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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
761,875 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | C([O:3][C:4](=[O:33])[C@@H:5]([O:30][CH2:31]C)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>>[CH3:31][O:30][C@@H:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:1... | CCOC(=O)[C@H](Cc1ccc(OCCCOc2ccc(N3CCOCC3)cc2)cc1)OCC | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (2S)-2-ethoxy-3-{4-[3-(4-morpholin-4-yl-phenoxy)-propoxy]-phenyl}-propionic acid ethyl ester (Step A) by standard hydrolysis procedure C (NaOH). 1H-NMR (CDCl3, 200.15 MHz): δ 9.90 (s, 1H), 7.30 (d, 2H, J=9.1), 7.10 (d, 2H, J=8.4), 6.91 (d, 2H, J=9.1), 6.75 (d, 2H, J=8.8), 4.18–3.90 ... | CO[C@@H](Cc1ccc(OCCCOc2ccc(N3CCOCC3)cc2)cc1)C(=O)O | null | null | null |
784,373 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH3:1][O:2][C:3](=[O:41])[CH:4]=[CH:5][CH:6]([NH:26][C:27](=[O:40])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:9]=1>CO.[Pd]>[CH... | COC(=O)C=CC(Cc1cn(CC=Cc2ccccc2)c2ccccc12)NC(=O)CCCCCCc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 5-[1-(3-Phenyl-allyl)-1H-indol-3-yl]-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid methyl ester (118 mg, 0.215 mmol) in MeOH (60 mL) was hydrogenated at 15 psi for 15 minutes using 10% Pd/C. The solution was filtered and the solvent removed to afford the title compound (111 mg, 93%). ESMS 553 (M+H+), mp 79.4-81° C. 1H ... | COC(=O)CC[C@@H](Cc1cn(CCCc2ccccc2)c2ccccc12)NC(=O)CCCCCCc1ccccc1 | null | 93.4 | null |
770,635 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:24][CH2:23][C@H:22]3[C@@H:18]([CH2:19][N:20]([C:25]4[CH2:29][CH2:28][C:27](=[O:30])[CH:26]=4)[CH2:21]3)[C@@H:17]2[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C[Si]([N-][Si](C)(C)... | C[C@@H](O[C@H]1CC[C@@H]2CN(C3=CC(=O)CC3)C[C@H]2[C@@H]1c1ccc(F)cc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | C1CCOC1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | -78 | 2 | To a solution of 20 mg (0.07 mmol) of 3-[(3aR,4R,5S,7aS)-5-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-4-(4-fluorophenyl)octahydro-2H-isoindol-2-yl]cyclopent-2-en-1-one (Example 7) and 170 mg (0.39 mmol) MoOPH in ˜2 mL dry THF under nitrogen atmosphere at −78° C. was added ×0.076 mL (0.15 mmol) of 2.0 M solution of... | C[C@@H](O[C@H]1CC[C@@H]2CN(C3=CC(=O)C(O)C3)C[C@H]2[C@@H]1c1ccc(F)cc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | null |
124,401 | ord_dataset-6d96290c60d941d098c4ddc9d0cb01a0 | null | 1984-01-01T00:12:00 | true | [CH2:1]([CH:3]1[C:7]2=[N:8][C:9]3[C:10]([F:17])=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]([OH:16])=[C:6]2[C:5](=[N:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[O:4]1)C.Cl.[OH2:25]>>[F:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([CH:3]([OH:25])[CH3:1])[C:6]([C:5]([NH:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[O:4])... | O | CCC1OC(=Nc2nccs2)c2c1nc1c(F)cccc1c2O | 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 | 50 | null | A mixture of 5 g of the product of Step F and 50 ml of 6N hydrochloric acid was heated at 50° C. for 5 hours and after addition of 50 ml of water, the mixture was cooled to 0° to 5° C. for 30 minutes and was vacuum filtered. The product was washed with water and dried under reduced pressure at 80° C. The product was su... | CC(O)c1nc2c(F)cccc2c(O)c1C(=O)Nc1nccs1 | null | null | null |
836,317 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [F:1][C:2]([F:18])([F:17])[C:3]([NH:5][C@@H:6]([CH3:16])[C@H:7]([OH:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[O:4].[N+:19]([O-])([OH:21])=[O:20].C(OCC)(=O)C>C(O)(=O)C>[F:1][C:2]([F:17])([F:18])[C:3]([NH:5][C@@H:6]([CH3:16])[C@H:7]([OH:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:19]([O-:21])=[O:... | O=[N+]([O-])O | C[C@H](NC(=O)C(F)(F)F)[C@H](O)c1ccc(O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC(=O)O | null | null | null | null | null | null | null | null | null | 0 | null | To a solution of 2,2,2-trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]acetamide (26.9 g) in acetic acid (85 mL) was added dropwise 70% nitric acid (6.78 mL) at room temperature with stirring. The mixture was stirred for 15 minutes at that temperature. The resulting mixture was poured into ice-water (5... | C[C@H](NC(=O)C(F)(F)F)[C@H](O)c1ccc(O)c([N+](=O)[O-])c1 | null | null | null |
1,644,089 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl.Cl[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6]1 | ClCCN1CCOCC1 | Oc1ccc2[nH]ccc2c1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 72 | A solution of 5-hydroxy-1H-indole (0.13 g, 1.0 mmol) in acetonitrile (10 mL) was successively added with N-(2-chloroethyl)morpholine hydrochloride (0.19 g, 1.0 mmol), and potassium carbonate (0.28 g, 2.0 mmol), and the mixture was stirred at room temperature for 72 hours. The solvent was evaporated under reduced pressu... | c1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | null | 48.7 | null |
433,089 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | Br[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[C:12]([CH3:15])[N:13]([CH3:14])[C:7]2=[N:6][C:5]=1[CH3:16].[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)[CH2:19][CH2:18]1.CC(NC(C)C)C>C(O)C>[N:23]1([CH:20]2[CH2:21][CH2:22][N:17]([CH2:2][CH2:3][C:4]3[C:9](=[O:10... | Cc1nc2n(C)c(C)cn2c(=O)c1CCBr | c1ccc2c(c1)ccn2C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)NC(C)C | CCO | null | null | null | null | null | null | null | null | null | null | null | A mixture of 6-(2-bromoethyl)-1,2,7-trimethyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one (8.85 g), prepared as described in EP-0,378,255, 1-(4-piperidinyl)-1H-indole (2 g) and N-(1-methylethyl)-2-propanamine (1.2 g) in ethanol (100 ml) was stirred and refluxed for 6 hours. The solvent was evaporated and the residue was stirre... | Cc1nc2n(C)c(C)cn2c(=O)c1CCN1CCC(n2ccc3ccccc32)CC1 | null | 62 | null |
1,712,572 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl-].[Si:2]([O:9][CH2:10][C@@H:11]1[CH:16]=[CH:15][C:14](=[O:17])[CH2:13][N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[BH4-].[Na+]>CO>[Si:2]([O:9][CH2:10][C@@H:11]1[CH:16]=[CH:15][C@H:14]([OH:17])[CH2:13][N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[C... | CC(C)(C)OC(=O)N1CC(=O)C=C[C@H]1CO[Si](C)(C)C(C)(C)C | null | null | [BH4-] | [Cl-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a stirred solution of cerious chloride (4.36 g, 11.71 mmol) and (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 50, 4.00 g, 11.71 mmol) in 50 mL MeOH at 0° C., NaBH4 (0.443 g, 11.71 mmol) was added as a solid. The mixture was stirred at ambient temp for... | CC(C)(C)OC(=O)N1C[C@@H](O)C=C[C@H]1CO[Si](C)(C)C(C)(C)C | null | 64.6 | null |
72,970 | ord_dataset-10f2568b472a4cabb35c3f313a159005 | null | 1980-01-01T00:11:00 | true | [SH2:1].[CH3:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13]>COCCOCCOC>[CH2:13]([SH:1])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH3:2] | S | C=CCCCCCCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOCCOC | null | null | null | null | null | null | null | null | null | null | null | null | Under the conditions of Example 3, with an input of 38 liters per hour of hydrogen sulphide, 67.7 mmoles of dodecene-1 dissolved in diglyme at a concentration of 0.564 mole per liter were irradiated at 11° C. After 3 minutes of irradiation, 48.2 mmoles of n-dodecyl mercaptan were formed. | CCCCCCCCCCCCS | null | null | null |
118,272 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | [CH3:1][C:2]([C:17]#[N:18])([CH3:16])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([C:14]#[N:15])([CH3:13])[CH3:12])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:12][C:11]([CH3:13])([CH2:14][NH2:15])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][C:2]([CH3:1])([CH3:16])[CH2:17][NH2:18])[CH:5]=1 | CC(C)(C#N)Cc1cccc(CC(C)(C)C#N)c1 | null | null | CC(C)C[Al+]CC(C)C | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | In a 1-liter flask equipped with a paddle stirrer, a reflux condenser capped with a nitrogen bubbler, and an addition funnel, was placed 7.50 g of 1,3-bis(2-methyl-2-cyanopropyl)benzene and 250 ml of reagent grade toluene which had been passed through acid alumina under nitrogen directly into the reaction vessel. With ... | CC(C)(CN)Cc1cccc(CC(C)(C)CN)c1 | null | null | null |
54,415 | ord_dataset-053897d9b1744303b2fdfe3e796ca27b | null | 1979-01-01T00:04:00 | true | [CH3:1][O:2][CH2:3][C:4]1([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9][CH2:8][N:7](CC2C=CC=CC=2)[CH2:6][CH2:5]1.[H][H]>[Pd].C(O)(=O)C>[CH3:1][O:2][CH2:3][C:4]1([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1 | COCC1(Nc2ccccc2)CCN(Cc2ccccc2)CC1 | [H][H] | null | [Pd] | 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 10 parts of 4-(methoxymethyl)-N-phenyl-1-(phenylmethyl)-4-piperidinamine and 200 parts of acetic acid is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filt... | COCC1(Nc2ccccc2)CCNCC1 | null | null | null |
622,968 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C@@H:7]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])[C:8](=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][S:34][C:35]1[N:36]=[CH:37][N:38]2[CH:42]=[C:41]([Sn](CCCC)(CCCC)CCCC)... | C[C@@H](O)[C@H]1C(=O)N2[C@@H](C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)[C@H](C)[C@H]12 | CCCC[Sn](CCCC)(CCCC)c1cn2cnc(SCc3ccccn3)c2s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The procedure of Example 1a) was repeated, except that 807 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 1.255 g of 7-(pyridin-2-yl)methylthio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds. Thus, 149 mg of 4-nitrobenzyl (1S,5R,... | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(c3cn4cnc(SCc5ccccn5)c4s3)[C@H](C)[C@H]12 | null | 11.3 | null |
428,004 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [NH2:1]N.[C:3]1(=[O:24])[N:7](CCCCON=C(OCC)C)[C:6](=[O:19])[C:5]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:4]12>>[C:3]1(=[O:24])[C:4]2[C:5](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:6](=[O:19])[N:1]=[N:7]1 | CCOC(C)=NOCCCCN1C(=O)c2ccccc2C1=O | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Briefly, N-(4-bromobutyl)phthalimide was treated with the anion of ethyl N-hydroxyacetimidate in tetrahydrofuran to yield ethyl N-[(4-phthalimidobutyl)oxy]acetimidate. The product was then treated with hydrazine to release the desired amine, ethyl N-[(4-aminobutyl)oxy]acetamidate, from the phthalimide. The desired amin... | O=C1N=NC(=O)c2ccccc21 | null | null | null |
999,759 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | C([O:3][C:4]([C:6]1[S:14][C:13]2[CH2:12][CH2:11][N:10]([C:15](OCC)=O)[CH2:9][C:8]=2[CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:15][N:10]1[CH2:11][CH2:12][C:13]2[S:14][C:6]([CH2:4][OH:3])=[CH:7][C:8]=2[CH2:9]1 | CCOC(=O)c1cc2c(s1)CCN(C(=O)OCC)C2 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 23 | 18 | 6,7-Dihydro-4H-thieno[3,2-c]pyridine-2,5-dicarboxylic acid diethyl ester (46 gram, 163 mmol) was dissolved in 200 ml THF. The solution was injected LAH (1M, THF) 300 ml at 23° C. Then it was stirred at 23° C. for 18 hrs. The reaction was quenched with 10 ml water and dried directly over sodium sulfate. Filter and conce... | CN1CCc2sc(CO)cc2C1 | null | 98.2 | null |
672,721 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [CH3:1][CH:2]([CH2:4][CH:5]([N:17]([CH3:19])[CH3:18])[C:6]1([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH2:9][CH2:8][CH2:7]1)[CH3:3]>C(OCC)(=O)C>[CH3:3][CH:2]([CH2:4][C@H:5]([N:17]([CH3:18])[CH3:19])[C:6]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH2:9]1)[CH3:1] | CC(C)CC(N(C)C)C1(c2ccc(Cl)cc2)CCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | null | 12.3 g of racemic sibutramine was dissolved in 85 ml of ethyl acetate, L-DBTA dissolved in 85 ml of ethyl acetate was added thereto. The reaction mixture was heated under reflux, cooled to room temperature and then filtered to obtain crystals (ee: about 85%). And then, the crystals were suspended in 220 ml of ethyl ace... | CC(C)C[C@H](N(C)C)C1(c2ccc(Cl)cc2)CCC1 | null | null | null |
18,739 | ord_dataset-8ca24382d55b4303bc34393399f4110e | null | 1977-01-01T00:01:00 | true | C[O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21].Cl.O>CO>[OH:21][C@H:12]1[CH2:11][CH2:10][C@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C@@H:18]1[C:5](=[CH:4][C:3](=[O:2])[CH2:20][CH2:19]1)[CH2:6... | COC1=CCC2=C(CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]32)C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | 15 | Dissolve dl-3-methoxyestra-2,5(10)-dien-17β-ol (0.84 g) in methanol (18 ml) containing concentrated hydrochloric acid (1.2 ml) and water (0.8 ml) and allow the mixture to stand at room temperature for 15 hours. Add water and extract the mixture with ether. Wash, dry and evaporate the ethanol solution and dissolve the r... | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O | null | 46.5 | null |
1,198,832 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([C:38](=[N:40]O)[NH2:39])=[N:35][C:34]=1[CH3:42])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O.ClCCl>[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([C:38]2[N:40]=[C:8]([CH... | Cc1nc(C(N)=NO)sc1C(=O)NCc1ccccc1 | O=C(O)Cc1ccccc1 | null | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of phenylacetic acid (0.05 g, 0.37 mmol) in N,N-dimethylformamide (2 mL) was added 1,1′-carbonyldiimidazole (0.14 g, 0.83 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, and N-benzyl-2-(N′-hydroxy-carbamimidoyl)-4-methylthiazole-5-carboxamide (0.12 g, 0.41 mmol) was added. The r... | Cc1nc(-c2noc(Cc3ccccc3)n2)sc1C(=O)NCc1ccccc1 | null | 6.9 | null |
1,519,060 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Cl.[CH3:2][C:3]1([CH3:26])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([C:15]3[N:16]=[C:17]([CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[S:18][CH:19]=3)[CH:6]=[CH:5][C:4]1=2.C(OC([NH:34][C@H:35]([C:39](O)=[O:40])[C@@H:36]([CH3:38])[OH:37])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:34][C@@H:35]([C@H:36]([OH:37])[C... | CC1(C)CCC(C)(C)c2cc(-c3csc(C4CCNCC4)n3)ccc21 | C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | The preparation was carried out analogously starting from 200 mg (0.47 mmol) of 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrochloride and 113 mg (0.52 mmol) of N-(tert-butoxycarbonyl)-L-threonine. The protecting group was cleaved off as already described using HCl in dioxane.... | C[C@@H](O)[C@H](N)C(=O)N1CCC(c2nc(-c3ccc4c(c3)C(C)(C)CCC4(C)C)cs2)CC1 | null | null | null |
198,364 | ord_dataset-f6fafbb8ce5f4ef099be3a772075ec97 | null | 1989-01-01T00:10:00 | true | [H-].[Na+].[C:3]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11][SH:12])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl[C:16]1[CH:21]=[N:20][N:19]([CH2:22][CH3:23])[C:18](=[O:24])[C:17]=1[CH3:25].O>CN(C)C=O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([CH2:11][S:12][C:16]2[CH:21]=[N:20][N:19]([CH2:22][CH3:23])[C:18](=[O:24])[C:17]=2[CH3:25])=[CH... | CCn1ncc(Cl)c(C)c1=O | CC(C)(C)c1ccc(CS)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | null | To 3 ml of dry N,N-dimethylformamide was added 0.024 g of 55% sodium hydride. The resulting mixture was kept at 0° C. and was added dropwise with a solution of 1 g of p-t-butylbenzyl mercaptan dissolved in 5 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution ... | CCn1ncc(SCc2ccc(C(C)(C)C)cc2)c(C)c1=O | null | 56.2 | null |
831,261 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | Br.C(O)(=O)C.C(OC(=O)[NH:15][C:16]1[N:17]([CH2:34][C:35]2[CH:43]=[CH:42][C:38]3[O:39][CH2:40][O:41][C:37]=3[CH:36]=2)[C:18](=[O:33])[C:19]2[C:24]([C:25]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:23][C:22]([Br:32])=[CH:21][CH:20]=2)C1C=CC=CC=1>>[NH2:15][C:16]1[N:17]([CH2:34][C:35]2[CH:43]=[CH:42][C:38]3[O:39]... | O=C(Nc1c(-c2ccccc2)c2cc(Br)ccc2c(=O)n1Cc1ccc2c(c1)OCO2)OCc1ccccc1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 25% Hydrogen bromide-acetic acid solution (10.0 ml) was added to [2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl]carbamic acid benzyl ester (3.6 g), and the mixture was stirred at room temperature for 1 hr. The precipitate was collected by filtration, washed with diethyl ether and dr... | Nc1c(-c2ccccc2)c2cc(Br)ccc2c(=O)n1Cc1ccc2c(c1)OCO2 | null | 119 | null |
478,018 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH:6]([OH:17])[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)C=[CH:9][CH:8]=1.[N:21]1C2C(=CC=CC=2)C(C=O)=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH:6]([OH:17])[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:21]=[CH:9][CH:8]=1 | O=Cc1ccnc2ccccc12 | COc1cccc(C(O)c2cccc3ccccc23)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 compound 26 was prepared by following the synthesis procedure as described for compound 1, but substituting 1-naphtaldehyde for 4-quinolinecarboxaldehyde. | COc1cccc(C(O)c2ccnc3ccccc23)c1 | null | null | null |
922,313 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](I)[CH3:17]>CN(C=O)C.CCOCC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:9][CH2:16][CH3:17])[CH:4]=1 | Oc1cc(Br)ccc1Cl | CCI | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOCC | null | null | null | null | null | null | null | null | null | 55 | null | To a solution of 2-chloro-5-bromophenol (WO98/003464 which is incorporated herein by reference, 3.43 g, 16.5 mmol) and K2CO3 (4.57 g, 33.0 mmol) in DMF (20 mL) was added ethyl iodide (1.78 mL, 22.3 mmol) at rt. The mixture was heated at 55° C. for 3.0 h. After cooling to rt, the reaction was diluted with ether, washed ... | CCOc1cc(Br)ccc1Cl | null | 99 | null |
1,541,012 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12](O)=[O:13].S(C)C>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13] | O=C(O)Cc1ccc([N+](=O)[O-])cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CSC | null | null | null | null | null | null | null | null | null | 25 | 10 | To a stirred solution of 2-(2-fluoro-4-nitrophenyl)acetic acid (1 g, 5.02 mmol) in tetrahydrofuran (10 mL) was added BH3.S(CH3)2 (7.5 mL, 7.53 mmol) at 0° C. The reaction mixture was allowed to stir at room temperature for 10 h. Then reaction mixture was cooled to 0° C. and the excess of borane was quenched with methan... | O=[N+]([O-])c1ccc(CCO)c(F)c1 | null | 95.8 | null |
921,464 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[O-]CC.[Na+].[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22](=[O:24])[CH3:23])[CH:17]=1.O>C(O)C>[CH2:9]([O:8][C:1](=[O:7])[C:2](=[O:4])[CH2:23][C:22]([C:18]1[CH:17]=[C:16]([CH3:15])[CH:21]=[CH:20][N:19]=1)=[O:24])[CH3:10] | CCOC(=O)C(=O)OCC | CC(=O)c1cc(C)ccn1 | null | CC[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | 0.17 | Diethyl oxalate (4.42 mL) was added to sodium ethoxide (2.22 g) in ethanol (22 mL), and the mixture was stirred for 10 minutes. The above-obtained 1-(4-methyl-2-pyridyl)ethanone (2.20 g) in ethanol (22 mL) was added to the mixture, followed by stirring at room temperature for 20 minutes. Water was added to the reaction... | CCOC(=O)C(=O)CC(=O)c1cc(C)ccn1 | null | null | null |
1,571,342 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11]Br)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:14]([NH:21][C:22]([NH2:24])=[NH:23])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CN(C=O)C>[C:17]([O:16][C:14]([N:21]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N:1]=[N+:2]=[N-:3])=[CH:5][CH:6]=2)=[CH:11][N:23]=[C:22]1[NH2:24])=[O:15])([CH3... | CC(C)(C)OC(=O)NC(=N)N | [N-]=[N+]=Nc1ccc(C(=O)CBr)cc1 | 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 | 25 | 48 | To a solution of 1-(4-azidophenyl)-2-bromoethanone (1.50 g, 6.24 mmol) in anhydrous DMF (20 mL) was added Boc-guanidine (3.00 g, 18.7 mmol). The reaction was stirred at ambient temperature for 48 hours upon which the mixture was partitioned between EtOAc (150 mL) and water (75 mL). The organic layer was successively wa... | CC(C)(C)OC(=O)n1c(-c2ccc(N=[N+]=[N-])cc2)cnc1N | null | 98.2 | null |
973,477 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][CH2:36][NH2:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1... | CC(C)(C)OC(=O)n1c(-c2ccc(Cl)c3c2C(=O)NC3)cc2cc(C=O)ccc21 | NCCc1cccs1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | In a similar manner to Step 1 of Example 56, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (20.0 mg, 0.0487 mmol) was dissolved in dichloromethane (0.5 mL). The solution was treated with thiophene-2-ethylamine (0.023 mL, 0.20 mmol) and sodium triacetoxyborohydride (32 mg, 0.15 mmol) to obtain 4-c... | CC(C)(C)OC(=O)n1c(-c2ccc(Cl)c3c2C(=O)NC3)cc2cc(CNCCc3cccs3)ccc21 | null | null | null |
1,601,995 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.Cl[C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1COCC1>[CH2:25]([O:24][C:22](=[O:23])[C:21]([NH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1])=[O:27])[CH3:26] | CCOC(=O)C(=O)Cl | COc1ccc(CN)c(OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 2.5 | 0.5 | A clean and dry jacketed reactor was equipped with a condenser, a Claisen adapter, a temperature probe, and an addition funnel or head column. The reactor was flushed with nitrogen gas for at least 15 minutes. The reactor was then charged with 1,396 g (1 equiv., 8.3 mol) of 2,4-dimethoxybenzylamine, 1,693 g (2 equiv., ... | CCOC(=O)C(=O)NCc1ccc(OC)cc1OC | null | 92.8 | null |
711,729 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([C:15]1[CH:31]=[CH:30][C:18]([CH2:19][NH:20][C:21](=[O:29])[CH:22]([O:26][CH2:27][CH3:28])[C:23]([OH:25])=O)=[CH:17][CH:16]=1)#[N:14].[C:32](=[N:40]O)([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[C:13]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][NH:20][C:21](=[O:29])[CH:22... | NC(=NO)c1ccccc1 | CCOC(C(=O)O)C(=O)NCc1ccc(C#N)cc1 | null | O=C(n1ccnc1)n1ccnc1 | 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 | 140 | 18 | To a solution under N2 of 1,1′-carbonyldiimidazole (272 mg) in THF (10 ml) was added a solution of (RS)-N-(4-cyano-benzyl)-2-ethoxy-malonamic acid (400 mg) in THF (10 ml). The mixture was stirred for 30 min before addition of a solution of benzamidoxime (228 mg) in THF (20 ml). After stirring 18 h the solvent was evapo... | CCOC(C(=O)NCc1ccc(C#N)cc1)c1nc(-c2ccccc2)no1 | null | null | null |
100,403 | ord_dataset-e984b2d4813f44d59867e1771acc9b66 | null | 1982-01-01T00:11:00 | true | [O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12.[C-:24]#N.[K+]>CC(O)C>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH:19]([CH3:24])[CH3:20])=[O:17])=[C... | [C-]#N | CCOC(=O)c1ncn2c1[C@@H]1CCCN1C(=O)c1ccccc1-2 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | null | 934 mg (3 mmol) of ethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate are stirred at 60° C. for 48 hours with 198 mg (3 mmol) of potassium cyanide in 30 ml of dry 2-propanol. The mixture is evaporated in vacuo. The residue is treated with 30 ml of 2-propanol and 198... | CC(C)OC(=O)c1ncn2c1[C@@H]1CCCN1C(=O)c1ccccc1-2 | null | null | null |
1,083,700 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [C:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]2)=[CH:11][CH:10]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C(O)=O.[Pd].CO>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8] | CCCCCCC#Cc1ccc(C2CCC(=O)C2)cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O=CO | null | null | null | null | null | null | null | null | null | null | 48 | Several drops of formic acid and catalytic amount 5% Pd/C was added to a 25 mL flask charged with 10 mL methanol and 1.34 g (5 mmol) of 2. The reaction vessel was flushed with H2, 3 times, and then mounted with a H2 balloon. After two days of hydrogenolysis, the solute was filtered through a pad of silica, and concentr... | CCCCCCCCc1ccc(C2CCC(=O)C2)cc1 | null | null | null |
1,740,871 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Cl.[CH:2]1([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=2[C:14]2[C:15]3[NH:22][C:21]([CH3:23])=[C:20]([C:24]([NH:26][C@@H:27]4[CH2:32][CH2:31][NH:30][CH2:29][C@H:28]4[OH:33])=[O:25])[C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:4][CH2:3]1.[C:34](Cl)(=[O:37])[CH2:35][CH3:36]>>[CH:2]1([CH2:5][O:6][C:7]2[CH:12]=[CH:1... | Cc1[nH]c2c(-c3cc(F)ccc3OCC3CC3)ncnc2c1C(=O)N[C@@H]1CCNC[C@H]1O | CCC(=O)Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 4-[2-(cyclopropylmethoxy)-5-fluorophenyl]-N-[(3R*,4R*)-3-hydroxypiperidin-4-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide hydrochloride (example D.f16) and commercially propionyl chloride the title compound is obtained as colorless solid. | CCC(=O)N1CC[C@@H](NC(=O)c2c(C)[nH]c3c(-c4cc(F)ccc4OCC4CC4)ncnc23)[C@H](O)C1 | null | null | null |
652,362 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[O:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:28]>O1CCOCC1>[ClH:28].[NH2:20][CH2:19][CH2:18][O:17][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:13]#[N:... | CC(C)(C)OC(=O)NCCOc1cc(C#N)ccc1OCc1ccccc1 | 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 | null | 8 | 3.4 g (9.2 mmol) of 4-benzyloxy-3-[2-(t-butoxycarbonylamino)ethoxy]benzonitrile was dissolved in 40 ml of 4 N solution of hydrogen chloride in dioxane, and the obtained solution was stirred overnight. The solvent was evaporated to obtain hydrochloride of the crude title compound. | N#Cc1ccc(OCc2ccccc2)c(OCCN)c1 | null | null | null |
220,677 | ord_dataset-42629b4cf1094978a5e5f29f22639ee7 | null | 1991-01-01T00:01:00 | true | C[Li].[N:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[CH:4]=1.[C:11]1(C)C=CC=CC=1>CCOCC>[CH3:11][C:4]1[C:5]([CH3:10])=[CH:6][C:7]([CH3:9])=[CH:8][N:3]=1.[N:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[CH3:11] | Cc1ccccc1 | Cc1cncc(C)c1 | null | [Li]C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | 4 | To 500 ml of a 5% solution of methyl lithium in ether were added dropwise at room temperature under argon 1200 ml of ether, subsequently 35.6 g of 3,5-lutidine (3,5-dimethylpyridine) and finally 400 ml of toluene. The ether was distilled off completely, whereupon the solution was stirred at 100° for 4 hours. Ice was th... | Cc1cnc(C)c(C)c1 | null | null | null |
119,881 | ord_dataset-9625b7c45a574cd58946dd2c1803eb6f | null | 1984-01-01T00:07:00 | true | [C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[CH2:3].C[O-].[Na+].[C:15](O)(=[O:17])C>CO>[CH3:15][O:17][CH2:3][CH:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:1]([O:10][CH3:11])=[O:9] | C=C(CC(=O)OC)C(=O)OC | CC(=O)O | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 96 | 200 g of dimethyl itaconate are dissolved, together with 5.9 g of sodium methoxide, in 650 ml of methanol and the solution is left to stand for four days. The solution is then acidified with acetic acid and fractionally distilled. 240 g (83.4% of the theoretical yield) of dimethyl 2-methoxymethylsuccinate are obtained,... | COCC(CC(=O)OC)C(=O)OC | null | 80.3 | null |
209,767 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | [C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:14](O)[CH3:15])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].S(Cl)([Cl:19])=O>C(Cl)Cl>[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:14]([Cl:19])[CH3:15])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2] | CC(=O)NC1Cc2ccc(C(C)O)cc2C1 | O=S(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 | null | 1 | 25 g (0.11 mol) of 1-(2-acetamido-indan-5-yl)-1-ethanol are suspended in 280 ml of methylene chloride, and 15 g (0.12 mol) of thionyl chloride are added. A clear solution is formed. After 1 hour, this solution is neutralised by washing with a saturated solution of sodium bicarbonate. The desired reaction product is obt... | CC(=O)NC1Cc2ccc(C(C)Cl)cc2C1 | null | null | null |
934,944 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[N:17]=[N:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)(=O)C>O.CO>[CH3:19][O:18][C:15]1[N:16]=[N:17][C:12]([CH2:11][OH:10])=[CH:13][C:14]=1[O:20][CH3:21] | COc1cc(COC(C)=O)nnc1OC | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 65 | 2 | A solution of potassium carbonate (0.2 g) in water 2 mL) is added to a solution of 6-acetoxymethyl-3,4-dimethoxypyridazine (0.27 g) in methanol (6 mL) and the mixture stirred at 60-70° C. for 2 hours. After evaporating to dryness the residue is partitioned between ethyl acetate (10 mL) and brine (10 mL). The ethyl acet... | COc1cc(CO)nnc1OC | null | null | null |
1,021,799 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [NH2:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[OH:9][CH2:8][C:3]1[C:2]([NH:1][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=[CH:5][N:4]=1 | Nc1cccnc1CO | O=C(Cl)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of (3-amino-pyridin-2-yl)-methanol (0.310 g, 2.54 mmol) and Et3N (0.570 g, 5.33 mmol) in dry CH2Cl2 (20 mL) was added benzoyl chloride (0.700 g, 5.08 mmol) dropwise. After the mixture was stirred for 18 h CH2Cl2 was removed, and then MeOH (5 mL) and saturated aqueous K2CO3 (25 mL) were added. The mixture ... | O=C(Nc1cccnc1CO)c1ccccc1 | null | null | null |
1,010,539 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][OH:22].[H-].[Na+].Br[CH2:26][C:27]#[C:28][CH3:29]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=2)[C:5]([... | CC#CCBr | CCOc1ccc(Cc2cc(Br)c(CCCO)cc2Cl)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.67 | To a stirred solution of 3-(2-bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol (BL) (0.268 g, 0.70 mmol) in 5 mL of THF was added NaH (0.034 g, 0.84 mmol, 60%) and stirred for 40 min. 1-bromo-2-butyne (0.094 mL, 1.05 mmol) was added and the mixture was stirred overnight at room temperature. The reaction was quenched... | CC#CCOCCCc1cc(Cl)c(Cc2ccc(OCC)cc2)cc1Br | null | 65.6 | null |
1,391,348 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [F:1][C:2]1[CH:28]=[C:27]([NH:29][C:30]([C:32]2([C:35](=[O:44])[NH:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)[CH2:34][CH2:33]2)=[O:31])[C:26]([F:45])=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([CH:14]2[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]2)=[O:13])[CH:6]=1.C(O)(C(F)(F)F)=O.C([O-])(... | CC(C)(C)OC(=O)N1CC(C(=O)Nc2cc(Oc3cc(F)c(NC(=O)C4(C(=O)Nc5ccc(F)cc5)CC4)cc3F)ccn2)C1 | null | null | O=C([O-])O | [Na+] | 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 | 8 | To a solution of tert-butyl 3-(4-(2,5-difluoro-4-(1-(4-fluorophenylcarbamoyl)cyclopropanecarboxamido)phenoxy)pyridin-2-ylcarbamoyl)azetidine-1-carboxylate (220 mg, 0.35 mmol) in CH2Cl2 (4 mL) was added TFA (0.2 mL) at 0° C. and the reaction was stirred at room temperature overnight. Saturated NaHCO3 solution was added ... | O=C(Nc1cc(Oc2cc(F)c(NC(=O)C3(C(=O)Nc4ccc(F)cc4)CC3)cc2F)ccn1)C1CNC1 | null | 8.7 | null |
1,377,580 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [C:1]1([CH:9]=[CH:10][C:11]2[CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=2)[CH:8]=[C:6]([OH:7])[CH:5]=[C:3]([OH:4])[CH:2]=1.[C:18](Cl)(=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>N1C=CC=CC=1>[C:18]([O:4][C:3]1[CH:2]=[C:1]([CH:9]=[CH:1... | Oc1ccc(C=Cc2cc(O)cc(O)c2)cc1 | CCCCCCCCCCCCCCCC(=O)Cl | 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 | 12 | Resveratrol (100 mg; 0.44 mmol) was dissolved in 1 mL of pyridine. Palmitoyl chloride (425 μL; 1.40 mmol; 3.2 equiv) was added with immediate solid formation noted. This mixture was stirred at ambient temperature for 12 h at which point HPLC analysis indicated no resveratrol present. The mixture was partitioned into et... | CCCCCCCCCCCCCCCC(=O)Oc1ccc(C=Cc2cc(OC(=O)CCCCCCCCCCCCCCC)cc(OC(=O)CCCCCCCCCCCCCCC)c2)cc1 | null | 108.4 | null |
651,847 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][N:19]2[CH2:24][CH2:23][N:22](C(OCC3C=CC=CC=3)=O)[CH:21]([CH3:35])[CH2:20]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:44])[N:13]2[C:36]1[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][C:37]=1[Cl:43].Br.CC(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]... | CC1CN(Cc2cc(-c3ccccc3Cl)c3c(c2)N(c2c(Cl)cccc2Cl)C(=O)NC3)CCN1C(=O)OCc1ccccc1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(=O)O | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a solution of benzyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}-2-methylpiperazine-1-carboxylate (105 mg, 0.16 mmol) in methylene chloride (2 mL) at 0° C. was added 30% HBr/HOAc (0.32 mL, 1.62 mmol) slowly. The resulting reaction mixture was stirred at 0° C. for 30 ... | CC1CN(Cc2cc(-c3ccccc3Cl)c3c(c2)N(c2c(Cl)cccc2Cl)C(=O)NC3)CCN1 | null | null | null |
1,530,543 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [CH3:1][O:2][C:3](=[O:30])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH:28]=C)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[O:31]1CCCC1>O=[Os](=O)(=O)=O.O>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O... | C1CCOC1 | C=Cc1c(C(F)(F)F)ccc2c1CC[C@H]2Oc1ccc2c(c1)OC[C@H]2CC(=O)OC | null | O=[Os](=O)(=O)=O | 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 | 50 | 8 | NaIO4 (1.80 g) and OsO4 (4% in water, 50 μL) are added to a mixture of {(S)-6-[(R)-5-trifluoromethyl-4-vinyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (1.25 g), tetrahydrofuran (16 mL), and water (4 mL) at room temperature. The mixture is stirred at 50° C. overnight. After cooling to room tem... | COC(=O)C[C@@H]1COc2cc(O[C@@H]3CCc4c3ccc(C(F)(F)F)c4C=O)ccc21 | null | null | null |
920,222 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [BrH:1].C(O)(=O)C.C(OC([NH:13][CH:14]1[CH2:18][CH2:17][N:16]([S:19]([C:22]2[C:23]3[C:24]([O:32]C)=[CH:25][N:26]=[CH:27][C:28]=3[CH:29]=[CH:30][CH:31]=2)(=[O:21])=[O:20])[CH2:15]1)=O)(C)(C)C>>[NH2:13][CH:14]1[CH2:18][CH2:17][N:16]([S:19]([C:22]2[C:23]3[C:24]([OH:32])=[CH:25][N:26]=[CH:27][C:28]=3[CH:29]=[CH:30][CH:31]=2... | COc1cncc2cccc(S(=O)(=O)N3CCC(NC(=O)OC(C)(C)C)C3)c12 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 0.5 | 30% Hydrogen bromide/acetic acid (1.5 ml, Tokyo Kasei Kogyo) is gradually added with Intermediate 13 (45 mg) obtained in Example 15, Step A at 0° C., and the mixture is stirred at the same temperature for 30 minutes. The solvent is concentrated under reduced pressure, and the obtained solid is collected by filtration t... | NC1CCN(S(=O)(=O)c2cccc3cncc(O)c23)C1 | null | null | null |
739,008 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=2)[N:6]=1.[CH2:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)[CH2:18][CH3:19]>>[CH2:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C:2]2[S:3][CH:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([NH:... | CC(=O)Nc1ccc(-c2csc(N)n2)cc1 | CCCc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from N-[4-(2-amino-1,3-thiazol-4-yl)phenyl]acetamide and 4-n-propylbenzenesulfonyl chloride as described in the synthetic METHOD B to give a yellow solid (1.0 mg) with purity >80%. MS (pos) m/z 416.2. | CCCc1ccc(S(=O)(=O)Nc2nc(-c3ccc(NC(C)=O)cc3)cs2)cc1 | null | null | null |
1,598,318 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](I)=[N:9]2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:18]([O:20]CC)=[CH2:19])CCC.Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:18](=[O:20])[CH3:19])=[N:9]2)=[CH:... | C=C(OCC)[Sn](CCCC)(CCCC)CCCC | Brc1ccc2ccc(I)nc2c1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | Cl | 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 | 100 | 1 | To a stirred slurry of 7-bromo-2-chloro-quinoline (obtained from AstaTech, Inc.), (8.10 g, 33.4 mmol) and sodium iodide (50.0 g, 334 mmol) in acetonitrile (27 mL) was slowly added acetyl chloride (3.56 mL, 50.0 mmol). The flask was stoppered and sealed and heated at 80° C. for 3 h before being allowed to cool. The mixt... | CC(=O)c1ccc2ccc(Br)cc2n1 | null | 66 | null |
143,910 | ord_dataset-1895fe091c3f47afa1ee96a41a250de4 | null | 1986-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5].S(=O)(=O)(O)[OH:13]>>[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]([NH2:5])=[O:13] | Cc1cc(Cl)c(C#N)c(Cl)c1 | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | null | To stirred, cooled concentrated sulfuric acid (40 ml) was added in portions 2,6-dichloro-4-methylbenzonitrile (13.2 g, 71.0 mmol). The mixture was heated on a steam bath for 3 hours with occasional shaking, cooled, poured into ice-water, and extracted twice with dichloromethane. The combined extracts were washed with b... | Cc1cc(Cl)c(C(N)=O)c(Cl)c1 | null | 59 | null |
529,058 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH:11]=[C:12]([CH3:18])[C:13](OCC)=[O:14]>C(O)C>[CH3:9][N:8]([CH3:10])[C:6]1[CH:7]=[C:2]2[C:3]([CH:11]=[C:12]([CH3:18])[C:13](=[O:14])[NH:1]2)=[CH:4][CH:5]=1 | CCOC(=O)C(C)=Cc1ccc(N(C)C)cc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | In a 30-ml Erlenmeyer flask made of quartz, 200 mg of (E) ethyl 3-(2-amino-4-dimethylaminophenyl)-2-methyl-2-propenate were dissolved in ethanol; and, while being stirred, the mixture was irradiated with ultraviolet rays at 365 nm for 48 hours. The reaction liquid was concentrated under a reduced pressure, and the resu... | Cc1cc2ccc(N(C)C)cc2[nH]c1=O | null | 98 | null |
1,097,204 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [CH2:1]([O:3][C:4](=[O:29])[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([CH2:16][N:17]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20](=[O:27])OC2=O)[CH:13]=[CH:12][N:11]=1)=[O:8])[CH3:2].Cl.[C:31]([C:33]1[CH:41]=[CH:40][C:36]([CH2:37][O:38][NH2:39])=[CH:35][CH:34]=1)#[N:32]>>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][NH... | CCOC(=O)CNC(=O)Nc1cc(Cn2c(=O)oc(=O)c3ccccc32)ccn1 | N#Cc1ccc(CON)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of 1-(2-amino-pyridin-4-ylmethyl)-1H-benzo[d][1,3]oxazine-2,4-dione (600 mg, see preparation 7b) in pyridine (7 ml) was added isocyanato-acetic acid ethyl ester (0.4 ml). The reaction mixture was stirred at room temperature for 3 hours, and the solvent was evaporated under reduced pressure. The re... | CCOC(=O)CNC(=O)Nc1cc(CNc2ccccc2C(=O)NOCc2ccc(C#N)cc2)ccn1 | null | null | null |
1,465,198 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].[CH2:24]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([N:35]2[CH2:38][CH2:37][CH:36]2[C:39]([O-])=[O:40])[CH2:31][CH2:30]1)=[O:28])[CH3:25].[L... | CCOC(=O)N1CCC(N2CCC2C(=O)[O-])CC1 | Cc1ccc(S(=O)(=O)[C@H]2CN[C@H](C(=O)NC3(C#N)CC3)C2)cc1 | null | [Li+] | null | null | null | null | null | 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 reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-tosylpyrrolidine-2-carboxamide 7G and lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylate 20J carried out according to the general procedure L yielded ethyl 4-(2-((2S,4R)-2-(1-cyanocyclopropylcarbamoyl)-4-tosylpyrrolidine-1-carbonyl)azetidin-1-yl)piperidi... | CCOC(=O)N1CCC(N2CCC2C(=O)N2C[C@H](S(=O)(=O)c3ccc(C)cc3)C[C@H]2C(=O)NC2(C#N)CC2)CC1 | null | null | null |
84,147 | ord_dataset-50c29bf1847c44f4b40bfab5f46fe5fe | null | 1981-01-01T00:08:00 | true | [CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=1)[CH3:2].[CH:14]([S:16]([F:19])(=[O:18])=[O:17])=[CH2:15]>C(O)(C)C>[F:19][S:16]([CH2:14][CH2:15][N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=1)(=[O:18])=[O:17] | C=CS(=O)(=O)F | CCNc1cccc(NC(C)=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | 2.5 | N-ethyl-m-acetamidoaniline (178.0 g, 1.0 m is dissolved in isopropyl alcohol (450 ml) and vinylsulfonylfluoride (110 g, 1.0 m) is added dropwise allowing temperature to rise to 40° C. The reaction is stirred for 2.5 hrs., the product collected by filtration, washed with cold ethanol and air dried. | CCN(CCS(=O)(=O)F)c1cccc(NC(C)=O)c1 | null | null | null |
1,557,525 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]([C:5]1[CH:9]=[C:8]([C:10]([NH:12][NH2:13])=[O:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:14]([C:16]1[O:20][C:19]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=2)=[CH:18][CH:17]=1)=O.C(O)C>>[C:1]([C:5]1[CH:9]=[C:8]([C:10](/[N:12]=[N:13]/[CH2:14][C:16]2[O:20][C:19]([C:... | N#Cc1ccc(-c2ccc(C=O)o2)cc1C(F)(F)F | CC(C)(C)c1cc(C(=O)NN)[nH]n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 36 | To the solution of 3-tert-butyl-1H-pyrazole-5-carbohydrazide (0.076 g, 0.41 mmol) in 10 ml of ethanol 4-(5-formylfuran-2-yl)-2-(trifluoromethyl)benzonitrile (0.10 g, 0.37 mmol) was added and the mixture was stirred at RT for 36 h. The solvent was evaporated and the residue purified with Combiflash using DCM/-methanol a... | CC(C)(C)c1cc(C(=O)/N=N/Cc2ccc(-c3ccc(C#N)c(C(F)(F)F)c3)o2)[nH]n1 | null | null | null |
744,280 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7](Cl)[S:6]1(=[O:13])=[O:12])([CH3:4])([CH3:3])[CH3:2].[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>>[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][OH:14])=[CH:17][CH:18]=2)[S:6]1(=[O:13])=[O:12])([CH3:4])([CH3:3])[CH3:2] | CC(C)(C)N1C(=O)C=C(Cl)S1(=O)=O | OCc1ccc(B(O)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 compound was prepared according to the procedure of Example 1.1, Step 4, using 9-A and 4-(hydroxymethyl)phenylboronic acid as the starting materials. 1H NMR (500 MHz, CDCl3): δ 7.77 (d, J=8.3 Hz, 2H), 7.52 (d, J=8.3 Hz, 2H), 6.64 (s, 1H), 4.79 (d, J=5.9 Hz, 2H), 1.86–1.84 (m, 1H), 1.73 (s, 9H); LCMS found for C14H... | CC(C)(C)N1C(=O)C=C(c2ccc(CO)cc2)S1(=O)=O | null | null | null |
1,327,405 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]4[N:18]5[N:19]=[C:20]([C:23](=O)[CH3:24])[CH:21]=[CH:22][C:17]5=[N:16][N:15]=4)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[CH2:27]([O:29][NH2:30])[CH3:28]>C(Cl)Cl>[CH2:27]([O:29]/[N:30]=[C:23](/[C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([C:11]3([C:7]4[CH:6]=... | CCON | CC(=O)c1ccc2nnc(C3(c4ccc5ncccc5c4)CC3)n2n1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-(3-(1-(quinolin-6-yl)cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (30 mg, 0.09 mmol) and O-ethyl-hydroxylamine hydrochloride (18 mg, 0.18 mmol) in 2 mL of DCM was stirred at 40° C. overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatograph... | CCO/N=C(\C)c1ccc2nnc(C3(c4ccc5ncccc5c4)CC3)n2n1 | null | null | null |
1,180,076 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[C:14]([CH3:22])=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17]>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[C:14]([CH3:22])=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])(=[O:10])=[O:9])=[CH:4][CH... | O=S(=O)(Cl)c1ccc(Br)cc1 | Cc1c(N)cccc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared using a method analogous to Method A, using 4-bromobenzene sulfonyl chloride, 3-amino-2-methylbenzoic acid, and a large excess of pyridine. The title compound was precipitated on partition of the reaction mixture between dilute HCl and DCM. The precipitate was collected by filtration, di... | Cc1c(NS(=O)(=O)c2ccc(Br)cc2)cccc1C(=O)O | null | null | null |
79,745 | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | null | 1981-01-01T00:04:00 | true | [H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[N:13]=[C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]2[C:20]([C:21]=1[C:22]#N)=[CH:19][CH:18]=[CH:17][CH:16]=2.C(O)(=[O:32])C.O>C1(C)C=CC=CC=1>[Cl:11][C:12]1[N:13]=[C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]2[C:20]([C:21]=1[CH:22]=[O:32])=[CH:19][CH:... | CC(=O)O | N#Cc1c(Cl)nc(-c2ccccc2)c2ccccc12 | null | CC(C)C[Al+]CC(C)C | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | 0 | 0.17 | In an atmosphere of argon and at -5° C. 10.7 ml of a 20% diisobutylaluminum hydride solution in toluene are slowly added dropwise to 2.64 g of 3-chloro-4-cyano-1-phenyl-isoquinoline in 150 ml of absolute toluene. The mixture is stirred for 10 minutes at 0° C. and then hydrolized with a small amount of glacial acetic ac... | O=Cc1c(Cl)nc(-c2ccccc2)c2ccccc12 | null | null | null |
678,982 | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | null | 2005-01-01T00:07:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]3)[N:9]=[C:10]([I:11])[C:3]=12.[ClH:24]>CC(C)=O>[ClH:24].[I:11][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[N:7][C:2]=2[NH2:1])[N:8]([CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[N:9]=1 | CC(C)(C)OC(=O)N1CCC(n2nc(I)c3c(N)ncnc32)C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 40 | 15 | A suspension of the crude tert-butyl 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinecarboxylate in acetone (100 mL) was treated with 6 N hydrochloric acid (50 mL). The reaction mixture was stirred at 40° C. for 15 hours. The initial precipitate was filtered and confirmed by LCMS to be impurities. The ... | Nc1ncnc2c1c(I)nn2C1CCNC1 | null | 31 | null |
1,618,514 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[C:3](Cl)=[O:4].N1C=CC=CC=1.[CH:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH2:18]>ClCCl>[CH2:20]([O:19][CH:17]=[CH:18][C:3](=[O:4])[C:2]([Cl:1])([F:10])[C:6]([F:9])([F:8])[F:7])[CH2:21][CH2:22][CH3:23] | O=C(Cl)C(F)(Cl)C(F)(F)F | C=COCCCC | 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 | 0 | 15 | With stirring and at 0° C., 9.59 g (48.2 mmol) of 2-chlorotetrafluoropropionyl chloride were added dropwise to a mixture of 4.19 g (50.0 mmol) of pyridine and 4.83 g (48.2 mmol) of butyl vinyl ether in 75 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. The mixture... | CCCCOC=CC(=O)C(F)(Cl)C(F)(F)F | null | null | null |
1,657,697 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH2:5]2.[N:15]1([C:20]([C:22]2[CH:23]=[N:24][CH:25]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:27]=2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[N:15]1([C:20]([C:22]2[CH:27]=[C:26]([C:2]3[CH:3]=[C:4]4[C:9](=... | CC1(C)OB(c2cncc(C(=O)N3CCCC3)c2)OC1(C)C | NC(=O)N1CCCc2cc(Br)cnc21 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 90 | null | To a mixture of 6-bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (55 mg, 0.22 mmol) and pyrrolidin-1-yl-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-methanone (78 mg, 0.26 mmol) in 1,4-dioxane (2 mL) is added 2.0 N aqueous sodium carbonate solution (0.23 mL, 0.46 mmol). Argon gas is ... | NC(=O)N1CCCc2cc(-c3cncc(C(=O)N4CCCC4)c3)cnc21 | null | 46.6 | null |
480,750 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [F:1][C:2]1[C:10]2[S:9][C:8]([C:11](=O)[CH2:12][C:13](=O)[CH:14]([F:16])[F:15])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[S:20]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1)(=[O:23])(=[O:22])[NH2:21]>>[F:1][C:2]1[C:10]2[S:9][C:8]([C:11]3[N:30]([C:27]4[CH:26]=[CH:25][C:24]([S:20]([NH2:21])(=[O:23])=[O:22])... | NNc1ccc(S(N)(=O)=O)cc1 | O=C(CC(=O)C(F)F)c1nc2cccc(F)c2s1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The procedure of Example 9 was repeated using 1-(7-fluorobenzothiazol-2-yl)-4,4-difluorobutane-1,3-dione and 4-sulfamoylphenylhydrazine hydrochloride as the starting materials to obtain 4-[5-(7-fluorobenzothiazol-2-yl)-3-difluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide (yield, 49%). | NS(=O)(=O)c1ccc(-n2nc(C(F)F)cc2-c2nc3cccc(F)c3s2)cc1 | null | 49 | null |
932,537 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)O1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH:28]=[C:27](OS(C(F)(F)F)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH:26]=[C:27]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:28][CH2:29]... | CC1(C)OB(c2ccc(N)cc2)OC1(C)C | CC(C)(C)OC(=O)N1CC=C(OS(=O)(=O)C(F)(F)F)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by Suzuki coupling of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine with 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (Synthesis, 993, (1991)) according to the procedure in Example 35, step (b). Mass spectrum (ESI, m/z): Calcd. f... | CC(C)(C)OC(=O)N1CC=C(c2ccc(N)cc2)CC1 | null | null | null |
935,001 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:59]=[CH:58][C:5]([CH2:6][CH:7]2[N:12]3[C:13](=[O:53])[CH:14]([NH:28][C:29]([CH:31]4[CH2:35][CH2:34][CH2:33][N:32]4C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)=[O:30])[CH2:15][N:16]([S:17]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=4[Cl:27])(=[O:19])=[O:18])[CH:11]3[CH2:10][N:9]([CH:54]([CH3:56])[CH3:55])[... | CC(C)N1CC2N(C(=O)C(NC(=O)C3CCCN3C(=O)OCC3c4ccccc4-c4ccccc43)CN2S(=O)(=O)c2ccc(Cl)cc2Cl)C(Cc2ccc(Cl)cc2)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCNCC | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 50 mg (0.089 mmol) of 3-amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione, 1 ml of DCM, 23 mg (0.178 mmol) of DIEA and 32 mg (0.090 mmol) of Fmoc-Pro-Cl was stirred at room temperature for 1 hour. The mixture was purified by chromatography on 2... | CC(C)N1CC2N(C(=O)C(NC(=O)C3CCCN3)CN2S(=O)(=O)c2ccc(Cl)cc2Cl)C(Cc2ccc(Cl)cc2)C1=O | null | 67.1 | null |
1,741,117 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[C:16]3[N:17]=[CH:18][N:19]=[C:20]([C:21]4[CH:26]=[C:25]([CH:27]([F:29])[F:28])[CH:24]=[CH:23][C:22]=4[O:30][CH2:31][CH:32]4[CH2:34][CH2:33]4)[C:15]=3[NH:14][C:13]=2[CH3:35])=[O:11])[CH2:5][C@@H:4]1[CH3:36].[C:37](Cl)(=[O:39])[CH3:38]>>[C:37]([NH:2][C@H:3]1[CH... | CC(=O)Cl | Cc1[nH]c2c(-c3cc(C(F)F)ccc3OCC3CC3)ncnc2c1C(=O)N[C@H]1CC[C@H](N)[C@@H](C)C1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from N-[(1S*,3S*,4S*)-4-amino-3-methylcyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide hydrochloride (example D.f65) and commercially available acetyl chloride the title compound is obtained as colorless solid. | CC(=O)N[C@H]1CC[C@H](NC(=O)c2c(C)[nH]c3c(-c4cc(C(F)F)ccc4OCC4CC4)ncnc23)C[C@@H]1C | null | null | null |
927,903 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:14][CH2:13][CH2:12]1)[C:7](=[O:15])[C:6]([C:16]([NH:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])=[C:5]2[OH:27].C(O)(C(F)(F)F)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:12][CH2:13][CH2:14]1)[C:7](=[O:15])[C:6]([C:16]([NH:18][CH2:19]... | CC(C)(C)OC(=O)CNC(=O)C1=C(O)c2cc(Cl)ccc2C2(CCC2)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | 1,1-Dimethylethyl N-((6′-chloro-4′-hydroxy-2′-oxo-spiro[cyclobutane-1,1′-naphthalen]-3′-yl)carbonyl)glycinate (151 mg, 385 μmol) was stirred in TFA (1 mL, 13462 μmol) for 20 minutes. Water was added. The resulting precipitate was filtered and washed with water to give the desired product as a white solid (87 mg). MS (m... | O=C(O)CNC(=O)C1=C(O)c2cc(Cl)ccc2C2(CCC2)C1=O | null | 67.3 | null |
551,140 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [O:1]=[C:2]1[CH2:7][CH2:6][O:5][CH:4]([CH2:8][O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:3]1.[CH2:22](O)[CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.ClCCl>[O:24]1[C:2]2([CH2:7][CH2:6][O:5][CH:4]([CH2:8][O:9][S:10]([C:13]3[CH:18]=[CH:17][C:16]([N+:19... | O=C1CCOC(COS(=O)(=O)c2ccc([N+](=O)[O-])cc2)C1 | OCCO | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 4-Nitro-benzenesulfonic acid 4-oxo-tetrahydro-pyran-2-ylmethyl ester (0.5 g, 1.59 mmol), ethylene glycol (986 mg, 15.9 mmol) and p-toluene sulfonic acid (61 mg, 0.32 mmol) were refluxed in benzene (20 ml) for 20 hours. The solvent was removed in vacuo to afford a solid. The solid was dissolved in dichloromethane (30 ml... | O=[N+]([O-])c1ccc(S(=O)(=O)OCC2CC3(CCO2)OCCO3)cc1 | null | 101.9 | null |
1,088,824 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:9][CH:10]=2)[C:5]([OH:16])=[C:4]([C:17]([OH:19])=O)[N:3]=1.Cl.C([O:25][C:26](=[O:35])[C@H:27]([NH2:34])[CH2:28][O:29]C(C)(C)C)(C)(C)C>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH:13]([CH3:14])[CH3:15])=[CH:9][CH:10]=2)[C:5]([OH:16])=[C:4]([C... | CC(C)(C)OC[C@@H](N)C(=O)OC(C)(C)C | CC(C)Oc1ccc2c(Cl)nc(C(=O)O)c(O)c2c1 | 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 in analogy to Example A-2 e) and f) from 1-chloro-4-hydroxy-6-isopropoxy-isoquinoline-3-carboxylic acid (can be obtained according to U.S. Pat. No. 6,093,730, October 1998, Weidmann et al.) and (R)-2-amino-3-tert-butoxy-propionic acid tert-butyl ester hydrochloride; MS-(+)-ion: M+1=369.0 amu. | CC(C)Oc1ccc2c(Cl)nc(C(=O)N[C@H](CO)C(=O)O)c(O)c2c1 | null | null | null |
220,280 | ord_dataset-6cb04513a4a244c0b612b566096f4b3d | null | 1990-01-01T00:12:00 | true | Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[O:9][CH3:10].C([Li])CCC.[CH:16](=[O:25])[C:17]1[C:18]([O:23][CH3:24])=[CH:19][CH:20]=[CH:21][CH:22]=1.[Cl-].[NH4+]>O1CCCC1>[Br:8][C:4]1[C:3]([O:9][CH3:10])=[C:2]([CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[OH:25])[CH:7]=[CH:6][CH:5]=1 | COc1c(Br)cccc1Br | COc1ccccc1C=O | null | [Cl-] | [Li]CCCC | [NH4+] | 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 | -63 | null | 2,6-Dibromoanisole (138.0 g, 0.51 mol) was dissolved in 750 ml of tetrahydrofuran and the solution cooled to -63° C. Butyl lithium (319 ml of 1.6 M, 0.51 mol) was added slowly with stirring and the mixture stirred at -60° C. for 4.5 hours and then 69.4 g (0.51 mol) of o-anisaldehyde in 250 ml of tetrahydrofuran was add... | COc1ccccc1C(O)c1cccc(Br)c1OC | null | null | null |
628,456 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | C(Br)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([OH:20])(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[SH:14]>C(O)C.[OH-].[Na+]>[CH:2]([S:14][C:13]1[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=1[C:11]([OH:20])=[O:19])=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1 | O=C(O)c1ccccc1S | BrCC=Cc1ccccc1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 1.28 g (6.49 mmol) of cinnamyl bromide in 8 ml of ethanol at room temperature under an atmosphere of nitrogen was added a solution of 1 g (6.49 mmol) of thiosalicylic acid in 5.3 ml of 10% aqueous sodium hydroxide solution. The solution was stirred at room temperature for 16 hours and the solvent then ... | O=C(O)c1ccccc1SC=Cc1ccccc1 | null | 102.2 | null |
549,716 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [CH2:1]([O:8][CH2:9][C@@H:10]([OH:17])[CH2:11][C:12](OCC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>C(O)C>[CH2:1]([O:8][CH2:9][C@@H:10]([OH:17])[CH2:11][C:12]([NH:19][NH2:20])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | CCOC(=O)C[C@H](O)COCc1ccccc1 | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 5 | 1 | In a 100 ml flask were put 4.15 g (17.4 mmol) of ethyl (S)-4-benzyloxy-3-hydroxybutyrate (optical purity: 89%e.e.) prepared in Reference Example 2, 20 ml of ethanol, and 2.62 g (52.2 mmol) of hydrazine monohydrate in a nitrogen stream, and the mixture was heated under reflux for 20 hours. The reaction mixture was coole... | NNC(=O)C[C@H](O)COCc1ccccc1 | null | 74.3 | null |
176,639 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | [C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:11]([CH:14]([CH2:18][CH2:19][CH3:20])[C:15](Cl)=[O:16])[CH2:12][CH3:13]>>[CH2:11]([CH:14]([CH2:18][CH2:19][CH3:20])[C:15]([C:7]1[CH:8]=[C:2]([C:1]([OH:10])=[O:9])[C:3]([OH:4])=[CH:5][CH:6]=1)=[O:16])[CH2:12][CH3:13] | O=C(O)c1ccccc1O | CCCC(CCC)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound is prepared by a Friedel-Crafts reaction from salicylic acid and 2-propylpentanoyl chloride. The acid yield is 52%. The recrystallization is done in petroleum ether. The melting point is 118° C. | CCCC(CCC)C(=O)c1ccc(O)c(C(=O)O)c1 | null | 52 | null |
893,497 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | Br[C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1>C1(C)C(C)=CC=CC=1>[N+:15]([C:4]1[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[C:2]([C:5]2[CH:4]=[CH:3][CH:2]=[CH:7][N:6]=2)[CH:3]=1)([O-:17])=[O:16] | O=c1c([N+](=O)[O-])cc(Br)cn1-c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | 120 | 8 | 1.27 g of 5-bromo-3-nitro-1-phenyl-1,2-dihydropyridin-2-one, 2.38 g of 2-tri-n-butyl stannyl pyridine and 248 mg of tetrakistriphenylphosphine palladium were added to 20 ml of xylene, followed by stirring at 120° C. overnight in nitrogen atmosphere. The reaction mixture was purified by silica gel chromatography (ethyl ... | O=c1c([N+](=O)[O-])cc(-c2ccccn2)cn1-c1ccccc1 | null | 101.1 | null |
980,603 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5][N:4]=1)#[N:2].[C:18](OC)(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[SH:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:26]=[C:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[S:21][C:1]([C:3]2[CH:8]=[C:7]([CH2:... | CC(C)(C)OC(=O)CCc1ccnc(C#N)c1 | COC(=O)c1ccccc1S | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | tert-Butyl 3-(2-cyano-4-pyridyl)propionate (0.51 g, 2.2 mmol) and methyl thiosalicylate (0.55 g, 3.3 mmol) were dissolved in toluene (2 ml), and triethylamine (0.47 ml, 3.4 mmol) was added thereto. The mixture was refluxed for 8 hrs and subjected to a silica gel (30 g) column chromatography. The fractions eluted with h... | CC(C)(C)OC(=O)CCc1ccnc(-c2nc(=O)c3ccccc3s2)c1 | null | 69.1 | null |
1,308,694 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)[S:10][C:3]=12.[F:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[OH:26].C(=O)([O-])[O-].[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O>[F:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[O... | Clc1ccnc2cc(-c3nccs3)sc12 | O=[N+]([O-])c1ccc(O)c(F)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | c1ccc(Oc2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | 180 | null | To a suspension of 10 (194 mg, 0.77 mmol) in Ph2O (10 mL) was added 2-fluoro-4-nitrophenol (240 mg, 1.53 mmol) and potassium carbonate (425 mg, 3.08 mmol) and the reaction mixture was heated at 180° C. for 4 hrs. The reaction mixture was cooled to room temperature and diluted with EtOAc. The resultant solution was wash... | O=[N+]([O-])c1ccc(Oc2ccnc3cc(-c4nccs4)sc23)c(F)c1 | null | 66.1 | null |
1,446,440 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH3:1][Li].[CH:3]1([C:9]2[CH:10]=[N:11][O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>C1COCC1>[CH:3]1([C:9]2[CH:10]=[N:11][O:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([C:20]([OH:22])([CH3:1])[CH3:21])=[CH:18][CH:19]=2)[CH2:4][CH2:5][CH2:6][CH2:7]... | CC(=O)c1ccc(-c2oncc2C2CCCCC2)cc1 | [Li]C | 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 | 0.25 | Methyl lithium (159 μL, 1.6 M solution in Et2O, 0.25 mmol) was added dropwise to a solution of 1-(4-(4-cyclohexylisoxazol-5-yl)phenyl)ethanone obtained above (57 mg, 0.21 mmol) in THF (2 mL) at 0° C. After stirring for 15 min, another 100μL of the methyl lithium solution was added to the reaction mixture. After being s... | CC(C)(O)c1ccc(-c2oncc2C2CCCCC2)cc1 | null | null | null |
1,465,437 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:10]([CH:18]=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:21][NH:22][CH3:23]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:10]([CH2:18][N:22]([CH3:23])[CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3]... | CC(C)(C)OC(=O)N1CCN(S(C)(=O)=O)C(C=O)C1 | CNC | 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 | Reductive amination of 3-formyl-4-methanesulfonyl-piperazine-1-carboxylic acid tert-butyl ester (160 mg) with dimethylamine hydrochloride (67 mg) according to General Procedure C followed by an aqueous work-up and purification on silica gave 3-dimethylaminomethyl-4-methanesulfonyl-piperazine-1-carboxylic acid tert-buty... | CN(C)CC1CN(C(=O)OC(C)(C)C)CCN1S(C)(=O)=O | null | 91 | null |
1,617,818 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[CH:27]=[C:26](F)[N:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1.[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2... | Fc1cc2c(Nc3ccc(OCc4cccc(Cl)c4)c(Cl)c3)ncnc2cn1 | COc1ccc(CN)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 71.5 | 91 | A mixture of compound 201 (2.60 g, 6.27 mmol) and 4-methoxybenzylamine (8.24 mL, 62.7 mmol) in dry DMSO (15 mL) was stirred under a nitrogen atmosphere at 71-72° C. (bath temperature) for 91 h. It was partitioned in between ethyl acetate (500 mL) and water (300 mL). The ethyl acetate layer was separated and washed furt... | COc1ccc(CNc2cc3c(Nc4ccc(OCc5cccc(Cl)c5)c(Cl)c4)ncnc3cn2)cc1 | null | null | null |
1,434,559 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.[CH:11](O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]2[NH:9][CH:11]=[N:8][C:6]=2[CH:7]=1 | Cc1cc(Br)cc(N)c1N | O=CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 5-bromo-3-methyl-benzene-1,2-diamine (Maybridge, 3 g; 14.92 mmol) in formic acid (75 mL) was heated at reflux for 16 hours. Reaction mixture was concentrated under vacuum to give a brown oil. It was extracted by EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuu... | Cc1cc(Br)cc2nc[nH]c12 | null | 97 | null |
920,766 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [OH-].[Li+].C[O:4][C:5](=[O:23])[C:6]1[CH:11]=[C:10]([S:12](=[O:17])(=[O:16])[N:13]([CH3:15])[CH3:14])[N:9]=[C:8]([NH:18][C@H:19]([CH2:21][CH3:22])[CH3:20])[CH:7]=1>C1COCC1>[C@@H:19]([NH:18][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([S:12](=[O:17])(=[O:16])[N:13]([CH3:14])[CH3:15])[N:9]=1)[C:5]([OH:23])=[O:4])([CH2:21][CH3:22])... | CC[C@H](C)Nc1cc(C(=O)OC)cc(S(=O)(=O)N(C)C)n1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 8 | Add 1 N lithium hydroxide (11.4 mL, 11.4 mmol) to a solution of (S)-2-sec-butylamino-6-dimethylsulfamoyl-isonicotinic acid methyl ester (1.43 g, 4.54 mmol) and THF (10 mL) at 0° C. Stir the mixture overnight, acidify the solution to about pH =2 and concentrate solvent to one half volume. Partition the residue between e... | CC[C@H](C)Nc1cc(C(=O)O)cc(S(=O)(=O)N(C)C)n1 | null | null | null |
934,689 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].S(Cl)([Cl:27])(=O)=O>ClCCCl.CCOC(C)=O>[Cl:27][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:20]([F:21])([F:22]... | O=S(=O)(Cl)Cl | O=C(CCc1ccc(O)cc1)Nc1ccc(Cl)c(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 84 | null | To a solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-3-(4-hydroxyphenyl)propanamide (1.33 g, 3.89 mmol) in DCE was added sulfuryl chloride (4.28 mL, 4.28 mmol) slowly over 45 min. The reaction mixture was heated at 84° C. overnight and then additional sulfuryl chloride was added. After heating for 2 h, the reaction ... | O=C(CCc1ccc(O)c(Cl)c1)Nc1ccc(Cl)c(C(F)(F)F)c1 | null | 44.9 | null |
173,021 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | [Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH:25]=[N:24][C:23]3[C:22](=[O:26])[NH:21][C:20]([NH2:27])=[N:19][C:18]2=3)=[CH:12][CH:11]=1.O>C(O)(=O)C>[Br:1][C:25]1[N:17]([CH2:16][C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[C:18]2[N:19]=[C:20]([NH2:27])[NH:21][C:22](=[O:26])[C:23]=2[N... | O=C1CCC(=O)N1Br | Nc1nc2c(ncn2Cc2ccc(Cl)cc2)c(=O)[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | 25 | 20 | N-Bromosuccinimide (1.3 g, 7.3 mmol) is added to a suspension of 9-(4-chlorophenyl)methylguanine (1.5 g; 5.4 mmol), Example 3, in glacial acetic acid (100 ml) and the mixture is stirred for 20 hours at room temperature. The solution is poured into water (400 ml) and the resulting precipitate is filtered, washed with wa... | Nc1nc2c(nc(Br)n2Cc2ccc(Cl)cc2)c(=O)[nH]1 | null | null | null |
1,624,489 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[CH:8]1([CH2:11][N:12]2[CH:17]=[C:16]([C:18]3[C:23]([O:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=4[F:32])=[CH:22][N:21]=[C:20](S(C)(=O)=O)[N:19]=3)[CH:15]=[C:14]([CH3:37])[C:13]2=[O:38])[CH2:10][CH2:9]1>CN(C=O)C>[CH:8]1([CH2:11][N:12]2[C:13](=[O:38])[C:14]([CH3... | CS(N)(=O)=O | Cc1cc(-c2nc(S(C)(=O)=O)ncc2Oc2ccc(F)cc2F)cn(CC2CC2)c1=O | 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 | Methanesulfonamide (68 mg, 0.71 mmol), NaH (28 mg, 0.7 mmol, 60% in mineral oil) and the title compound from step 3 (80 mg, 0.18 mmol) in DMF (2 mL) were reacted in a similar manner as Example 152, step 6 to give the title compound (45.00 mg, yield: 54.4%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 8.81 (s, 1H), ... | Cc1cc(-c2nc(NS(C)(=O)=O)ncc2Oc2ccc(F)cc2F)cn(CC2CC2)c1=O | null | 54.1 | null |
1,493,624 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | I[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[CH3:18][S:19]([CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:21])=[O:20]>>[CH3:28][C:22]([S:19]([CH3:18])(=[O:20])=[O:21])([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17... | ICCc1ccc(COc2ccccc2)cc1 | CCOC(=O)C(C)S(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 | 1-(2-Iodoethyl)-4-(phenoxymethyl)benzene (960 mg, 2.84 mmol) and ethyl 2-(methylsulfonyl)propanoate (512 mg, 2.84 mmol) were converted to the title compound (1.17 g, 106%) containing minor solvent impurities following the general procedure of step 2 in Preparation 2 for the formation of compound (1). 1H NMR (400 MHz, C... | CCOC(=O)C(C)(CCc1ccc(COc2ccccc2)cc1)S(C)(=O)=O | null | 105.5 | null |
954,831 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH3:1][O:2][C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][C:6]([C:12]([NH2:14])=[O:13])=[CH:5][CH:4]=1.[NH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:12]([NH2:14])=[O:13])=[CH:7][C:8]=1[C:9]([NH:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=... | Nc1cccc2ncccc12 | COc1ccc(C(N)=O)cc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The captioned compound was synthesized from 6-methoxyisophthalamic acid and 5-aminoquinoline by the same procedure as in the manufacturing method described in step C of Example 1-3-1. | COc1ccc(C(N)=O)cc1C(=O)Nc1cccc2ncccc12 | null | null | null |
1,019,794 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH3:1][C:2]1([CH3:30])[N:6]([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][C:18]4[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][C:19]=4[CH:20]=3)[CH:13]=[CH:12][N:11]=2)[C:5](=[O:28])[NH:4][C:3]1=[O:29].[H][H]>CO.[Pd]>[CH3:1][C:2]1([CH3:30])[N:6]([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][C:18]4[CH... | CC1(C)C(=O)NC(=O)N1CCNc1nccc(-c2cc3cc([N+](=O)[O-])ccc3s2)n1 | [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 | null | null | 5,5-Dimethyl-1-(2-(4-(5-nitrobenzothiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidine-2,4-dione (1.2 g, 2.82 mmol) was suspended in methanol (120 mL), 20% palladium on carbon (120 mg) was added, and the mixture placed on a Parr shaker under 50 psi of hydrogen gas for a total of 7 days. The reaction mixture was filter... | CC1(C)C(=O)NC(=O)N1CCNc1nccc(-c2cc3cc(N)ccc3s2)n1 | null | 26.8 | null |
799,045 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | [O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:16].[Na+]>CC(C)=O.CCCCCC>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][I:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | [I-] | ClCc1cccc(Oc2ccccc2)c1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | CCCCCC | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of 3-phenoxybenzyl chloride (10.0 g, 45.7 mmol) in 200 ml acetone was added sodium iodide (7.6 g, 507 mmol). The mixture was stirred at temperature overnight. The mixture was diluted with 300 ml hexane and the organic layer was washed twice with 5% sodium bicarbonate, once with brine and then dried over M... | ICc1cccc(Oc2ccccc2)c1 | null | null | null |
21,915 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8]CC)=[O:7])C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH2:23][CH2:22][CH2:21]2.[OH-].[Na+].C>O>[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:25]3[N:24]([CH:4]=[C:5]([C:6]([OH:8])=[O:7])[C:11]2=[O:13])[CH2:23][CH2:22][CH2:21][C:20]=3[CH:19]=1 | CCOC=C(C(=O)OCC)C(=O)OCC | COc1ccc2c(c1)CCCN2 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 220 | null | Diethyl ethoxymethylenemalonate (43.2 g., 0.20 mole) and 6-methoxytetrahydroquinoline (32.6 g., 0.20 mole) are mixed and heated at 125°-130° C. for three hours. Polyphosphoric acid (200 g.) is added, and the mixture is heated gradually to 220° C. then maintained at 220° C. for one hour. The mixture containing the produ... | COc1cc2c3c(c1)c(=O)c(C(=O)O)cn3CCC2 | null | null | null |
794,033 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [CH2:1]([C@H:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:5]([O:7]C)=[O:6])[CH:2]=[CH2:3].S(=O)(=O)(O)O>P([O-])([O-])([O-])=O>[CH2:1]([C@H:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:5]([OH:7])=[O:6])[CH:2]=[CH2:3] | C=CC[C@H](CCCCCC)C(=O)OC | null | null | O=P([O-])([O-])[O-] | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 40 | 77 | In a flask, there were placed 50 ml of 100 mM phosphate buffer (pH 6.0), 6 g of Novozyme CALB L (product of Novozyms) and 2 g of methyl (S)-2-allyloctanoate (60% ee) prepared in Example 31. After tight closure, the flask was shaken at 40° C. for 77 hours. To the mixture was added 0.35 ml of a 55% (w/w) aqueous solution... | C=CC[C@H](CCCCCC)C(=O)O | null | 65.1 | null |
1,473,895 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH:23]4[CH2:25][CH2:24]4)=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH2:26]([O:33][CH2:34][N:35]1[C:39](=[O:40])[CH:38]([CH3:41])[NH:37][C:36]1=[O:42])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH... | Cc1cc(C2CC2)cnc1N1CCN(C(=O)c2ccc(Br)cc2)CC1 | CC1NC(=O)N(COCc2ccccc2)C1=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 | Using (4-bromophenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (320 mg) described in Preparation Example 185 and 3-benzyloxymethyl-5-methylimidazolidine-2,4-dione (225 mg) described in Preparation Example 206 and by the reaction and treatment in the same manner as in Example 536, the title compoun... | Cc1cc(C2CC2)cnc1N1CCN(C(=O)c2ccc(N3C(=O)N(COCc4ccccc4)C(=O)C3C)cc2)CC1 | null | 64.6 | null |
700,730 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C([O:13][C:14](=O)[C:15]([C:28]#[N:29])=[CH:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([Br:27])[CH:18]=1)C>>[C:28]([C:15]1[C:14](=[O:13])[O:9][C:5]2[C:6]([C:16]=1[C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[... | CN(C)c1cccc(O)c1 | CCOC(=O)C(C#N)=Cc1cc(Br)c(OC)c(OC)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 3-dimethylaminophenol and 3-(3-bromo-4,5-dimethoxyphenyl)-2-cyano-acrylic acid ethyl ester by a procedure similar to that described for Example 16 in 0.5% yield. 1H NMR (CDCl3): 7.21-7.18 (m, 2H), 6.98 (d, J=1.8 Hz, 1H), 6.62 (dd, J=2.4, 9 Hz, 1H), 6.53 (d, J=2.7 Hz, 1H), 3.96 (s, 3... | COc1cc(-c2c(C#N)c(=O)oc3cc(N(C)C)ccc23)cc(Br)c1OC | null | 0.5 | null |
12,561 | ord_dataset-a0071d97083e4e69ae8872417ed2776b | null | 1976-01-01T00:09:00 | true | C[Li].[OH:3][C:4]1[C:9]2[C:10](=[O:24])[C:11]3[C:16]([C:17]4([CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]4)[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.Cl.[C:26](=O)([O-])[O-].[Na+].[Na+]>CCOCC.O>[OH:3][C:4]1[C:9]2[C:10]([OH:24])([CH3:26])[C:11]3[C:16]([C:17]4([CH2:18][CH2:19][N:20]([CH3:23])[CH2:2... | O=C([O-])[O-] | CN1CCC2(CC1)c1ccccc1C(=O)c1c(O)cccc12 | null | Cl | [Li]C | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | O | null | null | null | null | null | null | null | null | null | null | 1 | Methyl lithium in ether (5 ml., 1.5M) is added dropwise with stirring under nitrogen to 4-hydroxy-1'-methyl-10-oxo-9,10-dihydroanthracene-9-spiro-4'-piperidine (0.7 g.) in dry ether (25 ml.) and the mixture is stirred for 1 hour then diluted with water, acidified (2N hydrochloric acid), basified with sodium carbonate, ... | CN1CCC2(CC1)c1ccccc1C(C)(O)c1c(O)cccc12 | null | null | null |
36,949 | ord_dataset-3e699bae9dce4a0f996c34a7c5a4b79a | null | 1978-01-01T00:02:00 | true | [CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[CH:7]([OH:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].[C:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].[NH2-].[Li+]>CCCCCCC>[C:15]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:10][CH:7]2[CH2:6][C:5]([CH2:12][CH3:13])([... | COC(=O)c1ccc(C(C)(C)C)cc1 | CCC1(C)CC(O)C(C)C(C)(CC)N1 | null | [Li+] | [NH2-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | 15.0 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidinol (Compound 1) and 16.0 g of methyl p-t-butylbenzoate were dissolved in 500 ml of heptane. 1.5 g of lithium amide were then added to the solution and the mixture was refluxed by heating in a flask equipped with a Dean-Stark separator. 1.5 g of methanol were first remove... | CCC1(C)CC(OC(=O)c2ccc(C(C)(C)C)cc2)C(C)C(C)(CC)N1 | null | 104.2 | null |
573,733 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [CH3:1][S:2][C:3]1[S:7][C:6]([C:8]#[N:9])=[CH:5][C:4]=1[C:10]1[S:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1.O.[NH2:22][NH2:23]>CCO>[NH:22]([C:8]([C:6]1[S:7][C:3]([S:2][CH3:1])=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:5]=1)=[NH:9])[NH2:2... | CSc1sc(C#N)cc1-c1nc(-c2ccccc2)cs1 | 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 | 5-Methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carbonitrile (100 mg, 0.32 mmol) as prepared in previous step was dissolved in EtOH (10 mL). To this solution hydrazine monohydrate (10 eq) was added and the mixture was heated at reflux for 3 h. The EtOH solution was concentrated down to 1 mL and water (2 mL) was ... | CSc1sc(C(=N)NN)cc1-c1nc(-c2ccccc2)cs1 | null | 45 | null |
312,485 | ord_dataset-abe42048f0b84fa88446cee56a31e967 | null | 1995-01-01T00:07:00 | true | [CH3:1][NH:2][CH2:3][CH2:4][CH:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2.[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[CH2:23]>C(O)C>[CH:16]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=3[C:6](=[CH:5][CH2:4][CH2:3][N:2]([CH2:23][... | CNCCC=C1c2ccccc2C=Cc2ccccc21 | 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 | A mixture of 2.61 g of 5-[3-(methylamino)propylidene]-5H-dibenzo[a,d]cycloheptene, 1.20 g of ethyl acrylate, and 13 ml of ethanol was refluxed for 2 hours. After reaction was completed, the solvent was removed by distillation and the residue was purified by column chromatography on aluminum oxide [n-hexane-diethyl ethe... | CCOC(=O)CCN(C)CCC=C1c2ccccc2C=Cc2ccccc21 | null | null | null |
36,514 | ord_dataset-3e699bae9dce4a0f996c34a7c5a4b79a | null | 1978-01-01T00:02:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[NH:15][C:16]([NH:18][C:19]([O:21][CH3:22])=[O:20])=[S:17].[C:23](Cl)(=[O:25])[CH3:24]>O1CCCC1>[C:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[NH:15][C:16]([NH:18][C:1... | COC(=O)NC(=S)Nc1cc(Sc2ccccc2)ccc1N | CC(=O)Cl | 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 | 2 | 0.7 G. of 2-amino-1-(3-methoxycarbonyl-2-thioureido)-5- phenylthiobenzene, as prepared according to Example XI, is dissolved in 20 ml. tetrahydrofuran and treated with 1.5 ml. of acetyl chloride. The mixture is stripped after two hours and the residue recrystallized from methanol, yielding 2-acetamido-1-(3-methoxycarbo... | COC(=O)NC(=S)Nc1cc(Sc2ccccc2)ccc1NC(C)=O | null | null | null |
738,308 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [C:1]([C:3]1[CH:32]=[CH:31][C:6]([CH2:7][NH:8][C:9](=[O:30])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH:27]=[O:28])=[CH:16][C:15]=2[F:29])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CCO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:30])[CH:10]([C:1... | CCOC(C(=O)NCc1ccc(C#N)cc1)c1c(F)cc(-c2ccccc2C=O)cc1F | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a suspension of (RS)-N-(4-cyano-benzyl)-2-(3,5-difluoro-2′-formyl-biphenyl-4-yl)-2-ethoxy-acetamide (500 mg) in EtOH (1.2 ml) at 0° C. was added sodium borohydride (91 mg). After 5 min the ice bath was removed. Ice water was added and the mixture was extracted with EtOAc. The organic phase was dried, filtered and co... | CCOC(C(=O)NCc1ccc(C#N)cc1)c1c(F)cc(-c2ccccc2CO)cc1F | null | 82.2 | null |
1,617,653 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [CH3:1][O:2][N:3]([CH3:14])[C:4]([CH:6]1[CH2:9][CH:8]([CH2:10][C:11]([OH:13])=O)[CH2:7]1)=[O:5].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[F:37][C:38]([F:48])([F:47])[C:39]1[CH:40]=[C:41]([NH2:46])[C:42]([NH2:45])=[CH:43][CH:44]=1>C(Cl)Cl>[NH2:45][C:42]1[CH:43]=[CH:44][C:39]([C:38]([F:37])([F:47])[F:48])=[CH:40][C:41]=1[... | Nc1ccc(C(F)(F)F)cc1N | CON(C)C(=O)C1CC(CC(=O)O)C1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 0.33 | TEA (1.49 ml, 10.70 mmol) was added to a suspension of 2-{3-[methoxy(methyl)carbamoyl]cyclobutyl}acetic acid, EDC.HCl 1.18 g, 6.20 mmol), HOBt.xH2O (0.77 g, 5.69 mmol) in DCM (20 ml) at 0° C. and stirred for 5 min before the addition of 4-(trifluoromethyl)benzene-1,2-diamine (1.04 g, 10.34 mmol). This was stirred for a... | CON(C)C(=O)C1CC(CC(=O)Nc2cc(C(F)(F)F)ccc2N)C1 | null | 44 | null |
503,331 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:17]1N2CN3CN(C2)CN1C3.C(OCC)(=O)C>C(O)(=O)C>[N:1]1[CH:2]=[C:3]2[N:4]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=13)[S:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17]2 | CCOC(=O)CSc1cccc2nccn12 | C1N2CN3CN1CN(C2)C3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of ethyl (imidazo[1,2-a]pyridin-5-ylthio)acetate (11.8 g) in acetic acid (120 ml) was added hexamethylenetetramine (14.0 g) and the mixture was reacted at 90° C. for 10 hours. After this reaction mixture was allowed to cool, ethyl acetate (360 ml) was added and the mixture was washed with water. The organ... | CCOC(=O)C1=Cc2cnc3cccc(n23)S1 | null | 78.1 | null |
921,843 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | Cl.[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([F:33])[CH:24]=2)[CH2:19][CH2:18][NH:17][CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:34][N:35]=[C:36]=[O:37]>>[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:... | CN=C=O | Fc1cc(CO[C@H]2CCNC[C@H]2C(c2ccccc2)c2ccccc2)cc(C(F)(F)F)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The compound obtained in Example 26 (28.8 mg) and methyl isocyanate (6.8 mg) were reacted and treated in the same manner as in the method described in Example 31 to obtain the title compound. | CNC(=O)N1CC[C@H](OCc2cc(F)cc(C(F)(F)F)c2)[C@H](C(c2ccccc2)c2ccccc2)C1 | null | null | null |
1,047,960 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]3[CH:18]=[C:19]([Cl:26])[C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:16]=3[N:15]=[C:14]2[C:27]([NH2:30])([CH3:29])[CH3:28])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[C:31](Cl)(=[O:33])[CH3:32].O>ClCCl>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:... | CC(=O)OCCc1ccc(-n2c(C(C)(C)N)nc3cc(C(F)(F)F)c(Cl)cc32)cc1 | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 7 | To a solution of 2-{4-[2-(1-amino-1-methylethyl)-6-chloro-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetate (step 3, 121 mg, 0.27 mmol) in dichloromethane (5 ml) was added acetyl chloride (0.02 ml, 0.3 mmol). The reaction mixture was stirred at room temperature for 7 h. To the reaction mixture was added wat... | CC(=O)NC(C)(C)c1nc2cc(C(F)(F)F)c(Cl)cc2n1-c1ccc(CCOC(C)=O)cc1 | null | 58.4 | null |
340,031 | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | null | 1996-01-01T00:09:00 | true | [C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[N:9]1[C:17]([CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])=[N:18][N:19]=[C:8]1[C:7](=[O:27])[NH:6]2)#[N:2].[OH-].[Na+].Cl>>[C:22]([CH2:21][CH2:20][C:17]1[N:9]2[C:10]3[C:5]([NH:6][C:7](=[O:27])[C:8]2=[N:19][N:18]=1)=[CH:4][C:3]([C:1]#[N:2])=[C:12]([... | CCOC(=O)CCc1nnc2c(=O)[nH]c3cc(C#N)c(C(F)(F)F)cc3n12 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A mixture of 0.5 g (~1.3 mmol) of 7-cyano-1-(2-ethoxycarbonylethyl)-8-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one and 25 ml of 1N sodium hydroxide was stirred at 25° C. for 2 h. The solution was cooled in an ice bath and acidified with 4N hydrochloric acid to pH=2. The precipitate was filtered off to give... | N#Cc1cc2[nH]c(=O)c3nnc(CCC(=O)O)n3c2cc1C(F)(F)F | null | 63.5 | null |
1,471,065 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [CH3:1][N:2]([CH2:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]2[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][C:12]=12)C(=O)OC(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][NH:2][CH2:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]2[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3... | CN(Cc1cncc2c1ccn2COCC[Si](C)(C)C)C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A solution of tert-butyl methyl((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)carbamate (232 mg, 0.593 mmol) in DCM (20 mL) and TFA (10 mL) was stirred at RT for 3 h. The reaction mixture was quenched with water (100 mL) and extracted with DCM (50 mL×3). The combined extracts were dried (Mg... | CNCc1cncc2c1ccn2COCC[Si](C)(C)C | null | 76.4 | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.