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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
682,381 | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | null | 2005-01-01T00:08:00 | true | [CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH2:23][CH2:22][C:21]([C:30]([O:32]C)=[O:31])=[CH:20][C:19]=3[CH:34]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:... | CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)OC)CCN3CCCOC)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 50 | 15 | To a solution of methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(3-methoxypropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (362.3 mg) in a mixture of THF-methanol (5-10 ml) was added 1N sodium hydroxide solution (2.8 ml) at room temperature, and the mixture was stirred at 50° C. for 15 hours. After concentration under reduced... | CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)O)CCN3CCCOC)cc1 | null | 80.5 | null |
701,932 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])=[CH:10][C:9]=1[NH2:22])([CH3:4])([CH3:3])[CH3:2].CC1(C)[O:30][C:29]([C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=2)[C:34]#[N:35])=[CH:28][C:27](=O)[O:26]1>>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=... | CC(C)(C)OC(=O)Nc1ccc(-c2cc(F)ccc2F)cc1N | CC1(C)OC(=O)C=C(c2cccc(C#N)c2)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from (3-amino-2′,5′-difluoro-biphenyl-4-yl)-carbamic acid tert.-butyl ester (Example G45) (160 mg, 0.5 mmol) and 3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile (Example J4) (115 mg, 0.5 mmol) according to the general procedure K. Obtained as an amorphous white substance (110 mg). | CC(C)(C)OC(=O)Nc1ccc(-c2cc(F)ccc2F)cc1NC(=O)CC(=O)c1cccc(C#N)c1 | null | null | null |
187,840 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | Cl[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[CH:10]([C:12]1[CH:13]=[C:14]([Mg]Br)[CH:15]=[CH:16][CH:17]=1)=[CH2:11]>>[CH:2]([C:4]1[CH:9]=[C:8]([CH:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11])[CH:7]=[CH:6][CH:5]=1)=[CH2:3] | CC(Cl)c1ccccc1 | C=Cc1cccc([Mg]Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (1-Chloroethyl)benzene (formula VI) is subjected to coupling reaction with a Grignard reagent of 3-vinylphenylmagnesium bromide (formula VII) in the presence of a catalyst of nickel chloride (II)-diphosphine complex, to obtain 1-(3-vinylphenyl)-1-phenylethane. The reaction is carried out in a nitrogen atmosphere under ... | C=Cc1cccc(C(C)c2ccccc2)c1 | null | null | null |
1,071,146 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [C:1]([NH:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C[O-].[Na+]>CO>[C:1]([NH:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=3)=[CH:14][NH:15]2)=[CH... | CC(C)(C)NS(=O)(=O)c1ccc2cc[nH]c2c1 | O=C1CCCCC1 | 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 | 25 | 12 | To a solution of N-tert-butyl-1H-indole-6-sulfonamide (3.60 g, 14.2 mmol) and cyclohexanone (4.50 ml, 43.4 mmol) in methanol (72 ml) was added 28% sodium methoxide in methanol solution (17 ml), and the mixture was stirred for 12 hr with heating under reflux. The reaction mixture was cooled to room temperature and conce... | CC(C)(C)NS(=O)(=O)c1ccc2c(C3=CCCCC3)c[nH]c2c1 | null | 59.7 | null |
160,704 | ord_dataset-e402405fd21e4770a14f157cb62ca439 | null | 1987-01-01T00:07:00 | true | [CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[N+:7]([O-])([OH:9])=[O:8].S(=O)(=O)(O)O>>[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[N+:7]([O-:9])=[O:8] | Cc1c[nH]cn1 | O=[N+]([O-])O | null | 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 | 100 | 2 | 4-Methylimidazole (10 g, 0.12 moles), was cooled in a flask, and fuming nitric acid (11 ml, 0.24 moles) was added dropwise. This was followed by the addition of sulfuric acid (11 ml). The reaction was then heated with stirring at 100° C. for 21/2 hours. The cooled reaction mixture was then added to 500 ml of ice water,... | Cc1nc[nH]c1[N+](=O)[O-] | null | 41.6 | null |
395,070 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | CN(CCN(C)C)C.C([Li])(C)(C)C.[CH3:14][C:15]1([CH3:63])[O:19][C:18]2[C:20]([C:29]([C:47]3[C:57]4[O:58][C:59]([CH3:62])([CH3:61])[O:60][C:56]=4[CH:55]=[C:49]4[O:50][C:51]([CH3:54])([CH3:53])[O:52][C:48]=34)([C:31]3[C:41]4[S:42][C:43]([CH3:46])([CH3:45])[S:44][C:40]=4[CH:39]=[C:33]4[S:34][C:35]([CH3:38])([CH3:37])[S:36][C:... | CC1(C)Oc2cc3c(c(C(O)(c4c5c(cc6c4OC(C)(C)O6)OC(C)(C)O5)c4c5c(cc6c4SC(C)(C)S6)SC(C)(C)S5)c2O1)OC(C)(C)O3 | O=C=O | null | CN(C)CCN(C)C | [Li]C(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCCCC1 | CCOCC | null | null | null | null | null | null | null | null | null | null | 0.33 | Dry TMEDA (1.21 mL, 8.04 mmol) and t-butyllithium (5.36 mL, 1.5M in pentane) were dissolved in dry cyclohexane (12 mL) at 0° C. Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(2,2,6,6-tetramethyl benzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl)methanol (0.608 g, 0.804 mmol) was then added at ambient tem... | CC1(C)Oc2c(c(C(O)(c3c4c(c(C(=O)O)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)O)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c(c2C(=O)O)OC(C)(C)O3)O1 | null | null | null |
824,938 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | C=O.[F:3][C:4]([F:31])([F:30])[C:5]1[CH:29]=[CH:28][C:8]2[NH:9][C:10]3[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=3[N:12]=[C:13]([N:14]3[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH2:21][O:22][CH3:23])[CH2:15]3)[C:7]=2[CH:6]=1.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[F:31][C:4]([F:30])([F:3])[C:5]1[CH:29]=[CH:28][C:... | COCC[C@H]1CN(C2=Nc3ccccc3Nc3ccc(C(F)(F)F)cc32)CCN1 | CC(=O)O[BH-](OC(C)=O)OC(C)=O | null | C=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 0.03 | Add aqueous 37% formaldehyde (1.1 equiv.) to a solution of (S)-2-trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine (470 mg) in dichloroethane (0.2M). Stir the mixture 2 minutes and add sodium triacetoxyborohydride (1.5 equiv). Stir the suspension for 30 minutes and quench with a satu... | COCC[C@H]1CN(C2=Nc3ccccc3Nc3ccc(C(F)(F)F)cc32)CCN1C | null | 81 | null |
1,518,368 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=O.[CH2:13]([O:15][C:16](=[O:37])[CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:14]>C1C=CC=CC=1>[CH2:13]([O:15][C:16](=[O:37])/[CH:17]=[CH:11]/[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=2)[NH:7][CH:6]=1)[CH3:14] | Cc1ccc2[nH]cc(C=O)c2c1 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 80 | null | 5-methyl-1H-indole-3-carbaldehyde (900 mg, 5.65 mmol) was dissolved in benzene (100 ml), and ethyl(Triphenylphosphoranylidene)acetate (2954.1 mg, 8.48 ml) was drop-wise added. The temperature of mixture was raised to 80° C. and stirred under reflux for 12 hr. After completion of the reaction, the reaction mixture was c... | CCOC(=O)/C=C/c1c[nH]c2ccc(C)cc12 | null | 95 | null |
1,569,457 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([C:8]2[N:9]=[C:10]([CH3:16])[S:11][C:12]=2C(O)=O)[CH:7]=1.BrC1SC([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=C(C2C=C(Cl)C=CC=2OC)N=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([C:8]2[N:9]=[C:10]([CH3:16])[S:11][C:12]=2[NH:34][C:35](=[O:... | COc1ccc(Cl)cc1-c1nc(C)sc1C(=O)O | COc1ccc(Cl)cc1-c1nc(Br)sc1NC(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using 4-(5-chloro-2-methoxyphenyl)-2-methylthiazole-5-carboxylic acid, the title compound was prepared following the synthetic procedures described for tert-butyl 2-bromo-4-(5-chloro-2-methoxyphenyl)thiazol-5-ylcarbamate to give tert-butyl 4-(5-chloro-2-methoxyphenyl)-2-methylthiazol-5-ylcarbamate. LCMS (ESI) m+H=355.3... | COc1ccc(Cl)cc1-c1nc(C)sc1NC(=O)OC(C)(C)C | null | null | null |
1,546,268 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:13])[CH:5]=1)(=[O:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[C:17]([C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH:18]=[C:19]([Cl:21])[CH:20]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:16]=[C:17]([C:22]([OH:27])([C:23]([F:24])([F:25])[F:26])[CH2:2][C:1]([C:4]... | CC(=O)c1ccc(C(=O)O)c(C)c1 | O=C(c1cc(Cl)cc(Cl)c1)C(F)(F)F | 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 | 60 | 13 | 4.46 g of 4-acetyl-2-methylbenzoic acid, 6.08 g of 3′,5′-dichloro-2,2,2-trifluoroacetophenone, 18.2 g of toluene and 3.79 g of triethylamine were fed and the mixture was stirred for 13 hours at 60° C. 12.2 g of toluene was added to the slurry-state reaction solution, and the mixture was cooled to room temperature. The ... | Cc1cc(C(=O)CC(O)(c2cc(Cl)cc(Cl)c2)C(F)(F)F)ccc1C(=O)O | null | null | null |
1,325,533 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10](OC)=O.[NH:14]1C2=NC=CC=C2C=C1CN>>[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][NH2:14] | COC(=O)c1cc2ncccc2[nH]1 | NCc1cc2cccnc2[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Intermediate I was prepared from methyl 1H-pyrrolo[3,2-b]pyridine-2-carboxylate (1-1) following similar procedures for synthesizing intermediate H, as described above. MS (m/z): 148 (M+1)+. | NCc1cc2ncccc2[nH]1 | null | null | null |
625,423 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [F:1][C:2]([F:14])([F:13])[C@@:3]([O:8][Si](C)(C)C)([CH3:7])[C:4](Cl)=[O:5].[C:15]([NH:18][C:19]1[C:20]([Cl:34])=[C:21]([CH:23]=[CH:24][C:25]=1[S:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[NH2:22])(=[O:17])[CH3:16]>C(Cl)Cl.C(N(CC)CC)C>[C:15]([NH:18][C:19]1[C:20]([Cl:34])=[C:21]([NH:22][C:4](=[O:5])[C@:3]... | C[C@@](O[Si](C)(C)C)(C(=O)Cl)C(F)(F)F | CC(=O)Nc1c(Sc2ccc(F)cc2)ccc(N)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | A solution of (S)-3,3,3-trifluoro-2-(trimethylsilyloxy)-2-methylpropanoyl chloride (prepared from (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid (Method 25) as described in J. Med. Chem., 1999, 42, 2741-2746) (1.179 g) in DCM (10 ml) was added dropwise to a stirred and ice-cooled suspension of 3-acetamido-2-chlor... | CC(=O)Nc1c(Sc2ccc(F)cc2)ccc(NC(=O)[C@@](C)(O)C(F)(F)F)c1Cl | null | 57.9 | null |
1,421,353 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | C(OC(=O)[NH:10][C:11]([C:14](=[O:34])[NH:15][C:16]1[S:17][C:18]([C:25](=[O:33])[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[C:19]([C:21]([F:24])([F:23])[F:22])[N:20]=1)([CH3:13])[CH3:12])C1C=CC=CC=1.Br>C(O)(=O)C.[OH-].[K+]>[NH2:10][C:11]([CH3:13])([CH3:12])[C:14]([NH:15][C:16]1[S:17][C:18]([C:25](=[O:33])[C:... | CC(C)(NC(=O)OCc1ccccc1)C(=O)Nc1nc(C(F)(F)F)c(C(=O)c2ccc(F)cc2)s1 | null | null | Br | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of {1-[5-(4-Fluoro-benzoyl)-4-trifluoromethyl-thiazol-2-ylcarbamoyl]-1-methyl-ethyl}-carbamic acid benzyl ester (1.42 g, 2.79 mmol) and 33% HBr (in acetic acid, 5 mL, 92 mmol) in acetic acid (10 mL) was stirred at RT for 1 h, diluted with aqueous KOH carefully to make pH=8-9, and the product was extracted wit... | CC(C)(N)C(=O)Nc1nc(C(F)(F)F)c(C(=O)c2ccc(F)cc2)s1 | null | null | null |
130,176 | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | null | 1985-01-01T00:05:00 | true | Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][C:14](=[O:16])[O:13][C:12]([CH3:18])([CH3:17])[C:11]=2[CH:19]=1.[C:20]([C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21]>>[C:20]([C:24]1[CH:25]=[CH:26][C:27]([S:30][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:8]=[CH:9][... | CC1(C)OC(=O)Nc2ccc(OCCCCCl)cc21 | CC(C)(C)c1ccc(S)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 1 from 6-(4-chlorobutoxy)-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4-tert.butyl-thiophenol. | CC(C)(C)c1ccc(SCCCCOc2ccc3c(c2)C(C)(C)OC(=O)N3)cc1 | null | null | null |
224,549 | ord_dataset-1d5bba1436bd42b7a27c43833c25d871 | null | 1991-01-01T00:03:00 | true | C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[CH2:19]([C:22]1([CH:29]=[O:30])[CH2:27][CH:26]2[CH2:28][CH:23]1[CH:24]=[CH:25]2)[CH:20]=[CH2:21]>CCCCCC.C1COCC1>[CH2:19]([C:22]1([CH:29]([OH:30])[CH:10]([C:9]2[CH:16]=[CH:17][CH:18]=[C:7]([Cl:6])[CH:8]=2)[N:11]2[... | C=CCC1(C=O)CC2C=CC1C2 | Clc1cccc(Cn2ccnc2)c1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | -70 | 0.5 | 13.8 ml (20 mmol) of a 1.45 molar solution of n-butyllithium in hexane were added dropwise to a solution of 3.85 g (20 mmol) of 1-(3-chlorobenzyl)-imidazole in 40 ml of absolute THF at -70° C. After stirring for 30 minutes at -70° C., a solution of 4.39 g of 74% purity (20 mmol) 2-allyl-5-norbornen-2-aldehyde in 30 ml ... | C=CCC1(C(O)C(c2cccc(Cl)c2)n2ccnc2)CC2C=CC1C2 | null | 38 | null |
1,681,746 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH2:3]1.CCN(CC)CC.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([N:7]1[CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH:2]1[CH3:1])(=[O:25])[CH3:24] | CC1CN(c2ccc(C=O)cc2)CCN1 | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 0.33 | A solution of 4-(3-methylpiperazin-1-yl)benzaldehyde (1.0 g, 4.89 mmol) in methylene chloride (15 mL) was cooled to 0° C. and treated with Et3N (0.68 mL, 4.89 mmol), followed by acetyl chloride (0.34 mL, 4.89 mmol). The resulting solution was stirred at 0° C. for 20 minutes and then concentrated in vacuo. The material ... | CC(=O)N1CCN(c2ccc(C=O)cc2)CC1C | null | 73.1 | null |
273,608 | ord_dataset-ee287d49cb8642e59ae9c3951f746312 | null | 1993-01-01T00:08:00 | true | C1(C2C=CC(C([O:13][C@@H:14]3[CH2:21][C@H:20]4[C@H:16]([CH2:17][C:18](=[O:22])[O:19]4)[C@H:15]3/[CH:23]=[CH:24]/[C@@H:25]([O:33][CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][O:35]3)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=O)=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:13][C@@H:14]1[CH2:21][C@H:20]2[C@H:1... | CCCCCCC[C@@H](/C=C/[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1OC(=O)c1ccc(-c2ccccc2)cc1)OC1CCCCO1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 6 | The tetrahydropyranyl ether (5) (5.03 g) was dissolved into a dry methanol (300 ml), into which potassium carbonate (1.49 g) was added, and stirred at room temperature for 6 hours. A crude compound obtained by a usual work-up was column-chromatographed to give the title compound (6). Yield: 3.25 g. | CCCCCCC[C@@H](/C=C/[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1O)OC1CCCCO1 | null | null | null |
479,242 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Cl[C:7]1[N:8]=[C:9]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:10]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:11]=2[N:12]=1>>[N:1]1([C:7]2[N:8]=[C:9]([NH:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C:10]3[C:15]4[CH2:16][CH... | Fc1ccc(CNc2nc(Cl)nc3sc4c(c23)CCCC4)cc1 | c1cn[nH]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 | Following the procedure of Example 97, the reaction of pyrazole with 2-chloro-5,6,7,8-tetrahydro-4-(4-fluorobenzylamino)-[1]-benzothieno-[2,3-d]-pyrimidine gives 2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(4-fluorobenzylamino)-[1]-benzothieno-[2,3-d]-pyrimidine. | Fc1ccc(CNc2nc(-n3cccn3)nc3sc4c(c23)CCCC4)cc1 | null | null | null |
1,194,494 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | C([O:3][C:4](=[O:14])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)=[O:6])C.[OH-].[K+].Cl>CO>[Br:13][C:9]1[CH:8]=[C:7]([C:5](=[O:6])[C:4]([OH:14])=[O:3])[CH:12]=[CH:11][CH:10]=1 | CCOC(=O)C(=O)c1cccc(Br)c1 | null | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (1 g, 3.9 mmol) in methanol (10 mL) was added potassium hydroxide (2 mL, 50% w/v in water) and the resulting mixture was stirred at room temperature for 30 minutes. Hydrochloric acid (1 N) was added to adjust to pH 4. The mixture was extracted with ethyl ace... | O=C(O)C(=O)c1cccc(Br)c1 | null | 89 | null |
1,319,851 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [OH-].[Na+].O1CCOCC1.[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(=O)C>[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][C:18]=1[C:... | COC(=O)c1cc(N2CCCCC2)ccc1OCc1ccccc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 1 | A 4 mol/L aqueous solution of sodium hydroxide (9.8 mL) was added to a dioxane (45 mL) solution of the obtained methyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate (4.3 g), followed by stirring at room temperature for 1 hour and then at 50 to 55° C. for 2 hours. After cooling the reaction mixture to room temperature, the r... | O=C(O)c1cc(N2CCCCC2)ccc1OCc1ccccc1 | null | 89.9 | null |
1,499,334 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2([C:11]#N)[CH2:10][CH2:9][CH2:8]2)=[C:4](I)[CH:3]=1.C([Li])(C)(C)C.C1C[O:24]CC1>>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([CH2:6][C:7]3([CH2:10][CH2:9][CH2:8]3)[C:11]2=[O:24])=[CH:4][CH:3]=1 | C1CCOC1 | N#CC1(Cc2ccc(Br)cc2I)CCC1 | null | [Li]C(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | -78 | 1.5 | A dried flask charged with 1-(4-bromo-2-iodobenzyl)cyclobutanecarbonitrile (Intermediate 37, 2.60 g, 6.91 mmol), was dissolved in dry THF (100 mL) under an argon atmosphere. The resulting mixture was cooled to −78° C. and then was tert-butyllithium (1.7 M in pentane, 8.13 mL, 13.83 mmol), added dropwise. The reaction w... | O=C1c2cc(Br)ccc2CC12CCC2 | null | 63 | null |
650,710 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:18]3[CH:26]=[CH:27][C:28]([C:30]#[N:31])=[CH:29][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12... | C[Sn](C)(C)N=[N+]=[N-] | N#Cc1ccc2c(c1)nc(-c1ccc(OCc3ccccc3)cc1)n2C1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 48 | A suspension of compound 12 (0.041 g, 0.10 mmol) and trimethyltin azide (0.023 g, 0.11 mmol) in toluene (2 mL) was refluxed for 15 h. The reaction mixture was allowed to stand at rt for 48 h. The resulting suspension was filtered and washed with toluene (2×). The solid was treated with hydrogen chloride (4 M in dioxane... | c1ccc(COc2ccc(-c3nc4cc(-c5nnn[nH]5)ccc4n3C3CCCCC3)cc2)cc1 | null | 20 | null |
869,197 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Br[C:14]1[CH:15]=[CH:16][C:17]([CH:20]([F:22])[F:21])=[N:18][CH:19]=1>>[F:21][CH:20]([F:22])[C:17]1[N:18]=[CH:19][C:14]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)=[CH:15][CH:16]=1 | FC(F)c1ccc(Br)cn1 | O=C(O)c1ccc(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 | Operations similar to those of Production Example 14 were conducted using 4-carboxyphenylboronic acid and 5-bromo-2-(difluoromethyl)pyridine, to provide the title compound as white solid. | O=C(O)c1ccc(-c2ccc(C(F)F)nc2)cc1 | null | null | null |
1,683,508 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[C:14]1([CH2:20][CH2:21][C@H:22]([OH:25])[C:23]#[CH:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C(Cl)Cl>[C:6]([Si:10]([CH3:12])([CH3:11])[O:25][C@@H:22]([CH2:21][CH2:20][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:23]#[CH:24])([CH3:9])([CH3... | C#C[C@@H](O)CCc1ccccc1 | CC(C)(C)[Si](C)(C)Cl | null | Cl | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 14 | Following a procedure of Noyori (Suzuki, M. et al., J. Med. Chem. 41, 3084-3090 (1998)); Imidazole (919.1 mg, 13.5 mmol, 1.8 eq.) and t-butylchlorodimethylsilane (1.35 g, 9.0 mmol) were added to a solution of (S)-5-phenylpent-1-yn-3-ol 86 (1.2 g, 7.5 mmol, 1 eq.) in CH2Cl2 (18 ml), cooled to 0° C. The reaction mixture ... | C#C[C@H](CCc1ccccc1)O[Si](C)(C)C(C)(C)C | null | null | null |
504,182 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | C([O:5][C:6]([C@H:8]([C@@H:18]([CH2:54][CH:55]([CH3:57])[CH3:56])[C:19]([NH:21][N:22]([CH2:50][CH:51]([CH3:53])[CH3:52])[C:23](=[O:49])[C@@H:24]([CH2:43][O:44]C(C)(C)C)[NH:25][C:26]([O:28][CH2:29][CH:30]1[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])=[O:20])[CH2:9]/... | CC(C)C[C@@H](C(=O)NN(CC(C)C)C(=O)[C@@H](COC(C)(C)C)NC(=O)OCC1c2ccccc2-c2ccccc21)[C@H](C/C=C/c1ccccc1)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 | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 2.5 | A solution of 1.05 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethyloxycarbonyl)-O-tert.butyl-D-seryl]-4-methylvalerohydrazide in 5 ml of dichloromethane was treated at room temperature under nitrogen with 5 ml of trifluoroacetic acid. The mixture was stirred at room tem... | CC(C)C[C@@H](C(=O)NN(CC(C)C)C(=O)[C@@H](CO)NC(=O)OCC1c2ccccc2-c2ccccc21)[C@H](C/C=C/c1ccccc1)C(=O)O | null | 86.7 | null |
1,411,687 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | COC1C=CC(C[NH:8][CH:9]2[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][C:10]2([CH3:20])[CH3:19])=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:19][C:10]1([CH3:20])[CH:9]([NH2:8])[CH2:18][CH2:17][C:12]2([O:13][CH2:14][CH2:15][O:16]2)[CH2:11]1 | COc1ccc(CNC2CCC3(CC2(C)C)OCCO3)cc1 | null | null | [Pd+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 2 | N-(4-Methoxybenzyl)-7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-amine (2.3 g, 7.54 mmol, 1 eq) was dissolved in MeOH (30 ml); Pd(OH)2 (690 mg) was added, and hydrogenation was carried out for 2 h at RT under balloon pressure (H2). After monitoring by thin-layer chromatography, the reaction mixture was filtered off over Cel... | CC1(C)CC2(CCC1N)OCCO2 | null | 72 | null |
203,576 | ord_dataset-76a008eb2d3f48d891cad325041f3d1e | null | 1990-01-01T00:02:00 | true | [O:1]([CH3:10])[CH:2]1[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[CH2:3]1.[C:11]1([C:17](Cl)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO>N1C=CC=CC=1>[C:17]([O:9][CH2:8][C@H:6]1[O:7][CH:2]([O:1][CH3:10])[CH2:3][C@@H:4]1[OH:5])([... | COC1C[C@H](O)[C@@H](CO)O1 | ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 72 | To a solution of 11.2 g (0.07 mole) of methyl 2-deoxyribofuranoside (90% pure) in 60 ml of dry pyridine under a dry nitrogen atmosphere were added 19.0 g (0.07 mole) of triphenylmethyl chloride. The mixture was stirred at ambient temperature for three days. Methanol (35 ml) was then added. The solvents were then evapor... | COC1C[C@H](O)[C@@H](COC(c2ccccc2)(c2ccccc2)c2ccccc2)O1 | null | null | null |
1,092,508 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][NH:27][C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.Br[C:42]1[CH:57]=[CH:56... | COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4)cn2)cc1 | Cc1cc(C(=O)NCc2cccnc2)ccc1Br | null | null | null | null | null | null | null | 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 bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (70 mg) and 4-bromo-3-methyl-N-pyridin-3-ylmethyl-benzamide (60 mg) instead of 4-chloropicolinic acid t-butylamide, in the same manner as Example 1-D-07, a crude product of 4-(4-{2-[bis-(4-methoxy-benzyl... | COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4c3ccc(C(=O)NCc4cccnc4)cc3C)cn2)cc1 | null | null | null |
1,715,090 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | Cl.C[O:3]C(=O)[C@H](CCC(OC)=O)N.COC(=O)[C@H](CCC(OC)=O)NN[C:20](=[O:38])[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:23][C:22]=1[N+:35]([O-:37])=[O:36]>>[C:31]([O:30][C:28]([NH:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([OH:38])=[O:3])=[C:22]([N+:35]([O-:37])=[O:36])[CH:2... | COC(=O)CC[C@H](N)C(=O)OC | COC(=O)CC[C@H](NNC(=O)c1ccc(NC(=O)OC(C)(C)C)cc1[N+](=O)[O-])C(=O)OC | 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 synthesis was achieved in analogy to example 2 by using L-glutamic acid-dimethylester-hydrochloride instead of the L-glutamic acid-di-tert.-butylester-hydrochloride. From 14.8 g of 4-(tert-butoxycarbonylamino)-2-nitrobenzoic acid 27.4 g of crude dimethyl-N-(4-(tert.-butoxycarbonylamino)-2-nitrobenzamido)-L-glutamat... | CC(C)(C)OC(=O)Nc1ccc(C(=O)O)c([N+](=O)[O-])c1 | null | null | null |
1,456,351 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Br-].[CH3:2][C:3]1[C:16]2[NH2+:15][C:14]3[C:9](=[CH:10][C:11]([Br:17])=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=[C:5](Br)[CH:4]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C(Cl)(Cl)Cl>[Br-:17].[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:5]2[CH:4]=[C:3]([CH3:2])[C:16]3[C:7]([CH:6]=2)=[S+:8][C:9]2[C:14](=[CH:13][C... | CN1CCNCC1 | Cc1cc(Br)cc2c1[NH2+]c1ccc(Br)cc1S2 | null | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 3 | To a solution of 1-methyl-3,7-dibromophenothiazinium bromide (300 mg, 0.7 mmol) in chloroform (15 mL) kept under argon, 1-methylpiperazine (350 mg, 3.5 mmol) was added (30 min) with vigorous stirring. The mixture was stirred for 3 h and after that extracted once with aqueous HBr (10 mL, 1% v/v) and twice with water. Th... | Cc1cc(N2CCN(C)CC2)cc2[s+]c3cc(N4CCN(C)CC4)ccc3nc12 | null | null | null |
608,853 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[C:11]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[CH2:3][CH2:2]1.Br[CH2:27][CH2:28][CH2:29][C:30]([CH2:44][CH3:45])([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:31][C:32]([O:34][CH:35]([CH3:37... | CCC(CCCBr)(CC(=O)OC(C)C)c1ccccc1 | O=C(NC1CCNCC1)c1ccccc1-c1ccc(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 | Prepared from 4′-trifluoromethyl-biphenyl-2-carboxylic acid-piperidin-4-ylamide and isopropyl 5-bromo-2-ethyl-2-phenyl-pentanecarboxylate. | CCC(CCCN1CCC(NC(=O)c2ccccc2-c2ccc(C(F)(F)F)cc2)CC1)(CC(=O)OC(C)C)c1ccccc1 | null | null | null |
904,307 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:25])=[C:9]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])... | COc1ccc(-c2cccc3c2c(C)c(-c2ccccc2)n3Cc2ccccc2)cc1 | null | null | BrB(Br)Br | 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 | The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 1-benzyl-4-(4-methoxy-phenyl)-3-methyl-2-phenyl-1H-indole (1.029 g, 2.550 mmol) was reacted with BBr3 (3.1 ml of a 1M solution in CH2Cl2) to give the product (0.657 g, 1.687 mmol, 66%) as a white solid, mp 174-176° C. 1H NMR (DMSO-... | Cc1c(-c2ccccc2)n(Cc2ccccc2)c2cccc(-c3ccc(O)cc3)c12 | null | null | null |
1,705,685 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Cl:1][C:2]1[C:6]([NH:7][CH2:8][CH:9]2[CH2:11][CH2:10]2)=[CH:5][N:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1.[O:18]=[C:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:24][C:25](O)=[O:26].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[C:6]([N:7]([CH2:8][CH:9]2[CH2:11][CH2:10]2)[C:25](=[O:26])[CH2:24][N:20]2... | Clc1nn(-c2cccnc2)cc1NCC1CC1 | O=C(O)CN1CCCC1=O | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To a 7 mL vial was added 3-chloro-N-(cyclopropylmethyl)-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.124 g, 0.500 mmol) (prepared according to the U.S. Publication No. 2012/0110702), DMAP (0.183 g, 1.50 mmol), 2-(2-oxopyrrolidin-1-yl)acetic acid (0.143 g, 1.00 mmol), EDCI (0.240 g, 1.25 mmol) followed by CH2Cl2 (1 mL). The r... | O=C1CCCN1CC(=O)N(CC1CC1)c1cn(-c2cccnc2)nc1Cl | null | null | null |
837,361 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [CH:1]1([O:6][N:7]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.NN.[N+:20]([C:23]1[CH:24]=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21].C(N(CC)C(C)C)(C)C>O1CCCC1>[CH:1]1([O:6][NH:7][S:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)(=[O:30])=[O:31])[CH2:2... | O=C1c2ccccc2C(=O)N1OC1CCCC1 | O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1 | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 2.5 | A mixture of 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione (3.00 g, 12.99 mmol) in anhydrous tetrahydrofuran (25 mL) under an Argon atmosphere was treated with anhydrous hydrazine (0.448 mL, 14.29 mmol). After stirring vigorously for 2.5 hours, the resulting slurry was filtered and washed with approximately 15 mL of an... | O=[N+]([O-])c1cccc(S(=O)(=O)NOC2CCCC2)c1 | null | 86.7 | null |
73,618 | ord_dataset-10f2568b472a4cabb35c3f313a159005 | null | 1980-01-01T00:11:00 | true | C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16]C=2)[CH:6]=[CH:7][CH:8]=1.Cl.N1C=CC=C[CH:22]=1>Cl.O>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:22])[CH:6]=[CH:7][CH:8]=1 | COc1cccc(CCCCCc2ccccc2)c1 | c1ccncc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 190 | null | A mixture of 2-(3-methoxyphenyl-5-phenylpentane (20 g.) and pyridine hydrochloride (94 g.) under nitrogen is heated to 190° C. for 2 hours with vigorous stirring. The reaction mixture is cooled, dissolved in 6 N hydrochloric acid (200 ml.) and diluted with water to 600 ml. The aqueous solution is extracted with ethyl a... | CC(CCCc1ccccc1)c1cccc(O)c1 | null | null | null |
202,614 | ord_dataset-19e5fc80c1554f4f8641c835e055f02b | null | 1990-01-01T00:01:00 | true | [OH-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([S:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=2)[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:4]=1.Cl>CO>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([S:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)[CH2:10][N:11]2[C... | COC(=O)c1ccc(SC(Cn2ccnc2)c2cccnc2)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 40 | 5 | 3.39 ml of a 1N aqueous solution of sodium hydroxide were added to 575 mg of methyl-4-[1-(3-pyridyl)-2-(imidazol-1-yl)ethylthio]benzoate (prepared as described in Example 45) in 7 ml of methanol, and the resulting mixture was stirred at 40° C. for 5 hours. At the end of this time, the resulting mixture was neutralized ... | O=C(O)c1ccc(SC(Cn2ccnc2)c2cccnc2)cc1 | null | 55.3 | null |
803,257 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [C:1]([NH:4][C:5]1[C:13]2[S:12][C:11]([NH2:14])=[N:10][C:9]=2[C:8]([O:15][CH3:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>>[C:1]([NH:4][C:5]1[C:13]2[S:12][C:11]([NH:14][C:22](=[O:23])[C:21]3[CH:25]=[CH:26][C:18]([F:17])=[CH:19][CH:20]=3)=[N:10][C:9]=2[C:8](... | COc1ccc(NC(C)=O)c2sc(N)nc12 | O=C(Cl)c1ccc(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 | Using 7-acetylamino-4-methoxy-benzothiazol-2-ylamine and 4-fluoro-benzoyl chloride the title compound was obtained as a tan solid (25% yield), MS: m/e=359.1 (M+H+). | COc1ccc(NC(C)=O)c2sc(NC(=O)c3ccc(F)cc3)nc12 | null | null | null |
1,115,280 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [Cl:1][C:2]1[C:3]([CH2:11][CH3:12])=[C:4]([NH2:10])[C:5]([CH2:8][CH3:9])=[CH:6][CH:7]=1.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[Cl:1][C:2]1[C:3]([CH2:11][CH3:12])=[C:4]([NH2:10])[C:5]([CH2:8][CH3:9])=[C:6]([N+:13]([O-:15])=[O:14])[CH:7]=1 | CCc1ccc(Cl)c(CC)c1N | O=[N+]([O-])O | null | 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 | 0 | 2.5 | 1.83 ml (10.9 mmol) 3-Chloro-2,6-diethyl-phenylamine (1) is dissolved on an ice-bath at 0° C. in 8 ml conc. H2SO4. 562 μl (12.0 mmol; 1.1 eq.) 90% ige HNO3 is added and the reaction mixture is stirred for 2.5 hours at 0° C. The reaction mixture is pored on ca. 200 ml ice and the obtained solution is extracted 8 times w... | CCc1c(Cl)cc([N+](=O)[O-])c(CC)c1N | null | 84.3 | null |
576,938 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | C(O[C:6]([NH:8][C@@H:9]1[CH2:13][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([N:27]([C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=3)=[O:32])[CH2:28][CH:29]=[CH2:30])[CH2:23][CH2:22]2)[CH2:10]1)=[O:7])(C)(C)C.[F:44][C... | O=C(Cl)c1ccc(F)cc1 | C=CCN(C(=O)OCc1ccc([N+](=O)[O-])cc1)C1CCN(C[C@H]2C[C@H](NC(=O)OC(C)(C)C)C[C@@H]2c2ccccc2)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 | Using essentially the same procedure as in Example 16, Step A and B but substituting 1-(R)-((t-butoxycarbonyl)amino)-3-(S)-((4-(N-(4-nitrobenzyloxycarbonyl)-N-(allyl)amino)piperidin-1-yl)methyl)-4-(S)-phenylcyclopentane from Example 34 in Step A and 4-fluorobenzoyl chloride in Step B, the title compound was prepared. | C=CCN(C(=O)OCc1ccc([N+](=O)[O-])cc1)C1CCN(C[C@H]2C[C@H](NC(=O)c3ccc(F)cc3)C[C@@H]2c2ccccc2)CC1 | null | null | null |
1,467,945 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [CH3:1][C@@:2]([S:30]([CH3:33])(=[O:32])=[O:31])([CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:29]=[N:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH:17]=[N:16]1)[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl>CCO>[OH:6][NH:5][C:3](=[O:4])[C@:2]([CH3:1])([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:13][CH2:14][N:15]1[CH... | C[C@@](CCn1cc(-c2cnc3ccccc3n2)cn1)(C(=O)NOC1CCCCO1)S(C)(=O)=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(quinoxalin-2-yl)-1H-pyrazol-1-yl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.685 g, 1.62 mmol, 1 eq) in EtOH (8 mL) was added 1M HCl (4 mL). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was concentrated and azeotroped with MeOH ... | C[C@@](CCn1cc(-c2cnc3ccccc3n2)cn1)(C(=O)NO)S(C)(=O)=O | null | 6 | null |
1,433,271 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | C([O:8][C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][C:34]=1[CH3:35])[C:12]([NH:14][C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:16]=1[O:30][CH3:31])=[O:13])C1C=CC=CC=1.[H][H]>CO.O1CCCC1.[Pd]>[C:21]([C:19]1[CH:18]=[C:17]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27]... | [H][H] | COc1c(NC(=O)c2ccc(C)c(OCc3ccccc3)c2)cc(C(C)(C)C)cc1NS(C)(=O)=O | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 7.10 g 3-benzyloxy-N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-benzamide are hydrogenated in a mixture of 70 ml of methanol and 40 ml of tetrahydrofuran in the presence of 800 mg palladium on activated charcoal (10% Pd) at ambient temperature and 50 psi partial hydrogen pressure. Then the catalys... | COc1c(NC(=O)c2ccc(C)c(O)c2)cc(C(C)(C)C)cc1NS(C)(=O)=O | null | null | null |
1,698,108 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Cl:1][C:2]1[C:7]([NH:8][C:9]2[N:14]=[C:13]([N:15]([CH2:25][CH3:26])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:12]3=[N:27][CH:28]=[C:29]([C:30]#[N:31])[N:11]3[N:10]=2)=[CH:6][C:5]([C:32]#[N:33])=[CH:4][C:3]=1[N:34]1[CH2:39][CH2:38][C@@H:37]([NH:40][C:41](=[O:44])[O:42][CH3:43])[C@H:36]([OH... | CC(C)(C)OP(=O)(OCCCC(=O)O)OC(C)(C)C | CCN(Cc1ccc(OC)cc1)c1nc(Nc2cc(C#N)cc(N3CC[C@@H](NC(=O)OC)[C@H](O)C3)c2Cl)nn2c(C#N)cnc12 | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a suspension of methyl ((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-hydroxypiperidin-4-yl)carbamate (100 mg, 0.158 mmol) and 4-((di-tert-butoxyphosphoryl)oxy)butanoic acid (141 mg, 0.475 mmol) in DCM (5 mL) at 0° C., was added DCC (98 mg, 0... | CCN(Cc1ccc(OC)cc1)c1nc(Nc2cc(C#N)cc(N3CC[C@@H](NC(=O)OC)[C@H](OC(=O)CCCOP(=O)(OC(C)(C)C)OC(C)(C)C)C3)c2Cl)nn2c(C#N)cnc12 | null | 50.1 | null |
633,394 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:13]2[CH2:18][CH:19]([CH3:21])[CH3:20])C1C=CC=CC=1>[C].[Pd]>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:13]2[CH2:18][CH:19]([CH3:21])[CH3:20] | CCOC(=O)c1cc2c(OCc3ccccc3)cccc2n1CC(C)C | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By the reactions in the same manner as in Starting Material Synthesis Example 10 using ethyl 4-benzyloxy-1-(2-methylpropyl)indole-2-carboxylate (6.0 g) and 10% palladium-carbon (0.6 g), the title compound was obtained as pale-brown crystals. | CCOC(=O)c1cc2c(O)cccc2n1CC(C)C | null | null | null |
1,253,650 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=O)[O:3][C:2]1=O.[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].COC(OC)OC>C1COCC1>[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([N:17]2[C:4](=[O:3])[C:5]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:1]=[CH:2]2)[CH:18]=[CH:19][CH:20]=1 | O=c1[nH]c2ccccc2c(=O)o1 | Cc1c(N)cccc1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | COC(OC)OC | null | null | null | null | null | null | null | null | null | 100 | null | A mixture of 1H-benzo[d][1,3]oxazine-2,4-dione (200 mg, 1.226 mmol), 3-bromo-2-methylaniline (228 mg, 1.226 mmol), and trimethoxymethane (390 mg, 3.68 mmol) in THF (2 mL) was heated overnight in a sealed tube at 100° C. The mixture was cooled to rt and concentrated, and the residue was purified by column chromatography... | Cc1c(Br)cccc1-n1cnc2ccccc2c1=O | null | 36.2 | null |
1,745,288 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [H-].[Na+].[CH3:3][C:4]1([CH3:11])[O:8][CH:7]([CH2:9][OH:10])[CH2:6][O:5]1.Br[C:13]1[N:14]=[CH:15][S:16][CH:17]=1>>[CH3:3][C:4]1([CH3:11])[O:8][CH:7]([CH2:9][O:10][C:13]2[N:14]=[CH:15][S:16][CH:17]=2)[CH2:6][O:5]1 | Brc1cscn1 | CC1(C)OCC(CO)O1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | NaH (60% dispersion in mineral oil, 12.19 g, 305.3 mmol) was added portionwise to DL-1,2-isopropylideneglycerol (16.11 g, 1218 mmol) and the mixture was stirred until gas evolution had ceased (ca. 30 min RT, followed by 2 h at 60° C.). Subsequently, 4-bromothiazole (20.00 g, 121.9 mmol) was added and the mixture was st... | CC1(C)OCC(COc2cscn2)O1 | null | null | null |
1,147,596 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[S:18][C:19]([S:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:29]([O:31]C)=[O:30])[C:24]=3[F:33])=[CH:20][N:21]=2)=[N:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH... | COC(=O)c1nccc(Sc2cnc(Nc3ccc(CNC(=O)OC(C)(C)C)cn3)s2)c1F | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | 2 | A solution of methyl 4-(2-(5-((tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinate (1.28 g, 2.60 mmol) in tetrahydrofuran (40 mL) was treated with sodium hydroxide (5N, 3.12 mL, 15.6 mmol) at 23° C. The reaction was stirred for 2 hours, then acidified with conc. HCl to pH ˜2.0. Water ... | CC(C)(C)OC(=O)NCc1ccc(Nc2ncc(Sc3ccnc(C(=O)O)c3F)s2)nc1 | null | 87 | null |
492,722 | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | null | 2001-01-01T00:02:00 | true | [F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si:13]([CH3:18])([CH3:17])[CH2:14][CH2:15]O>ClCCl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:15][CH2:14][Si:13]([CH3:18])([CH3:17])[CH3:12])=[O:5] | O=C(O)c1ccc(I)cc1F | C[Si](C)(C)CCO | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 23 | To a solution of 115.5 mg (0.4 mmol) of 2-fluoro-4-iodobenzoic acid (Compound B) in 10 mL of dichloromethane (under a blanket of argon) was added 91.5 mg (0.5 mmol) of 1-(3-dimethylaminopropyl-3-ethyl carbodiimide hydrochloride) and 53 mg (0.4 mmol) of 4-dimethylaminopyridine. To this reaction mixture was added 0.16 ml... | C[Si](C)(C)CCOC(=O)c1ccc(I)cc1F | null | null | null |
177,626 | ord_dataset-3ef78abb9a384506b240a419b70e6ceb | null | 1988-01-01T00:09:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][N:5](C)[CH2:4][CH2:3]1.Cl[C:10]([O:12][CH:13]([Cl:15])[CH3:14])=[O:11]>>[Cl:15][CH:13]([O:12][C:10]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:11])[CH3:14] | CC(Cl)OC(=O)Cl | CN1CCN(C)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In a similar manner, N,N'-di-methylpiperazine is reacted with α-chloroethyl chloroformate (ACE-Cl) to give the intermediate N-α-chloroethoxycarbonyl N'-methyl piperazine, which is then dehydrohalogenated as in Example 21b to give N-(vinyloxycarbonyl)N'-methylpiperazine. | CC(Cl)OC(=O)N1CCN(C)CC1 | null | null | null |
1,595,683 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]([C:5]1[N:6]=[C:7]([N:16]2[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][CH3:15])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(N2CCC(F)(F)C2)C2N=NNC=2N=1)(C)(C)C.BrCC[C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([Cl:52])[CH:47]=1>>[C:1]([C:5]1[N:6]=[C:7]([N:16]2[CH2:20][CH2:19][C:18]... | CCn1nnc2c(N3CCC(F)(F)C3)nc(C(C)(C)C)nc21 | Clc1cccc(CCBr)c1 | null | CC(C)(C)c1nc(N2CCC(F)(F)C2)c2nn[nH]c2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described for the synthesis of 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 61), the title compound was prepared from 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and 1-(2-bromoethyl)-3-chlorobenzene and... | CC(C)(C)c1nc(N2CCC(F)(F)C2)c2nnn(CCc3cccc(Cl)c3)c2n1 | null | null | null |
1,070,003 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [CH3:1][C:2]([CH3:27])([CH2:24][CH2:25][CH3:26])[CH2:3][O:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[C:10]([O:21]C)[N:11]2[CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:7]([NH2:23])[N:6]=1.Cl.[OH-].[Na+]>CO.O1CCOCC1>[NH2:23][C:7]1[N:6]=[C:5]([O:4][CH2:3][C:2]([CH3:1])([CH3:27])[CH2:24][CH2:25][CH3:26])[N:13]=[C:12... | CCCC(C)(C)COc1nc(N)c2nc(OC)n(CC3CCOCC3)c2n1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 2-[(2,2-dimethylpentyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (116 mg) in dry MeOH (14.5 mL) was added 4N HCl in 1,4-dioxane (2.48 mL). The mixture was stirred at room temperature for 3 h. The reaction was neutralised to pH 7 with 2M sodium hydroxide solution and was concent... | CCCC(C)(C)COc1nc(N)c2[nH]c(=O)n(CC3CCOCC3)c2n1 | null | 68 | null |
950,994 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:25])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(N(CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:25][C:26](=[O:28])[CH3:27])=[C:8]2[C:14]([Br:15])=[C:13](... | CCOC(=O)c1ncc2c(c1O)c(Br)c(Br)n2Cc1ccc(F)cc1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | Prepared in analogy to that of Example 120(a) from 2,3-dibromo-1-(4-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester, acetic anhydride, and triethyl amine. The title compound, ESI MS (m/z): 513 (M+H)+. | CCOC(=O)c1ncc2c(c(Br)c(Br)n2Cc2ccc(F)cc2)c1OC(C)=O | null | null | null |
728,643 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [CH3:1][N:2]([CH3:20])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[N:33]=[C:34]=[O:35])([CH3:23])[CH3:22]>>[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:3... | CC(C)c1cccc(C(C)C)c1N=C=O | CC(C)c1ccc(NCc2ccc(N(C)C)cc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By the reaction and treatment in the same manner as in Example 2 using [(4-dimethylaminophenyl)methyl](4-isopropylphenyl)amine (0.80 g) and 2,6-diisopropylphenyl isocyanate (0.72 g) as starting materials, N′-(2,6-diisopropylphenyl)-N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)urea (0.62 g) was obtained. | CC(C)c1ccc(N(Cc2ccc(N(C)C)cc2)C(=O)Nc2c(C(C)C)cccc2C(C)C)cc1 | null | 44.1 | null |
1,344,995 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [F:1][CH2:2][C:3]1([CH2:14][F:15])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:4]1=2.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:13][C:10]1[CH:11]=[CH:12][C:4]2[C:3]([CH2:14][F:15])([CH2:2][F:1])[O:7][B:6]([OH:8])[C:5]=2[CH:9]=1 | O=C1CCC(=O)N1Br | Cc1ccc2c(c1)B(O)OC2(CF)CF | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 3,3-bis(fluoromethyl)-6-methylbenzo[c][1,2]oxaborol-1(3H)-ol (0.5 g, 2.36 mmol) in CCl4 (10 mL) under nitrogen was added NBS (420 mg, 2.36 mmol) and BPO (57 mg, 0.236 mmol). The mixture was refluxed for 2 h under the light from a Sun lamp, and then it was cooled to rt, washed with aqueous NaHCO3 and br... | OB1OC(CF)(CF)c2ccc(CBr)cc21 | null | 87.4 | null |
148,372 | ord_dataset-0b70410902ae4139bd5d334881938f69 | null | 1986-01-01T00:09:00 | true | [C:1]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.[H+]>>[C:1]([C:5]1[CH:10]=[C:9]([S:11][CH:1]([S:11][C:9]2[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([OH:16])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=2)[CH:5]2[CH2:10][C... | CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O | null | null | F[B-](F)(F)F | [H+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2 | A solution of 10 grams of 2,6-di-tert-butyl-4-mercaptophenol and 2.3 grams of cyclohex-3-enyl carboxaldehyde is charged to a flame-dried flask and treated with 1.0 ml of tetrafluoroboric acid and stirred for two hours. The reaction mixture is extracted with aqueous sodium bicarbonate and dried over anhydrous magnesium ... | CC(C)(C)c1cc(SC(Sc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C2CC=CCC2)cc(C(C)(C)C)c1O | null | 113.1 | null |
1,179,572 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([F:26])[CH:20]=1)[CH3:16]>CC(C)=O>[CH2:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[C:21]([F:26])[CH:20]=1)[CH3:16] | CCOC(=O)c1ccc(O)c(F)c1 | BrCCCCBr | null | O=C([O-])[O-] | [I-] | [K+] | 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 | 1,4-Dibromobutane (2.34 g, 10.8 mmol), potassium carbon-ate (1.86 g, 13.5 mmol) and potassium iodide (90 mg, 0.5 mmol) were added to a solution of 3-fluoro-4-hydroxy-benzoic acid ethyl ester from Example E27 (11.0 g, 5.4 mmol) in acetone (25 ml) and the mixture was heated at reflux for 20 h. The solid was filtered off,... | CCOC(=O)c1ccc(OCCCCBr)c(F)c1 | null | 80 | null |
1,035,855 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([NH:11][C:12]1[C:17]([C:18](OCC)=[O:19])=[CH:16][N:15]=[C:14]([Cl:23])[CH:13]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([NH:11][C:12]1[CH:13]=[C:14]([Cl:23])[N:15]=[CH:16][C:17]=1[CH2:18][OH:19])([CH3:10])([CH3:8])[CH3:9] | CCOC(=O)c1cnc(Cl)cc1NC(C)(C)C | 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 | null | 0.33 | LiAlH4 ((2.1 g, 54.7 mmol) was added portion wise to a 0° C. solution of ethyl 4-(tert-butylamino)-6-chloronicotinate (7 g, 27.3 mmol) in THF (100 mL). After 20 min, the reaction was quenched by the addition of water (2.1 mL), followed by 2 N aq NaOH (2 N, 2.1 ml. The resulting suspension was filtered and the filtrate ... | CC(C)(C)Nc1cc(Cl)ncc1CO | null | 85.3 | null |
566,872 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | [O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([OH:13])=[O:12])[CH:8]=2)[NH:3]1.[O:14]=[C:15]1[C:20]2=[CH:21][NH:22][C:23]([CH:24]=O)=[C:19]2[CH2:18][CH2:17][NH:16]1.N1CCCCC1>C(O)C>[O:1]=[C:2]1[C:10](=[CH:24][C:23]2[NH:22][CH:21]=[C:20]3[C:19]=2[CH2:18][CH2:17][NH:16][C:15]3=[O:14])[C:9]2[C:4](=[CH:5][CH:6]... | O=Cc1[nH]cc2c1CCNC2=O | O=C1Cc2cc(C(=O)O)ccc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCNCC1 | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid (44.5 mg, 0.25 mmol), 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde (41 mg, 0.25 mmol) and 0.1 mL of piperidine in ethanol (1 mL) was heated in a sealed tube at 80° C. for 6 hours. The precipitate was collected by vacuum filtration, washed w... | O=C1Nc2ccc(C(=O)O)cc2C1=Cc1[nH]cc2c1CCNC2=O | null | 24.7 | null |
1,186,200 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [C:1]([C:3]1[CH:20]=[CH:19][C:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11][C:5]=2[CH:4]=1)#[N:2].Cl.[NH2:22][OH:23].C(=O)(O)[O-].[Na+]>C(O)C>[OH:23][NH:22][C:1](=[NH:2])[C:3]1[CH:20]=[CH:19][C:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:1... | CC(C)(C)OC(=O)N1CCc2ccc(C#N)cc2CC1 | NO | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 50 | 5 | A suspension of 1,1-dimethylethyl 7-cyano-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (may be prepared as described in WO2002040471) (5 g, 18.36 mmol), hydroxylamine hydrochloride (2.55 g, 36.7 mmol) and sodium bicarbonate (7.71 g, 92 mmol) in ethanol (250 ml) was heated at 50° C. overnight. Further hydroxylamine... | CC(C)(C)OC(=O)N1CCc2ccc(C(=N)NO)cc2CC1 | null | 92.6 | null |
1,004,202 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [OH:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1.Cl[CH2:17][C:18]1[N:19]=[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O>[C:23]1([C:20]2[S:21][CH:22]=[C:18]([CH2:17][O:1][C:2]3[CH:15]=[CH:14][C:5]4[CH:6... | ClCc1csc(-c2ccccc2)n1 | COC(=O)CC1COc2cc(O)ccc21 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 65 | 3 | Methyl (6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetate (200 mg, 0.961 mmol) and 4-(chloromethyl)-2-phenyl-1,3-thiazole (240 mg, 1.14 mmol) were dissolved in N,N-dimethylformamide (5 mL), and potassium carbonate (160 mg, 1.16 mmol) was added, and the mixture was stirred at 60-70° C. for 3 hr. Water was added to the rea... | COC(=O)CC1COc2cc(OCc3csc(-c4ccccc4)n3)ccc21 | null | 73.7 | null |
1,523,904 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH3:1][N:2]1[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]4[O:22][CH:6]5[C:7]([CH:9]=[CH:10][C@:11]2([OH:23])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8].C(O)(=O)C>[Pd].O>[CH3:1][N:2]1[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]4[O:22][C@H:6]5[C@@H:7]([OH:8])[CH2:9][CH2:10][... | COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | null | null | [Pd] | 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 | null | 0.83 | A mixture of dry 14-hydroxycodeinone (9.5 g dry) and damp 14-hydroxycodeinone (8.5 g by LOD) was charged to a reactor and triturated with water (150 g) (to enable blending) for 15 min. The resulting slurry was filtered and a sample of the cake dried at 50° C. under vacuum (0.39 g) for analysis. The remaining wet cake (... | COc1ccc2c3c1O[C@H]1[C@@H](O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | null | null | null |
1,630,083 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [C:1]([C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8](=[O:25])[C:9]4[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][C:10]=4[C:11]([CH3:17])([CH3:16])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1)#[N:2].[CH3:26][S:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])=[O:28]>>[CH3:26][S:27]([N:30]1[CH2:35][CH2:34][N:33]([C:22]([C:19]2... | CC1(C)c2cc(C(=O)O)ccc2C(=O)c2c1[nH]c1cc(C#N)ccc21 | CS(=O)(=O)N1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Under the same conditions as the method for synthesizing Compound B3-15, the title compound was prepared from Compound B2-28 and 1-methanesulfonylpiperazine. | CC1(C)c2cc(C(=O)N3CCN(S(C)(=O)=O)CC3)ccc2C(=O)c2c1[nH]c1cc(C#N)ccc21 | null | null | null |
201,649 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | [CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[CH:21]([NH:23][CH2:24][CH2:25][CH:26]1[O:31][CH2:30][CH2:29][NH:28][CH2:27]1)=[O:22]>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:28]4[CH2:29][CH2:30][O:31][CH:26]... | O=CNCCC1CNCCO1 | O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=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 | By the use of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 2-(2-formylaminoethyl)morpholine, the reaction is similarly carried out as Example 11 to give 1-cyclopropyl-6,8-difluoro-7-[2-(2-formylaminoethyl)morpholino]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. | O=CNCCC1CN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)CCO1 | null | null | null |
1,652,841 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[NH:8]1[CH2:11][CH:10]([C:12]2[CH:33]=[CH:32][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:29]([CH3:31])[CH3:30])[N:26]=[CH:27][N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1.[C:34]([OH:40])([C:36](F)(F)F)=[O:35].C(Cl)Cl>>[OH:3][C:2]([C:4]([F:7])([F:6]... | CC(C)n1ncnc1-c1nc2c(s1)CCOc1cc(C3CNC3)ccc1-2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | Following a similar procedure to 8-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt 235 using {3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-acetic acid tert-butyl ester and TFA:DCM (1:2), {3-[2-(2... | CC(C)n1ncnc1-c1nc2c(s1)CCOc1cc(C3CN(CC(=O)O)C3)ccc1-2 | null | null | null |
1,227,576 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | CC(C)([O-])C.[K+].[CH2:7]([N:14]([CH2:18][C:19]1[C:24](Cl)=[N:23][C:22]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]2[CH3:32])=[CH:21][N:20]=1)[CH2:15][CH2:16][OH:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>CN(C=O)C>[CH2:7]([N:14]1[CH2:18][C:19]2[N:20]=[CH:21][C:22]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH:2... | CC1CCCCN1c1cnc(CN(CCO)Cc2ccccc2)c(Cl)n1 | null | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of potassium tert-butoxide (0.65 g) in DMF (4 mL) was added dropwise a solution of 2-(benzyl{[3-chloro-5-(2-methylpiperidin-1-yl)pyrazin-2-yl]methyl}amino)ethanol (1.63 g) in DMF (4 mL) at 0° C., and the mixture was stirred for 2 hr. Water (10 mL) was added, and the mixture was extracted with ethyl acetat... | CC1CCCCN1c1cnc2c(n1)OCCN(Cc1ccccc1)C2 | null | 86.3 | null |
386,016 | ord_dataset-d330662edaed408d950898172aba7a4c | null | 1997-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[C:6](I)[C:5]2=[O:13].[NH:14]1[CH:18]=[CH:17][CH:16]=[N:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:14]1[CH:18]=[CH:17][C:16]([C:7]2[O:8][C:9]3[C:4]([C:5](=[O:13])[CH:6]=2)=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=3)=[N:15]1 | c1cn[nH]c1 | O=c1c(I)coc2ccc(Cl)cc12 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | null | A mixture of 6-chloro-3-iodochromone (153 mg) prepared in Example 28, pyrazole (136 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) was reacted at 80° C. for 2 hours with stirring. The reaction mixture was added to ice water and extracted from chloroform. The organic layer was dried over anhydrous sod... | O=c1cc(-c2cc[nH]n2)oc2ccc(Cl)cc12 | null | 34 | null |
556,907 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [CH2:1]1[O:12][C:11]2[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][C:3]=2[O:2]1.Cl[C:14]1[C:15]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[S:26][C:16]=2[N:17]=[C:18]([C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[N:19]=1>>[N:21]1[CH:22]=[CH:23][N:24]=[CH:25][C:20]=1[C:18]1[N:19]=[C:14]([NH:8][CH2:7][CH2:6][C:5]2[C... | NCCc1ccc2c(c1)OCO2 | FC(F)(F)c1cc2c(Cl)nc(-c3cnccn3)nc2s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | With the procedure of Example 1, the reaction of 3,4-methylenedioxyphenethylamine with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethyl-thieno-[2,3-d]-pyrimidine yields 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-trifluoromethyl-thieno-[2,3-d]-pyrimidine. | FC(F)(F)c1cc2c(NCCc3ccc4c(c3)OCO4)nc(-c3cnccn3)nc2s1 | null | null | null |
465,952 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | [C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C@H:16]2[CH2:21][CH2:20][CH2:19][C@H:18]([NH2:22])[CH2:17]2)[CH:13]=[CH:14][CH:15]=1.O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:1]([NH:22][CH:18]1[CH2:19][CH2:20][CH2:21][CH:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH3:8])[CH:11]=2)[CH2:17]1)(=[O:3])[CH3:2... | COc1cccc([C@H]2CCC[C@H](N)C2)c1 | CC(=O)OC(C)=O | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | c1ccncc1 | null | null | null | null | null | null | null | null | null | 50 | 2 | Acetic anhydride (1 ml) and pyridine (0.5 ml) were added to (trans)-3-(3-methoxyphenyl) cyclohexylamine (10 mg) and the mixture was stirred at 50° C. for 2 hours. The reaction solution was poured into glacial sodium bicarbonate water and extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric a... | COc1cccc(C2CCCC(NC(C)=O)C2)c1 | null | 53.3 | null |
489,681 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[N:34]1[CH:35]=[CH:36][N:37]2[C:42]([CH2:43][CH2:44]O)=[CH:41][CH:40]=[CH:39][C:38]=12.[C:46]([OH:49])(=[S:48])[CH3:47]>O1CCCC1.CN(C)C=O>[C:46]([S:48][CH2:44][CH2:43][C:42]1[N:37]2[CH:36]=[CH:35][N:34]=[C:38]2[CH:39]=[CH:40][CH:41]=1)(=[O:49])[CH3:47] | CC(O)=S | OCCc1cccc2nccn12 | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0.17 | To a solution of triphenyl phosphine (4.20 g) in tetrahydrofuran (30 ml) was added dropwise, at −15° C., diisopropyl azodicarboxylate (3.16 ml). The mixture was stirred for 10 minutes at the same temperature. To the reaction mixture were, then, added a solution of 2-(imidazo[1,2-a]pyridin-5-yl)ethanol (1.00 g) in dimet... | CC(=O)SCCc1cccc2nccn12 | null | null | null |
548,173 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | C(N1CCCC(N([C:21]2[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=2)[C:24]([N:26](CC)CC)=[O:25])C2C=CC=CC=2)C1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[C:24]([NH2:26])(=[O:25])[C:23]1[CH:31]=[CH:32][CH:33]=[CH:21][CH:22]=1 | CCN(CC)C(=O)c1cccc(N(c2ccccc2)C2CCCN(Cc3ccccc3)C2)c1 | null | null | [Pd+2] | [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 | null | null | A solution of 3-[N-(1-benzyl-piperidin-3-yl)-anilino]-N,N-diethyl benzamide (compound 17) (50 mg, 0.11 mmol) in EtOH (5 mL) was hydrogenated at 30 psi in the presence of a catalytic amount of Pd(OH)2 on carbon for 6 h. The mixture was filtered through Celite®, concentrated and the residue purified by chromatography (gr... | NC(=O)c1ccccc1 | null | 112.6 | null |
1,055,202 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([O:17][C@H:18]2[CH2:22][CH2:21][O:20][CH2:19]2)[CH:16]=1)[C:5]([NH:7][C:8]1[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=1)=[O:6].[Si]([O:30][CH2:31][CH2:32][N:33]([CH3:45])[C:34](=[O:44])[C:35]1[CH:40]=[CH:39][C:38](F)=[C:37]([Cl:42])[C:36]=1F)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].O>C... | Cn1ccc(NC(=O)c2cc(O)cc(O[C@H]3CCOC3)c2)n1 | CN(CCO[Si](C)(C)C(C)(C)C)C(=O)c1ccc(F)c(Cl)c1F | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | 140 | null | A mixture of 3-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide (539 mg, 1.77 mmol), N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-chloro-2,4-difluoro-N-methylbenzamide (539 mg, 1.77 mmol) and potassium carbonate (490 mg, 3.55 mmol) in acetonitrile (15 mL) was placed in a Smith Creator mic... | CN1CCOc2c(ccc(Oc3cc(O[C@H]4CCOC4)cc(C(=O)Nc4ccn(C)n4)c3)c2Cl)C1=O | null | 31.9 | null |
1,473,324 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [F:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.Cl.[CH:13]1([C:16]2[C:17]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:18][CH:19]=[C:20]([CH3:22])[CH:21]=2)[CH2:15][CH2:14]1>>[CH:13]1([C:16]2[C:17]([N:23]3[CH2:28][CH2:27][N:26]([C:6]([C:5]4[CH:4]=[N:3][C:2]([F:1])=[CH:10][C:9]=4[CH3:11])=[... | Cc1cnc(N2CCNCC2)c(C2CC2)c1 | Cc1cc(F)ncc1C(=O)O | 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 | Using 6-fluoro-4-methylnicotinic acid (139 mg) and a free form (210 mg) of 1-(3-cyclopropyl-5-methylpyridin-2-yl)piperazine hydrochloride described in Preparation Example 85 with a base and by the reaction and treatment in the same manner as in Preparation Example 119, the title compound (180 mg) was obtained. | Cc1cnc(N2CCN(C(=O)c3cnc(F)cc3C)CC2)c(C2CC2)c1 | null | 61.4 | null |
1,574,409 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)#N.C(O)(=[O:33])C>N1C=CC=CC=1.[Ni].O>[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C@H:10]([NH:23][C:24](=[O:30])... | CC(=O)O | COc1ccc(N(C)C(=O)[C@H](Cc2cccc(C#N)c2)NC(=O)OC(C)(C)C)cc1 | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 46 | 8 | (S)-tert-Butyl 3-(3-cyanophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (2.7 g, 6.60 mmole) was dissolved in pyridine (18.6 ml) and acetic acid (9.3 ml). Raney Nickel (2.7 g of a slurry in H2O) was added and the resulting suspension was stirred at 46° C. overnight. The reaction was confirmed compl... | COc1ccc(N(C)C(=O)[C@H](Cc2cccc(C=O)c2)NC(=O)OC(C)(C)C)cc1 | null | null | null |
1,264,600 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [C:1]1([C:7]2[CH2:8][CH2:9][N:10]([C:13](Cl)=[O:14])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21]C(=O)C1C=CC=CC=1>>[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:13]([N:10]1[CH2:11][CH:12]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1)=[O:14] | O=C(NCCCCO)c1ccccc1 | O=C(Cl)N1CC=C(c2ccccc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Phenyl-3,6-dihydro-2H-pyridine-1-carboxylic acid (4-hydroxybutyl)amide (62B) is prepared from 62A as described for 1D. The product is obtained in almost quantitative yield. | O=C(NCCCCO)N1CC=C(c2ccccc2)CC1 | null | null | null |
609,432 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | [O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[NH:3]1.[CH3:20][O:21][C:22](=[O:46])[C@H:23]([CH2:44]O)[NH:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30]... | COC(=O)[C@H](CO)NC(c1ccccc1)(c1ccccc1)c1ccccc1 | CC(C)(C)OC(=O)N1CCC2(CC1)NC(=O)NC2=O | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 3.6 g (13.37 mmol) of (34.2) in 15 ml of absolute THF is added to a solution of 3.72 g (10.3 mmol) of (34.3) and 3.5 g (13.34 mmol) of triphenylphosphine in 20 ml of absolute THF. 2.11 ml (13.37 mmol) of diethyl azodicarboxylate (DEAD) are added to this solution and the reaction mixture is stirred at room... | COC(=O)[C@H](CN1C(=O)NC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O)NC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | 95.1 | null |
1,684,623 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [NH2:1][CH:2]([C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=1[O:19][CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=O.[F:21][C:22]1[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O>>[CH3:20][O:19][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:11]=1[CH:2... | O=Cc1cccc(-c2ccccn2)c1F | COC(=O)CCCCC(N)c1c(OC)cccc1OC | null | null | null | null | null | null | null | 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 according to the described general procedure 1 (GP1) by reaction of methyl 6-amino-6-(2,6-dimethoxyphenyl)hexanoate with 2-fluoro-3-(pyridin-2-yl)benzaldehyde. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.72 min.; [M+H]+: 435.13 g/mol. | COc1cccc(OC)c1C1CCCCC(=O)N1Cc1cccc(-c2ccccn2)c1F | null | null | null |
762,900 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:6]=[C:5]([S:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])[S:4][C:3]=1[N:16]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]1.[Cl:25][C:26]1[CH:36]=[C:35]([F:37])[C:34]([F:38])=[CH:33][C:27]=1[C:28]([N:30]=[C:31]=[O:32])=[O:29]>C(#N)C>[Cl:25][C:26]1[CH:36]=[C:35]([F... | O=C=NC(=O)c1cc(F)c(F)cc1Cl | Nc1cc(S(=O)(=O)N2CCCCC2)sc1N1CCC(C(=O)O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 3 | 1-[3-Amino-5-(piperidine-1-sulfonyl)thiophen-2-yl]piperidine-4-carboxylic acid (0.2 g of crude product) is dissolved in 2 ml of acetonitrile and admixed with the equimolar solution of 2-chloro-4,5-difluorobenzoyl isocyanate in acetonitrile, and the mixture is stirred at RT. After 3 hours, the solid is filtered off with... | O=C(NC(=O)c1cc(F)c(F)cc1Cl)Nc1cc(S(=O)(=O)N2CCCCC2)sc1N1CCC(C(=O)O)CC1 | null | null | null |
876,842 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | [CH2:1]([N:3]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])[C:4](=[O:24])[CH2:5][C:6]1[CH:23]=[CH:22][C:9]([CH2:10][O:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1)[CH3:2].[OH-].[K+]>CCO>[CH2:1]([N:3]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])[C:... | CCN(Cc1ccccc1F)C(=O)Cc1ccc(COc2ccccc2C(=O)OC)cc1 | null | null | [K+] | [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 | null | null | Methyl 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethyl}benzyl)oxy]benzoate (0.242 g, 0.555 mmol) was dissolved in EtOH (5 ml, 95%), potassium hydroxide (0.062 g, 1.111 mmol) was added. The reaction was performed in an single node microwave oven (7 min, 150° C.). Work-up by removing the solvent by evaporation and addit... | CCN(Cc1ccccc1F)C(=O)Cc1ccc(COc2ccccc2C(=O)O)cc1 | null | 5.6 | null |
1,431,927 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | Cl[C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]2[N:5]=[CH:4][C:3]=1[C:16]([N:18]1[CH2:23][CH2:22][C:21]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[O:25][CH2:24]2)[CH2:20][CH2:19]1)=[O:17].[CH3:32][C:33]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][C:34]=1[NH2:35]>>[CH3:32][C:33]1[CH:39]=[CH... | CCOC(=O)c1cnn2c(Cl)c(C(=O)N3CCC4(CC3)COc3ccccc34)cnc12 | Cc1ccc(C)c(N)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In the same manner as in Example 19, step 5 and using 7-chloro-3-ethoxycarbonyl-6-(2H-spiro[benzofuran-3,4′-piperidine]-1′-ylcarbonyl)pyrazolo[1,5-a]pyrimidine (0.24 g, 0.54 mmol) obtained in Example 128, step 2 and 2,5-dimethylaniline (0.098 g, 0.81 mmol), the title compound (0.25 g, 86%) was obtained. | CCOC(=O)c1cnn2c(Nc3cc(C)ccc3C)c(C(=O)N3CCC4(CC3)COc3ccccc34)cnc12 | null | 88.1 | null |
1,526,670 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]([C:4]1[N:5]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:6]=[C:7]([C:9]([NH:11][C@@H:12]([CH3:29])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([C:26]#[N:27])=[C:21]([Cl:28])[CH:20]=3)=[N:15]2)=[O:10])[N:8]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[Cl:28][C:21]1[CH:20]... | CC(=O)c1nc(C(=O)N[C@@H](C)Cn2ccc(-c3cc(F)c(C#N)c(Cl)c3)n2)cn1COCC[Si](C)(C)C | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 3 | (S)-2-Acetyl-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide (290 mg, 0.53 mmol) was dissolved in MeOH (20 ml). NaBH4 (30 mg, 0.79 mmol) was added to the solution in portions at 0° C. and the mixture was stirred at RT for 3 h. The r... | CC(O)c1nc(C(=O)N[C@@H](C)Cn2ccc(-c3cc(F)c(C#N)c(Cl)c3)n2)cn1COCC[Si](C)(C)C | null | null | null |
527,783 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | [H-].[Na+].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4]1.I[CH2:13][CH2:14][CH:15]1[CH2:21][CH2:20][C:19]2[C:22]([O:32][CH3:33])=[C:23]([O:30][CH3:31])[C:24]([O:28][CH3:29])=[C:25]([O:26][CH3:27])[C:18]=2[CH2:17][CH2:16]1>C1COCC1.O>[CH3:27][O:26][C:25]1[C:18]2[CH2:17][CH2:16][CH:15]([CH2:14][CH2:13][N:3]3... | COc1c2c(c(OC)c(OC)c1OC)CCC(CCI)CC2 | c1ccc2[nH]nnc2c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a suspension of sodium hydride (60% oil dispersion, 230 mg) in THF (6 ml) was added a solution of 1,2,3-benzotriazole (680 mg) in THF(6 ml) with cooling with ice. The reaction mixture was warmed to room temperature and stirred at ambient temperature for 30 min. 7-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro... | COc1c2c(c(OC)c(OC)c1OC)CCC(CCn1nnc3ccccc31)CC2 | null | 78.3 | null |
1,663,628 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([C:34](O)=[O:35])=[N:32][CH:33]=4)=[C:14]([C:16]#[C:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[CH3:37][S:38]([NH2:41])(=[O:40])=[O:39].C1(N=C=NC2CCCCC2)... | O=C(O)c1ccc(-c2c(C#Cc3ccc4ccccc4n3)nc3c(N4CCOCC4)ccnn23)cn1 | CS(N)(=O)=O | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccncc1 | 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 compound 40a (0.20 g, 0.42 mmol), methanesulfonamide (60 mg, 0.63 mmol), dicyclohexylcarbodiimide (90.0 mg, 0.44 mmol) and N,N-dimethylpyridin-4-amine (60.0 mg, 0.49 mmol) in DCM (5 mL) was stirred at rt overnight, then concentrated under reduced pressure. The residue obtained was purified by flash column... | CS(=O)(=O)NC(=O)c1ccc(-c2c(C#Cc3ccc4ccccc4n3)nc3c(N4CCOCC4)ccnn23)cn1 | null | null | null |
174,914 | ord_dataset-4937da99a6a247eb90fa70f0d2eac3db | null | 1988-01-01T00:07:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[O:14][CH3:15].Cl[C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C>O1CCCC1>[CH3:20][O:19][C:17]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[O:14][CH3:15])=[O:18] | COc1cc(OC)c2ccccc2c1O | COC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 1.27 g of 1-hydroxy-2,4-dimethoxynaphthalene, prepared as shown in Preparations 7 and 8, in 50 ml of tetrahydrofuran was added 0.694 g of methyl chloroformate followed by 0.743 g of triethylamine. The mixture was stirred at room temperature for 16 hours, filtered, then the solvent removed under reduced... | COC(=O)Oc1c(OC)cc(OC)c2ccccc12 | null | null | null |
170,576 | ord_dataset-41558b7e18dd41999311b1762e0e13a3 | null | 1988-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[F:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([CH:21]2[CH2:26][CH2:25][N:24]([C:8](=[O:9])[C:7]3[CH:11]... | O=C(c1ccc(F)cc1)C1CCNCC1 | O=C(Cl)c1ccc([N+](=O)[O-])cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 1 | 4-Nitrobenzoyl chloride (3.08 g) was added slowly to a stirred mixture of 4-(4-fluorobenzoyl)piperidine hydrochloride (4.0 g) and triethylamine (4.98 g) in methylene chloride (110 ml) at room temperature. The resulting mixture was stirred at this temperature for 1 hour, washed with 1N hydrochloric acid, saturated sodiu... | O=C(c1ccc(F)cc1)C1CCN(C(=O)c2ccc([N+](=O)[O-])cc2)CC1 | null | 85.5 | null |
42,681 | ord_dataset-4c8627b52d564809adb9b494879c07c0 | null | 1978-01-01T00:07:00 | true | C1(C)C=CC=CC=1.[C:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=1[CH2:17][CH:18]1[C:22](=[O:23])[C:21](=[O:24])[CH2:20][C:19]1=[O:25])([O:10][CH3:11])=[O:9]>CC(O)C.[Pd]>[C:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=1[CH2:17][CH:18]1[C:22](=[O:23])[CH:21]([OH:24])[CH2... | COC(=O)CCCc1ccccc1CC1C(=O)CC(=O)C1=O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CC(C)O | null | null | null | null | null | null | null | null | null | null | 72 | A toluene solution of 30.5 g (0.1 mol) of 2-[2-(3-carbomethoxypropyl)benzyl]-1,3,4-cyclopentanetrione, XIIa, was thoroughly dried by azeotropic distillation. Removal of the toluene gave a red oil that was taken up in 200 ml of 2-propanol. Five grams of Pd/C was added and the compound hydrogenated at 0.25 psi for 3 days... | COC(=O)CCCc1ccccc1CC1C(=O)CC(O)C1=O | null | null | null |
1,401,653 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:17]>COCCOC>[Br:17][CH2:14][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1 | BrP(Br)Br | Cc1noc(-c2ccc(Br)cc2)c1CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 25 | 1 | [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-methanol (2.88 g, 10.74 mmol) in DME (23 mL) was treated with phosphorus tribromide (1.5 mL, 16.11 mmol), and the reaction was stirred at room temperature for 1 hour. Aqueous workup provided the title compound. | Cc1noc(-c2ccc(Br)cc2)c1CBr | null | null | null |
275,681 | ord_dataset-02ee2261663048188cf6d85d2cc96e3f | null | 1993-01-01T00:09:00 | true | [C:1]([CH:4]([CH2:9][CH:10]=[C:11]([CH3:22])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:21])[CH2:16][O:17][CH2:18][O:19][CH3:20])C(OC)=O)(=[O:3])[CH3:2].[Cl-].[Na+].O>CS(C)=O>[CH3:22][C:11]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:21])[CH2:16][O:17][CH2:18][O:19][CH3:20])=[CH:10][CH2:9][CH2:4][C:1](=[O:3])[CH3:2] | COCOCC(C)=CCCC(C)=CCC(C(C)=O)C(=O)OC | null | null | [Cl-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 150 | 5 | To a solution of methyl 2-acetyl-5,9-dimethyl-10-(methoxymethyl)oxy-4,8-decadienate (420 mg, 1.37 mmol) in methylsulfoxide (4 ml) were added sodium chloride (160 mg, 2.74 mmol) and water (0.1 ml), and the mixture was stirred at 150° C. After five hours, the reaction mixture was allowed to cool to room temperature, and ... | COCOCC(C)=CCCC(C)=CCCC(C)=O | null | 102.7 | null |
1,521,877 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [OH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)[CH:15]=3)[CH:9]=2)[CH:4]=[CH:3]1.Br[C:30]1[N:35]=[CH:34][CH:33]=[CH:32][N:31]=1>>[NH:19]1[CH2:20][CH2:21][CH:16]([N:14]2[CH:15]=[C:11]([C:8]3[CH:9]=[C:10]4[N:2]([O:1][C:30]5[N:35]=[CH... | CC(C)(C)OC(=O)N1CCC(n2cc(-c3cnc4ccn(O)c4c3)cn2)CC1 | Brc1ncccn1 | null | null | null | null | null | null | null | 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 entitled compound is prepared from tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate and 2-bromo-pyrimidine as described in the last 2 steps of Example 18. | c1cnc(On2ccc3ncc(-c4cnn(C5CCNCC5)c4)cc32)nc1 | null | null | null |
1,033,900 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [H-].[Na+].[Br:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Br[CH2:10][C:11]1([CH3:15])[CH2:14][O:13][CH2:12]1>CN(C=O)C.C([O-])(O)=O.[Na+]>[Br:3][C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]2([CH3:15])[CH2:14][O:13][CH2:12]2)[CH:8]=1 | Brc1cn[nH]c1 | CC1(CBr)COC1 | null | O=C([O-])O | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 1.5 | To a suspension of NaH (98 mg, 55% in mineral oil, 2.25 mmol) in DMF (1.2 ml) was added a solution of 4-bromopyrazole (300 mg, 2.04 mmol) in DMF (2 ml). The reaction mixture was stirred at room temperature for 15 minutes before a solution of 3-bromomethyl-3-methyloxetane (404 mg, 2.45 mmol) in DMF (2 ml) was added slow... | CC1(Cn2cc(Br)cn2)COC1 | null | 94.2 | null |
699,412 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=2)=[O:10])=[CH:4][C:3]=1[NH:23][C:24](=[O:35])[C:25]1[CH:30]=[C:29](Cl)[CH:28]=[CH:27][C:26]=1[N+:32]([O-:34])=[O:33].[CH3:36][NH:37][CH2:38][CH2:39][CH2:40][NH:41][CH3:42]>>[CH3:1][C:2... | CNCCCNC | Cc1ccc(NC(=O)c2ccnc(N3CCOCC3)c2)cc1NC(=O)c1cc(Cl)ccc1[N+](=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 | In an analogous procedure to that described in the fifth paragraph of the portion of Note a) which is concerned with the preparation of starting materials, N-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]-5-chloro-2-nitrobenzamide was reacted with N-(3-methylaminopropyl)-N-methylamine to give N-[2-methyl-5-(2... | CNCCCN(C)c1ccc([N+](=O)[O-])c(C(=O)Nc2cc(NC(=O)c3ccnc(N4CCOCC4)c3)ccc2C)c1 | null | null | null |
1,660,684 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[C:6]#[N:7].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CC(N(C)C)=O>[CH3:13][O:12][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[O:11][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][... | COc1cc(C#N)cc(OC)c1O | ClCCN1CCOCC1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 100 | 6 | 6.06 g 3,5 Dimethoxy-4-hydroxy-benzonitrile was dissolved in 20 mL dimethylacetamide, 5.2 g potassium carbonate and 6.7 g N-(2-chloroethyl)morpholine hydrochloride was added and the mixture was stirred at 100° C. for 6 h. The solvent was distilled off and the residue was co-evaporated twice with toluene. The residue wa... | COc1cc(C#N)cc(OC)c1OCCN1CCOCC1 | null | null | null |
560,117 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | C([N:4]1[C:13]2[C:8](=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([NH2:17])[CH2:5]1)(=O)C.[OH-].[K+].O>CCO>[NH2:17][C:6]1[CH:5]=[N:4][C:13]2[C:8]([CH:7]=1)=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=[CH:11][CH:12]=2 | CC(=O)N1CC(N)=Cc2c1cccc2[N+](=O)[O-] | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | N-Acetyl-3-amino-5-nitroquinoline, as described above in Step B, (5.89 g, 25.5 mmol) was dissolved in EtOH (200 mL) and KOH (2 N aqueous solution, 19.2 mL, 38.4 mmol) was added. The reaction mixture was heated to reflux for 48 hours, cooled, poured into water, and concentrated to in vacuo to remove the EtOH. The result... | Nc1cnc2cccc([N+](=O)[O-])c2c1 | null | null | null |
1,008,540 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | ClCC([NH:5][CH2:6][C:7]1[C:8]([OH:28])=[C:9]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:10]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][C:12]=1[C:13]([CH3:16])([CH3:15])[CH3:14])=O.Cl>C(O)C>[NH2:5][CH2:6][C:7]1[C:12]([C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:11][C:10]([C:17]([CH3:18])([CH3:19])[CH3:20])=[C... | CC(C)(C)c1cc(C(C)(C)C)c(-c2ccc(Cl)cc2)c(O)c1CNC(=O)CCl | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 75 | null | To a mixture of 0.30 g (0.71 mmol) of the product from Step C in 20 mL ethanol was added 3 mL conc. hydrochloric acid and the resulting solution was stirred and heated overnight at 75° C. The reaction mixture was then cooled to room temperature, concentrated in vacuo and the residue was partitioned between EtOAc and sa... | CC(C)(C)c1cc(C(C)(C)C)c(-c2ccc(Cl)cc2)c(O)c1CN | null | null | null |
1,488,322 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [Si:1]([O:8][CH2:9][C@@H:10]([NH2:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:13][C:14]1[C:19]([CH2:20][CH:21]=O)=[C:18](Cl)[N:17]=[CH:16][N:15]=1>C(O)C>[Si:1]([O:8][CH2:9][C@@H:10]([N:12]1[C:18]2[N:17]=[CH:16][N:15]=[C:14]([Cl:13])[C:19]=2[CH:20]=[CH:21]1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])... | O=CCc1c(Cl)ncnc1Cl | C[C@H](N)CO[Si](C)(C)C(C)(C)C | 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 | (S)-2-tert-Butyldimethylsilyloxy-1-methylethylamine (120 g, 636 mmol) was added to (4,6-dichloropyrimidin-5-yl)acetaldehyde (52.8 g, 276 mmol) in ethanol (500 mL). The mixture was heated to reflux for 45 minutes. The reaction mixture was evaporated in vacuo then the residue was diluted with water (400 mL) and extracted... | C[C@@H](CO[Si](C)(C)C(C)(C)C)n1ccc2c(Cl)ncnc21 | null | 67 | null |
1,680,479 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]#N)=[CH:10][C:4]=2[O:3]1.[OH2:13]>C(O)=O.[Al].[Ni]>[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:13])=[CH:10][C:4]=2[O:3]1 | O | N#Cc1ccc2[nH]c(=O)oc2c1 | null | [Ni] | [Al] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile (Intermediate 6, 220 mg; 1.37 mmol) and aluminium/nickel 1:1 alloy (223.6 mg; 2.61 mmol) in 2.25 ml of formic acid and 0.75 ml of water is stirred at 90° C. for 24 hr. The solid is filtered and washed with ethanol. The filtrate is concentrated in vacuo and d... | O=Cc1ccc2[nH]c(=O)oc2c1 | null | 97 | null |
478,886 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | C(C(NC(C1C=C(F)C=CC=1S[S:20][N:21]([C:30](=[O:38])[C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][CH:32]=1)[CH:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([OH:25])=[O:24])=O)CC(C)C)(O)=O.BrBr>C(#N)C.ClCCl>[CH3:28][CH:27]([CH3:29])[CH2:26][C@H:22]([N:21]1[C:30](=[O:38])[C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[... | CC(C)CC(NC(=O)c1cc(F)ccc1SSN(C(=O)c1cccc(F)c1)C(CC(C)C)C(=O)O)C(=O)O | null | null | BrBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | ClCCl | null | null | null | null | null | null | null | null | null | null | null | Following the general method of Example 3, a slurry of {s-(R*,R*)]-2-{-[2-(1-carboxy-3-methyl-butylcarbamoyl)-4-fluorophenyldisulfanyl]-5-fluorobenzoylamino}-4-methyl-pentanoic acid (2.1 g, 3.6 mmol) (from Preparation 21) in 8 mL acetonitrile and 25 mL dichloromethane was treated with bromine (0.7 g, 4.4 mmol) in 15 mL... | CC(C)C[C@@H](C(=O)O)n1sc2ccc(F)cc2c1=O | null | 137.3 | null |
788,383 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:10][C:11]([CH3:13])=O>CO>[C:11](=[N:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)([CH3:13])[CH3:10] | COc1ccc(N)cn1 | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 5-amino-2-methoxypyridine (18 g, 161 mmol) in methanol (80 mL) was added acetone (20 mL, 177 mmol). The reaction was heated at reflux for 24 hours and the volatiles were concentrated in vacuo to provide 21.3 g of isopropylidene-(6-methoxy-pyridin-3-yl)-amine. 1H NMR (CDCl3) δ 7.59 (d, 1H), 7.31 (m, 1H)... | COc1ccc(N=C(C)C)cn1 | null | 80.6 | null |
352,618 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:37])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=2)[N:9]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])(=[O:19])=[O:18])[C:8]1=[O:30].O>N1C=CC=CC=1>[Cl:16][C:13]1[CH:14]=[C:15]2[C:1... | COc1ccc(S(=O)(=O)N2C(=O)C(N)(c3ccccc3Cl)c3cc(Cl)ccc32)c(OC)c1 | CCC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 25 | 1 | 0.08 g of propionyl chloride is added to a solution of 0.33 g of the compound obtained in EXAMPLE 3 in 3 ml of pyridine and the reaction mixture is stirred for 1 hour at RT. It is poured into water, extracted with AcOEt, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica usi... | CCC(=O)NC1(c2ccccc2Cl)C(=O)N(S(=O)(=O)c2ccc(OC)cc2OC)c2ccc(Cl)cc21 | null | null | null |
1,006,405 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[C:14]([CH2:16]O)[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18... | O=C1NC(=O)c2ccccc21 | OCc1cc2ccc(OCc3ccccc3)cc2o1 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a tetrahydrofuran (300 mL) solution of (6-benzyloxy-benzofuran-2-yl)-methanol (14.2 g, 55.8 mmol) described in Production Example 1-2-2 were added phthalimide (9.03 g, 61.4 mmol), triphenylphosphine (17.6 g, 67 mmol) and diethylazodicarboxylate (29.2 g, 67 mmol) at 0° C., which was stirred at room temperature for 7 ... | O=C1c2ccccc2C(=O)N1Cc1cc2ccc(OCc3ccccc3)cc2o1 | null | null | null |
784,122 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:15][CH2:16][CH3:17].[CH:18](O)=O>CCOC(C)=O>[CH2:16]([N:15]1[C:3]2[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=2[N:1]=[CH:18]1)[CH3:17] | CCNc1cc(C(=O)OC)cc([N+](=O)[O-])c1N | O=CO | 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 | 100 | 0.75 | Methyl 4-amino-3-(ethylamino)-5-nitrobenzoate (D205) (850 mg, 3.55 mmol, 1 equiv) was dissolved in formic acid (20 ml) and the resulting solution was stirred at 100° C. for 45 min then cooled to room temperature and diluted with AcOEt (200 ml). The organic phase was washed with a 2N aqueous NaOH solution, dried over Mg... | CCn1cnc2c([N+](=O)[O-])cc(C(=O)OC)cc21 | null | 79 | null |
1,172,490 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH:8]([CH3:12])[C:9](Cl)=[O:10])[N:3]=1.[O:13]=[C:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH:8]([CH3:12])[C:9]([CH:19]2[C:14](=[O:13])[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]... | Cc1cc(C)n(C(C)C(=O)Cl)n1 | CC(C)(C)OC(=O)N1CCC(=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 | tert-Butyl 3-(2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoyl)-4-oxopiperidine-1-carboxylate (0.248 g, 23.87% yield) was synthesised from 2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoyl chloride (0.5 g, 2.97 mmol, example 104b) and tert-butyl 4-oxopiperidine-1-carboxylate (1.185 g, 5.95 mmo) by the general procedure for the prepar... | Cc1cc(C)n(C(C)C(=O)C2CN(C(=O)OC(C)(C)C)CCC2=O)n1 | null | 23.9 | null |
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