in an ice-bath was added dropwise with stirring a solution of methyl 2-benzylthio-5-trifluoromethylbenzoate (2.5 g, 7.7 mmol) in N,N-dimethylformamide (10 ml). The reaction mixture was s... | Oc1c(-c2ccccc2)sc2ccc(C(F)(F)F)cc12 | null | null | null |
1,593,327 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][N:4]=1.I[CH2:16][CH3:17].CN(C=O)C.[H-].[Na+]>O>[CH2:16]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[C:3]([O:2][CH3:1])=[N:4]1)[CH3:17] | COc1n[nH]c2ccc([N+](=O)[O-])cc12 | CCI | 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 | 25 | 0.5 | 3-methoxy-5-nitro-1H-indazole (100 mg) and iodoethane (0.1 ml) were added to a DMF (1 ml) suspension containing sodium hydride (60% in oil) (23 mg), followed by stirring at room temperature for 0.5 hours. Water was added to the reaction solution. A solid precipitate was collected by filtration and purified by silica ge... | CCn1nc(OC)c2cc([N+](=O)[O-])ccc21 | null | null | null |
1,265,240 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][N:13]([CH2:22][C:23]2([N:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[CH2:29][CH2:28][CH:27]=[CH:26][O:25][CH2:24]2)[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[C:3]1=[O:37]>CCO.[Pd]>[CH3:1][N:2]1[C:11]2[C:6](=[... | CN1CCN(C2(CN(Cc3cc4ccccc4n(C)c3=O)C(=O)C3CCCCC3)CCC=COC2)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-{[3-(4-methylpiperazin-1-yl)-2,3,4,5-tetrahydrooxepin-3-yl]methyl}cyclohexanecarboxamide (59 mg, 0.116 mmole) was hydrogenated at atmospheric pressure (H2 balloon) with 10% Pd/C (13 mg, 0.012 mmole) in EtOH at RT. After 16 hr the mixture was filtered through a pad o... | CN1CCN(C2(CN(Cc3cc4ccccc4n(C)c3=O)C(=O)C3CCCCC3)CCCCOC2)CC1 | null | null | null |
557,736 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:15]1[CH:16]=[CH:17][C:18]([N+:30]([O-:32])=[O:31])=[C:19]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:20]=1.[H-].[Na+]>CN(C)C=O>[CH3:29][N:21]([C:19]1[CH:20]=[C:15]([O:13][C:8]2[CH:9]=[CH:10]... | CN(C(=O)OC(C)(C)C)c1cc(Cl)ccc1[N+](=O)[O-] | Oc1ccccc1-c1ccccc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | In a similar manner to that described in Reference Example 6, a reaction was carried out using 2-phenylphenol (3.5 g), t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (5.6 g), sodium hydride (55 wt. %, 1.08 g) and anhydrous N,N-dimethylformamide (35 ml) and the reaction mixture was purified to give the title compo... | CN(C(=O)OC(C)(C)C)c1cc(Oc2ccccc2-c2ccccc2)ccc1[N+](=O)[O-] | null | 101.1 | null |
1,078,688 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=4)=[C:14]([C:24]([NH:26][CH3:27])=[O:25])[C:13]=3[CH:28]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].N[C@@H:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:31][OH:32]>C1(Cl)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[F:23... | N[C@H](CO)c1ccccc1 | CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cccc(C#N)c3)cc12 | null | [Cl-] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | Zinc chloride (9 mg, 0.067 mmol) was added to a stirring solution of 5-(3-cyanophenyl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (50 mg, 0.135 mmol) and (S)-2-amino-2-phenylethanol (93 mg, 0.675 mmol) in PhCl (3 mL) rt. It was subjected to two interations of microwave irradiation at 200° C. for 1 hr. The mate... | CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cccc(C4=N[C@@H](c5ccccc5)CO4)c3)cc12 | null | 24.2 | null |
383,847 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:12]1COCC1>>[CH3:12][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:1]([NH2:9])=[O:8] | NC(=O)c1ccccc1 | C1CCOC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 60 | null | Treat the product of step 5 (10.54 g, 23.3 mmol) in THF (170 mL) with 60% NaH (1.87 g, 47 mmol) followed by CH31I (1.9 mL, 30.5 mmol). Heat the reaction mixture at 60° C. for 30 min and then partition between Et2O (250 mL) and H2O (500 mL). Extract the aqueous layer with Et2O (500 mL), wash the combined organic layers ... | Cc1ccccc1C(N)=O | null | 91 | null |
672,733 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[CH:11]1([CH:14]([OH:26])[CH2:15][CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH:3]=1)[O:26][CH:14]([CH:11]1[CH2:12][CH2:13]1)[CH2:15][CH2:16][N:17]([CH3:... | N#Cc1ccc(Cl)cc1F | CN(CCC(O)C1CC1)C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the method of Example 3 step (b) but using 4-chloro-2-fluorobenzonitrile and (3-cyclopropyl-3-hydroxypropyl)methylcarbamic acid, 1,1-dimethylethyl ester. | CN(CCC(Oc1cc(Cl)ccc1C#N)C1CC1)C(=O)OC(C)(C)C | null | null | null |
140,789 | ord_dataset-a2a0fbbcd49a46ffaa432d7ceae8a506 | null | 1986-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[N:27][C:28]#[N:29])SC)=[C:9]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].O.[NH2:36][NH2:37]>C(O)C>[NH2:29][C:28]1[N:27]=[C:24]([NH:23][CH2:22][CH2:21][O:20][CH2... | CCOC(=O)C1=C(COCCNC(=NC#N)SC)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | N-{2-[(4{-2-Chlorophenyl}-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl)methoxy]ethyl}-N'-cyano-S-methyl-isothiourea (0.4 g) and hydrazine hydrate (0.15 ml) were dissolved in ethanol (20 ml) and heated under reflux for 3 hours. The solvent was then evaporated and toluene (10 ml) was added to the res... | CCOC(=O)C1=C(COCCNc2nc(N)n[nH]2)NC(C)=C(C(=O)OC)C1c1ccccc1Cl | null | null | null |
528,480 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([O:18][CH3:19])[C:11]([F:17])=[CH:12][CH:13]=2)[N:8]([CH:20]2[CH2:22][CH2:21]2)[CH:7]=1)=[O:5])C.C(O)(=O)C.S(=O)(=O)(O)O>O>[CH:20]1([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[C:11]([F:17])[C:10]=3[O:18][CH3:19])[C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7]2)[CH2:21][CH... | CCOC(=O)c1cn(C2CC2)c2c(OC)c(F)ccc2c1=O | null | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | 0 | null | A quantity of 28.6 g of ethyl-1-cyclopropyl-1,4-dihydro-7-fluoro-8-methoxy-4-oxo-quinoline-3-carboxylate and 300 mL of a mixture of acetic acid, water, sulfuric acid (8/6/1) are refluxed for 2 hours. The reaction mixture is cooled at 0° C. and the desired product collected by filtration. | COc1c(F)ccc2c(=O)c(C(=O)O)cn(C3CC3)c12 | null | null | null |
1,144,001 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[O:15]=[C:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1>>[OH:15][C:16]1([C:7]2[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=... | CC(C)(C)OC(=O)N1CCCC(=O)C1 | COCCCn1cnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | -78 | null | 1-(3-methoxypropyl)-1H-benzo[d]imidazole (137A) (9.62 mmoles; 1.83 g) was added to an oven dried 250 mL round-bottomed flask equipped with an addition funnel and for stirring under nitrogen. Et2O (75 mL) was added and the solution was cooled to −78° C. with an acetone/CO2(s) bath. N-BuLi (2.5M in hexanes, 10.1 mmoles, ... | COCCCn1c(C2(O)CCCN(C(=O)OC(C)(C)C)C2)nc2ccccc21 | null | null | null |
1,460,310 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl.[CH3:2][O:3][CH2:4][CH2:5][O:6][CH2:7][C:8]([OH:10])=O.[CH2:11]([C@H:18]1[CH2:22][NH:21][C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([C@H:18]1[CH2:22][N:21](... | COCCOCC(=O)O | O=C(Nc1ccc(Oc2ccc(F)cc2)cc1)[C@@H]1C[C@@H](Cc2ccccc2)CN1 | 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 | Proceeding as in Example 1, but substituting 2-(2-methoxyethoxy)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 88, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(2-methoxyethoxy)acetyl)pyrrolidine-2-carboxamide (8.1 mg, 26.6%). Major isomer: 1H... | COCCOCC(=O)N1C[C@H](Cc2ccccc2)C[C@H]1C(=O)Nc1ccc(Oc2ccc(F)cc2)cc1 | null | 26.6 | null |
1,043,536 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([C@@H:19]1[O:24][CH2:23][C@@H:22]([OH:25])[CH2:21][CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:6]([C@@H:19]1[O:24][CH2:23][C@@H:22]([O:25][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:21][CH2:20]1)([C:13]1[CH:18]=... | O[C@H]1CC[C@H](C(c2ccccc2)c2ccccc2)OC1 | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | Methanesulfonyl chloride (0.33 g, 2.87 mmol) was reacted with trans-2-diphenylmethyl-tetrahydropyran-5-ol 11 (0.38 g, 1.43 mmol) in the presence of triethylamine (0.22 g, 2.15 mmol) in methylene chloride (10 ml) to give trains-2-diphenylmethyl-tetrahydropyran-5-yl methanesulfonate 13 (0.39 g, 77.8%) as an oil (Procedur... | CS(=O)(=O)O[C@H]1CC[C@H](C(c2ccccc2)c2ccccc2)OC1 | null | 78.7 | null |
1,063,546 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | C([C@@:9]1([OH:34])[C@@H:13]([CH:14](C(=O)C2C=CC=CC=2)[OH:15])[O:12][C@@H:11]([N:24]2[CH:31]=[CH:30][C:28](=[O:29])[NH:27][C:25]2=[O:26])[C@@:10]1([F:33])[CH3:32])(=O)C1C=CC=CC=1.N>CO>[F:33][C@:10]1([CH3:32])[C@H:9]([OH:34])[C@@H:13]([CH2:14][OH:15])[O:12][C@H:11]1[N:24]1[CH:31]=[CH:30][C:28](=[O:29])[NH:27][C:25]1=[O:... | C[C@]1(F)[C@H](n2ccc(=O)[nH]c2=O)O[C@H](C(O)C(=O)c2ccccc2)[C@]1(O)C(=O)c1ccccc1 | null | null | N | 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 | 0 | 0.5 | To a solution of 3′,5′-dibenzoyl-2′-Deoxy-2′-fluoro-2′-C-methyluridine (1.5 g, 1 eq) in MeOH (10 mL) was added a solution of saturated ammonia in MeOH (20 mL). The reaction mixture was stirred at 0° C. for 30 min, and then warmed to room temperature slowly. After the reaction mixture was stirred for another 18 hours, t... | C[C@@]1(F)[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O | null | 60 | null |
1,610,734 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([F:13])[C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[C:19]([F:26])=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][NH2:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([... | CC(C)(C)OC(=O)N1CC[C@H](F)[C@H]1C(=O)O | NCc1cccc(Cl)c1F | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 20 | To a solution of (2R,3S)-3-fluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (120 mg, 0.514 mmol) in CH2Cl2 (5 mL) were added successively 3-chloro-2-fluorobenzylamine (0.065 mL, 0.514 mmol), HBTU (293 mg, 0.772 mmol) and DIPEA (0.18 mL, 1.03 mmol), and stirring was continued at RT for 20 h. The reaction mixt... | CC(C)(C)OC(=O)N1CC[C@H](F)[C@H]1C(=O)NCc1cccc(Cl)c1F | null | null | null |
1,453,376 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Cl:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[N:16]=2)=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>ClCCl.CS(C)=O>[Cl:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18... | Fc1cccc(CNc2cccc(-c3cc(NC4CCNCC4)ncc3Cl)n2)c1 | CCS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 1 | A mixture of 5′-chloro-N6-(3-fluorobenzyl)-N2′-(piperidin-4-yl)-2,4′-bipyridine-2′,6-diamine (Example 6, 16 mg, 0.039 mmol), dichloromethane (0.5 ml), and TEA (0.022 ml, 0.155 mmol) was cooled to 0° C. This cooled mixture was then diluted with a solution of 0.03 ml of dichlormethane with ethanesulfonyl chloride (6.99 m... | CCS(=O)(=O)N1CCC(Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)CC1 | null | 50.4 | null |
576,982 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[Br:13]N1C(=O)CCC1=O>>[Br:13][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1 | O=C(O)c1ccc2cc[nH]c2c1 | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the procedure described in Example 34, Part A, indole-6-carboxylic acid (2.6 g, 16.1 mmol) and N-bromosuccinimide (2.9 g, 16.1 mmol) yielded 2.88 g (75%) of the title compound. | O=C(O)c1ccc2c(Br)c[nH]c2c1 | null | 74.5 | null |
1,480,791 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1.F[C:22]1[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[CH:24][N:23]=1>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][... | COc1ccc2c(c1)CCN(C1CCNCC1)C(=O)N2 | O=C(O)c1ccnc(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | null | null | 6.0 g (22 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 1.5 g (11 mmol) 2-fluoropyridine-4-carboxylic acid in 20 mL NMP were stirred overnight at 110° C. The reaction mixture was cooled and the precipitate formed was suction filtered. This was stirred with water, additionally combined ... | COc1ccc2c(c1)CCN(C1CCN(c3cc(C(=O)O)ccn3)CC1)C(=O)N2 | null | null | null |
1,370,472 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=4)=[CH:14][N:13]3[CH:25]=2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[O:22][C:21]([CH2:23][OH:24])=[CH:20][CH:19]=4)=[CH:14]... | O=Cc1ccc(-c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)o1 | 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 | 25 | 2 | 122 mg of sodium borohydride are added, in small portions, to 104 mg of 5-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-carbaldehyde dissolved in 20 ml of methanol. The mixture is subsequently stirred at ambient temperature for 2 hours, and the solvent is then evaporated off under reduced pressure. The residue ... | OCc1ccc(-c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)o1 | null | 37.3 | null |
11,424 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | [O:1]=[CH:2]C(Cl)(Cl)Cl.[NH2:7][CH2:8][C:9]1([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C(Cl)(Cl)Cl>[CH:2]([NH:7][CH2:8][C:9]1([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:1] | NCC1(N2CCCCC2)CCCCC1 | O=CC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 16 | Chloral (4.65 g.) was added dropwise to a cooled solution of 1-[1-(aminomethyl)cyclohexyl]piperidine (5.9 g) in dry chloroform (30 ml). The mixture was stirred at room temperature for 16 hrs. and then heated under reflux for 30 mins. The solution was evaporated to dryness and the oily residue re-evaporated with ether. ... | O=CNCC1(N2CCCCC2)CCCCC1 | null | 75.6 | null |
1,537,138 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | C(N(S(F)(F)[F:7])CC)C.C(=O)=O.CC(C)=O.O[C:18]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][C:18]([F:7])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32... | CCN(CC)S(F)(F)F | CC(C)(C)OC(=O)N1CCC(O)(c2ccccc2)CC1 | null | O=C(OO)c1cccc(Cl)c1 | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(C)=O | null | null | null | null | null | null | null | null | null | -78 | 1 | A solution of diethylaminosulfur trifluoride (4 mL, 32.7 mmol) in dichloromethane (10 mL) was added to a cold (−78° C.; dry ice/acetone bath) solution of tert-butyl 4-hydroxy-4-phenylpiperidine-1-carboxylate (8.05 g, 29.0 mmol) in dichloromethane (100 mL) under nitrogen. The reaction was stirred at −78° C. for ˜1 hour.... | CC(C)(C)OC(=O)N1CCC(F)(c2ccccc2)CC1 | null | 102.1 | null |
279,713 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | C[C@@:2]1(O[C@H:10]([CH2:12]Br)[C@@:8]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:9])[C@:6]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([OH:7])[C@:4]1([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[OH:5])[OH:3]>C(O)(C)C.O.[Zn]>[C:32]1([CH2:31][O:30][C@@:4]([C@:6](... | C[C@]1(O)O[C@H](CBr)[C@](O)(OCc2ccccc2)[C@@](O)(OCc2ccccc2)[C@@]1(O)OCc1ccccc1 | null | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | Mix methyl-2,3,4-tris(phenylmethoxy)-6-bromo-6-desoxy-α-D-mannopyranose (20.968 g, 39.75 mmol) and activated zinc dust (20.50 g, 314 mmol) in isopropanol (300 mL) and water (55 mL). Heat at reflux for 38 minutes, cool and filter. Rinse the zinc dust with a mixture of ethyl acetate/water, filter and dilute the filtrate ... | C=C[C@](O)(OCc1ccccc1)[C@@](O)(OCc1ccccc1)[C@](O)(C=O)OCc1ccccc1 | null | null | null |
673,512 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[C... | O=C(O)COc1ccc(Cl)cc1 | CC(C)(C)OC(=O)N1CCC(N)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared following the method of Example 94 using (4-chlorophenoxy)acetic acid (0.50 g), 1,1-carbonyldiimidazole (0.50 g) and tert-butyl 4-amino-1-piperidinecarboxylate (0.46 g) to give the subtitle compound (0.54 g). | CC(C)(C)OC(=O)N1CCC(NC(=O)COc2ccc(Cl)cc2)CC1 | null | 63.7 | null |
1,275,083 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[CH2:6][N:5]([CH:14]([CH3:16])[CH3:15])[C:4]=2[N:3]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:21]([OH:23])=[O:22].Cl>O.O1CCOCC1>[CH:14]([N:5]1[C:4]2[N:3]=[C:2]([NH:17][C:18]3[CH:19]=[C:20]([CH:24]=[C:25]([C:27]([F:28... | CC(C)N1CC(=O)N(C)c2cnc(Cl)nc21 | Nc1cc(C(=O)O)cc(C(F)(F)F)c1 | null | Cl | null | null | 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 | 25 | null | 2-Chloro-8-isopropyl-5-methyl-7,8-dihydro-5H-pteridin-6-one (3.5 g; 14.54 mmol) and 3-amino-5-(trifluoromethyl)-benzoic acid (2.98 g; 14.54 mmol) were diluted in 15 ml of water and 15 ml of 1,4-dioxane, 2 ml of HCl 37% were added. The reaction mixture was refluxed 24 h, then cooled to room temperature. The desired prod... | CC(C)N1CC(=O)N(C)c2cnc(Nc3cc(C(=O)O)cc(C(F)(F)F)c3)nc21 | null | 80 | null |
1,028,892 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C([O-])(O)=O.[Na+].O=C1CCC(=O)N1[O:28][C:29](=O)[CH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(#N)C>O>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][C@H:2]([NH:1][C:2... | N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O | O=C(CCCc1ccccc1)ON1C(=O)CCC1=O | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | 25 | 12 | (Method J15B) A suspension of L-tryptophan (2.040 g, 10 mmol) and NaHCO3 in water (15 ml) was treated with 4-phenyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (15/95) (2.610 g, 10 mmol) followed by the addition of acetonitrile (ca. 15 ml) to get a clear solution. The reaction mixture was stirred at ambient temperatur... | O=C(CCCc1ccccc1)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O | null | 90.2 | null |
1,234,455 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | C(O[C:4]1[CH2:5][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][CH2:8][N:9]=1)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:25]([NH:27][NH2:28])=O)=[CH:20][CH:19]=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[C:32]([O:31][C:30]([NH:29][CH:24]([C:21... | CCOC1=NCCN(C(=O)OC(C)(C)C)C1 | CC(C)(C)OC(=O)NC(C(=O)NN)c1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of tert-butyl 3-ethoxy-5,6-dihydropyrazine-1(2H)-carboxylate (0.762 g, 3.34 mmol) and tert-butyl 1-(4-chlorophenyl)-2-hydrazinyl-2-oxoethylcarbamate (1.00 g, 3.34 mmol) in toluene (6.67 mL, 3.34 mmol) was heated to reflux and stirred at this temperature for 1 hour. The reaction mixture was cooled to room tem... | CC(C)(C)OC(=O)NC(c1ccc(Cl)cc1)c1nnc2n1CCN(C(=O)OC(C)(C)C)C2 | null | 59.4 | null |
317,080 | ord_dataset-eb32c2b9cbdf4fc39ce6c9fe0fa11430 | null | 1995-01-01T00:10:00 | true | Cl[SiH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>C1COCC1>[CH2:8]([CH:5]1[CH2:6][CH2:7][SiH:2]([SiH:2]2[CH2:7][CH2:6][CH:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[CH2:4][CH2:3]2)[CH2:3][CH2:4]1)[CH2:9][CH3:10] | FC(F)(F)c1ccc(C2CC[SiH](Cl)CC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 4.4 g (20 mmol) of 4-n-propylsilacyclohexyl bromide was dropped into a mixture of 0.5 g of magnesium (21 mmol) and 50 ml of THF to obtain Grignard reagent. This solution was then dropped into a 50 ml THF solution of 5.6 g (20 mmol) of 4-(4-chloro-4-silacyclohexyl)-1-trifluoromethylbenzene to obtain 4-(4-(4-n-propylsila... | CCCC1CC[SiH]([SiH]2CCC(c3ccc(C(F)(F)F)cc3)CC2)CC1 | null | 85 | null |
209,625 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | [CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][CH:5]([C:9](O)=O)[C:6]([OH:8])=[O:7].CNC.C=O>O>[CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5](=[CH2:9])[C:6]([OH:8])=[O:7] | Cc1ccccc1CC(C(=O)O)C(=O)O | null | null | C=O | CNC | 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 | 25 | 0.17 | To the acid of Step 2 (12.0 g, 0.11 mol) in H2O (25 ml) at 0° C., add 40% dimethylamine (12.9 ml, 0.115 mol), then another 12.0 g acid. Stir 10 min., add H2O (50 ml), then 38% formaldehyde (25 ml, 0.31 mol). Allow to warm to room temperature over 18 hr., filter the solid, slurry in H2O (200 ml), and heat at 90° for 2.5... | C=C(Cc1ccccc1C)C(=O)O | null | null | null |
1,336,745 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([N:14]3[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]3)[CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([N:14]3[CH2:15][CH2:16][CH:17]([OH:20])[CH2:18][CH2:19]3)[CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1 | O=C1CCN(c2cccc(-c3ccnc(Cl)n3)c2)CC1 | 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 | 25 | null | To a 0° C. solution of 1-(3-(2-chloropyrimidin-4-yl)phenyl)piperidin-4-one (200 mg, 0.7 mmol) in methanol (5 mL) was added NaBH4 (53 mg, 1.4 mmol). The reaction mixture was warmed to room temperature and monitored by TLC analysis. When the starting material had been consumed, the reaction was quenched with water and di... | OC1CCN(c2cccc(-c3ccnc(Cl)n3)c2)CC1 | null | null | null |
172,619 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | [N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16])=[C:2]=[O:3].[CH3:18][O:19][Si](C)(C)C>>[CH3:18][O:19][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[C:2]=[O:3] | O=C=NCCCCCCCCCCCC(=O)Cl | CO[Si](C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.1 mole 12-isocyanatododecanoic acid chloride was reacted as in Example 1 with 0.11 mole methoxytrimethyl silane at 75° C. until the acid chloride band at 1800 cm-1 had disappeared. The desired product was obtained after distillation. | COC(=O)CCCCCCCCCCCN=C=O | null | null | null |
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