original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,766,667 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH:4]=O.[CH3:11][S:12]([CH2:14][S:15][CH3:16])=[O:13].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[CH3:11][S:12]([C:14]([S:15][CH3:16])=[CH:4][C:3]1[C:2]([CH3:1])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:10])=[O:13] | Cc1cccc(C)c1C=O | CSCS(C)=O | null | C[N+](C)(C)Cc1ccccc1 | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 80 | 16 | To a solution of 2,6-dimethyl-benzaldehyde (14.6 g, 109 mmol) in 1,4-dioxane (24.7 mL) was added methyl methylsulfinylmethyl sulfide (13.5 g, 109 mmol) followed by benzyltrimethylammonium hydroxide (9.10 g, 54.4 mmol). The resulting mixture was heated at 80° C. After 16 h, the mixture was cooled to rt and concentrated.... | CSC(=Cc1c(C)cccc1C)S(C)=O | null | 68.3 | null |
427,532 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=2)[O:3]1.[Br:18]Br>C(O)(=O)C>[Br:18][C:5]1[CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[C:9]2[C:4]=1[O:3][C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10]2 | CCOC(=O)c1ccc2c(c1)CCC(C)(C)O2 | BrBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | Reaction Scheme 6B discloses a synthetic route to specific preferred benzopyran (chromene) compounds of the invention where with reference to Formula 1 the Z group is also CONH (amide derivatives). In accordance with this scheme, dihydrocoumarine (Compound 213) is subjected to a Grignard reaction with methyl magnesium ... | CCOC(=O)c1cc(Br)c2c(c1)CCC(C)(C)O2 | null | null | null |
135,071 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20]>O1CCCC1>[CH3:16][O:17][CH:18]([CH3:22])[C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:20] | COC(C)C(=O)Cl | CC1CC(=O)NN=C1c1ccc(N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 5.0 g (24.6 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 3.6 g (29.4 millimoles) of 2-methoxypropionyl chloride in 150 ml of absolute tetrahydrofuran were refluxed for 2 hours, while stirring. The mixture was evaporated down, the residue was stirred with water and the product was filtere... | COC(C)C(=O)Nc1ccc(C2=NNC(=O)CC2C)cc1 | null | 56.2 | null |
930,160 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH2:24][CH3:25])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1>>[CH2:24]([C:10]1[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([C:30]3[CH:31]=[CH... | CC1(C)OB(c2ccc(N)nc2)OC1(C)C | CCc1cc(-c2ccc(C(F)(F)F)cc2)cc(-c2cccc(Br)c2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-(3-bromo-phenyl)-6-ethyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.89) (0.30 g, 0.739 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.179 g, 0.813 mmol) according to the general procedure VI. Obtained as a white solid (0.0... | CCc1cc(-c2ccc(C(F)(F)F)cc2)cc(-c2cccc(-c3ccc(N)nc3)c2)n1 | null | null | null |
138,880 | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | null | 1985-01-01T00:12:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N+:3]=1[O-].[C:11]([O:14]C(=O)C)(=[O:13])[CH3:12]>>[C:11]([O:14][CH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1)(=[O:13])[CH3:12] | COc1cc[n+]([O-])c(C)c1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | To 2-methyl-4-methoxypyridine-N-oxide (23 g, 0.165 mole) in a 1 liter wide necked flask fitted with a large condenser was added ice-cool acetic anhydride (35 ml, 0.37 mole) with stirring. The mixture was allowed to warm to room temperature whereupon a vigorous exothermic reaction occurred. The dark mixture was stirred ... | COc1ccnc(COC(C)=O)c1 | null | 77.8 | null |
1,728,770 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH2:1]([N:5]([CH2:33][CH2:34][CH2:35][CH3:36])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[NH:11][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].[CH:43]1[CH:48]=[CH:47][C... | CCCCN(CCCC)C(=O)c1c[nH]c(-c2ccc(C(=O)OC)cc2C(=O)OCc2ccccc2)n1 | BrCCc1ccccc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC(C)(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 48 | To a stirred solution of 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate (200 mg, 0.4 mmol) in dry DMF (5 mL) was added K2CO3 (168 mg, 1.22 mmol) and 2-phenethyl bromide (90 mg, 0.48 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred for 48 h. The reaction mixture was... | CCCCN(CCCC)C(=O)c1cn(CCc2ccccc2)c(-c2ccc(C(=O)OC)cc2C(=O)OCc2ccccc2)n1 | null | 73.4 | null |
154,211 | ord_dataset-128a4f3f44e844218b1c319ab4de3893 | null | 1987-01-01T00:02:00 | true | C([O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=O)(=O)C.[C:17]([NH:19][C:20]([NH2:22])=[NH:21])#[N:18].[ClH:23]>O1CCOCC1>[ClH:23].[NH:19]([C:17]1[O:4][CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[N:18]=1)[C:20]([NH2:22])=[NH:21] | CC(=O)OCC(=O)c1ccc([N+](=O)[O-])cc1 | N#CNC(=N)N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 72 | A solution of 90 gm of 4-nitro-phenacyl acetate and 33.9 gm of 1-cyano-guanidine in 200 ml of dioxane and 20 ml of 5N hydrochloric acid was stirred for 2 days at room temperature. A first crop of the product was filtered off; the solution, after the addition of another 40 ml of 5N hydrochloric acid, was stirred for 3 d... | N=C(N)Nc1nc(-c2ccc([N+](=O)[O-])cc2)co1 | null | null | null |
226,604 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | C([Si](CC)(CC)[O:4][C:5]1([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:9][C:8](=[O:11])[CH:7]=[CH:6]1)C.Cl.C(O)C>O>[OH:4][C:5]1([C:12]([F:13])([F:14])[F:15])[CH:6]=[CH:7][C:8](=[O:11])[CH:9]=[CH:10]1 | CC[Si](CC)(CC)OC1(C(F)(F)F)C=CC(=O)C=C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 200 mg (0.68 mmol) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one and 1 mL of a solution of 1 part 37% hydrochloric acid in 9 parts absolute ethanol was heated at reflux overnight and poured into 10 mL of water. The resulting aqueous mixture was extracted with three 10 mL portions of dichlor... | O=C1C=CC(O)(C(F)(F)F)C=C1 | null | 90 | null |
1,538,540 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | C([O:3][C:4](=[O:19])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Li+]>C1COCC1.O>[C:16]([NH:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:19])=[O:3])(=[O:18])[CH3:17] | CCOC(=O)C(C)(C)Oc1cccc(NC(C)=O)c1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 24 | 2-(3-Acetylamino-phenoxy)-2-methyl-propionic acid ethyl ester (0.6 g, 2.2 mmol) was dissolved in THF (20 ml) and a solution of lithium hydroxide (0.33 g, 7.9 mmol) in water (5.8 ml) was added. The reaction mixture was allowed to stir at RT for 24 h. The solvent was removed under reduced pressure and the aqueous layer w... | CC(=O)Nc1cccc(OC(C)(C)C(=O)O)c1 | null | 86.2 | null |
1,702,431 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])(=[O:4])=[O:3].[CH:20]1([NH2:23])[CH2:22][CH2:21]1>N1C=CC=CC=1>[CH:20]1([NH:23][S:2]([C:5]2[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=2)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:... | NC1CC1 | C[Si](C)(C)CCOC(=O)c1cccc(S(=O)(=O)Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 2.00 g of 2-(trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate, 1.2 mL of cyclopropylamine, and 20 mL of pyridine was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and to the residue was added an aqueous citric acid solution, followed by extraction with ... | C[Si](C)(C)CCOC(=O)c1cccc(S(=O)(=O)NC2CC2)c1 | null | null | null |
1,618,457 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:12][C:13]1([F:32])[CH2:18][CH2:17][CH:16]([CH:19]([C:22]2[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[N:26][CH:27]=2)[CH2:20][NH2:21])[CH2:15][CH2:14]1>>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:21][CH2:20][CH:19]([CH:... | O=C(O)c1cccc(Cl)c1Cl | NCC(c1cnc(C(F)(F)F)nc1)C1CCC(F)(F)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The racemic mixture which was prepared in a similar manner to example 3a from 2,3-dichlorobenzoic acid and 2-(4,4-difluorocyclohexyl)-2-(2-(trifluoromethyl)pyrimidin-5-yl)ethanamine was separated into the two enantiomers by preparative SFC to yield the title compound. LCMS (MH+): m/z=482.1, tR (minutes, Method G)=2.76.... | O=C(NCC(c1cnc(C(F)(F)F)nc1)C1CCC(F)(F)CC1)c1cccc(Cl)c1Cl | null | null | null |
1,174,631 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [C:1]1([CH2:11][CH:12]2[N:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]3=[N:14][C:13]2=[S:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.ClCCl>[CH3:29][O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][S:21][CH:13]1[CH:... | COC(=O)CCCBr | S=C1N=C2C=CC=CN2C1Cc1cccc2ccccc12 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 18 | A mixture of 75 mg (0.26 mmol) of 3-naphthalen-1-ylmethyl-imidazo[1,2-a]pyridine-2-thione and 70 mg (0.39 mmol) of methyl 4-bromobutyrate and 72 mg (0.52 mmol) of potassium carbonate in 3 mL of 50% acetone in dichloromethane is stirred at room temperature for 18 h. The mixture is concentrated in vacuo and the residue i... | COC(=O)CCCSC1N=C2C=CC=CN2C1Cc1cccc2ccccc12 | null | null | null |
767,677 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[NH:21][C:20](=[O:22])[O:19][N:18]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>O1CCOCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[NH:21][C:20](=[O:22])[O:19][N:18]=4)[CH:15]=3... | O=c1[nH]c(-c2ccc3c(c2)c(-c2ccc(F)cc2)nn3C2CCCCO2)no1 | 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 | null | null | To a solution of 3-[3-(4-fluorophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazol-5-yl]-1,2,4-oxadiazolin-5-one (88 mg, 0.23 mmol) in dioxane (4.0 mL) was added 6 N HCl (4.0 mL) at ambient temperature. After stirring for 16 h an additional amount of dioxane (1.0 mL) was added and the reaction mixture was gently heated in a 60... | O=c1[nH]c(-c2ccc3[nH]nc(-c4ccc(F)cc4)c3c2)no1 | null | 19.1 | null |
1,587,346 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [Cl:1][C:2]1[C:3]([C:8](=[N:27][OH:28])[C:9]2[C:10](F)=[C:11]([F:25])[C:12]([N:17]3[CH2:22][C@H:21]([CH3:23])[O:20][C@H:19]([CH3:24])[CH2:18]3)=[C:13]([CH2:15][OH:16])[CH:14]=2)=[N:4][CH:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O>[Cl:1][C:2]1[C:3]([C:8]2[C:9]3[CH:14]=[C:13]([CH2:15][OH:16])[C:12]([N:17]4... | C[C@@H]1CN(c2c(CO)cc(C(=NO)c3nccnc3Cl)c(F)c2F)C[C@H](C)O1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | {5-[(3-chloropyrazin-2-yl)(hydroxyimino)methyl]-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3,4-difluorophenyl}methanol (Intermediate 198, 106 mg, 0.26 mmol) in MeCN (4 mL) was treated with K2CO3 (53.2 mg, 0.39 mmol) at 120° C. for 1 hr. The mixture was diluted with EtOAc and washed with water and brine. The EtOAc solution ... | C[C@@H]1CN(c2c(CO)cc3c(-c4nccnc4Cl)noc3c2F)C[C@H](C)O1 | null | 88.1 | null |
1,079,532 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [F:1][C:2]1([F:9])[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.CCN(CC)CC.[Cl:17][CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[Cl:17][CH2:18][CH2:19][CH2:20][C:21]([NH:8][CH:5]1[CH2:6][CH2:7][C:2]([F:9])([F:1])[CH2:3][CH2:4]1)=[O:22] | O=C(Cl)CCCCl | NC1CCC(F)(F)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | 4 | To a solution of 4,4-difluoro-cyclohexylamine (295 mg) and Et3N (0.91 mL) in 22 mL of CH2Cl2, add 4-chloro-butyryl chloride (0.42 g). Allow the resulting mixture to stand at room temp for 4 hr. Remove the organic solvent under vacuum. Dissolve the residue in Et2O. Wash the organic layer with 1N HCl, then brine, and the... | O=C(CCCCl)NC1CCC(F)(F)CC1 | null | 78.4 | null |
800,370 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | [C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[NH2:21][CH:22]1[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]1>>[N:24]12[CH2:29][CH2:28][CH:27]([CH2:26][CH2:25]1)[CH:22]([NH:21][C:16]([C:15]1[C:9]3[O:8][C:7]([C:1]4[CH:2]=[CH:3... | NC1CN2CCC1CC2 | O=C(O)c1cccc2nc(-c3ccccc3)oc12 | 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 | N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-phenylbenzoxazole-7-carboxamide was prepared from 2-phenylbenzoxazole-7-carboxylic acid and 3-aminoquinuclidine dihydrochloride using the method outlined in Step C of Example 7. This compound was obtained in 57% yield as a white solid: mp 179-180° C.; 1H NMR (300 MHz, CDCl3) δ 8.21 (dd... | O=C(NC1CN2CCC1CC2)c1cccc2nc(-c3ccccc3)oc12 | null | 57 | null |
1,207,835 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[C:17]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:18]([O:34][CH3:35])=[C:19]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[C:25]([F:32])[CH:24]=3)[CH:20]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>[Fe].CO.O>[NH2:29][... | COc1c(NC(=O)c2ccc([N+](=O)[O-])c(F)c2)cc(-c2cccnc2OCc2ccccc2)cc1C(C)(C)C | null | null | [Fe] | [Cl-] | [NH4+] | 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 | 105 | 8 | step 2—To a suspension of 316 (595 mg, 1.12 mmol) in a 1:1 mixture of MeOH/H2O (4 mL each) at RT was added NH4Cl (601 mg, 11.2 mmol) and iron powder (314 mg, 5.62 mmol). The reaction mixture was warmed to 105° C. and stirred overnight. The reaction was cooled to RT and filtered via Büchner funnel and the filtrate was r... | COc1c(NC(=O)c2ccc(N)c(F)c2)cc(-c2cccnc2OCc2ccccc2)cc1C(C)(C)C | null | 72.4 | null |
1,521,357 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14](C(O)=O)[NH:15]2)=[CH:11][C:10]=1[F:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN1CCCC1=O.[Cu]>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[F:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | O=C(O)c1cc2cc(F)c(OCc3ccccc3)cc2[nH]1 | null | null | [Cu] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of compound 4-2 (2.58 g, 9.07 mmol) and copper (2.97 g, 45.1 mmol) in 80 mL of 1-methylpyrrolidin-2-one was heated at reflux overnight under nitrogen. After cooling to room temperature, the mixture was filtered through Celite and washed with EtOAc. The filtrate was partitioned between water and EtOAc (2×150 m... | Fc1cc2cc[nH]c2cc1OCc1ccccc1 | null | 59.9 | null |
1,107,953 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:10]([CH2:18][CH3:19])=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=1.[Li+].[OH-].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[C:10]... | CCOC(=O)c1nc(-c2ccccc2Cl)n(-c2ccc(Cl)cc2)c1CC | null | null | Cl | [Li+] | [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 | 70 | 8 | Part A: Ethyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazole-4-carboxylate was obtained according to WO03040107. To a magnetically stirred solution of ethyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazole-4-carboxylate (5.80 g, 0.0149 mol) in tetrahydrofuran (40 ml) was added a solution of LiOH (... | CCc1c(C(=O)O)nc(-c2ccccc2Cl)n1-c1ccc(Cl)cc1 | null | 84 | null |
938,638 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2[O:15][C:16](Br)=[CH:17][CH:18]=2)=[O:13])[CH:6]=1.[CH:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)([CH3:23])[CH3:22]>>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2[O:15][C:16]([... | CC(C)c1cccc(B(O)O)c1 | COC(=O)Cc1cccc(NC(=O)c2ccc(Br)o2)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 | Methyl ester (16) (100 mg, 0.30 mmol) was coupled to 3-isopropyl-phenylboronic acid (53 mg, 0.33 mmol) using Method E. The crude compound was purified by column chromatography, eluting in 17% EtOAc in heptane to give the title compound. | COC(=O)Cc1cccc(NC(=O)c2ccc(-c3cccc(C(C)C)c3)o2)c1 | null | null | null |
134,429 | ord_dataset-b76b52f4448a4eedb28ffcd8f902046a | null | 1985-01-01T00:09:00 | true | [CH:1]([C:3]1[CH:16]=[CH:15][C:6]([CH:7]=[C:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].[BH4-]>C(O)C>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[C:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:15][CH:16]=1 | CCOC(=O)C(C)=Cc1ccc(C=O)cc1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a suspension of 10.0 g of 50% sodium hydride (dispersion in mineral oil) in freshly distilled dimethoxyethane (DME, 350 ml) stirred under nitrogen at 10° is added 53.6 ml of triethyl 2-phosphonopropionate in ca. 40 minutes. The mixture is stirred for 0.5 hour at 10° and for an additional 1.5 hours during which time ... | CCOC(=O)C(C)=Cc1ccc(CO)cc1 | null | null | null |
180,972 | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | null | 1988-01-01T00:11:00 | true | [NH2:1][CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:8][CH3:9])[O:6][CH3:7].[CH:12](OC)=[O:13]>>[CH3:9][O:8][Si:5]([O:10][CH3:11])([O:6][CH3:7])[CH2:4][CH2:3][CH2:2][NH:1][CH:12]=[O:13] | CO[Si](CCCN)(OC)OC | COC=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 | 3 | A mixture of 7 parts (39 mmol.) of 3-aminopropyltrimethoxysilane and 20 parts (330 mmol.) of methyl formate was heated under reflux in a nitrogen atmosphere. The reaction was monitored by gas chromatography and was found to be complete after 3 hours. Volatiles were then removed in vacuum, yielding the desired N-(3-trim... | CO[Si](CCCNC=O)(OC)OC | null | null | null |
1,198,485 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][CH2:26][OH:27])[CH:13]=[N:12]2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][C:29]1([CH3:41])[O:33][C@H:32]([CH2:34][N:35]2[CH:39]=[CH:38][C:37]([NH2:40])=[N:36]2)[CH2:31][O:30]1>>[CH:1]1([CH2:... | CC1(C)OC[C@@H](Cn2ccc(N)n2)O1 | O=C(O)C(CC1CCCC1)n1ncc(Oc2ccccc2CCO)cc1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the method described in Example 49, 3-cyclopentyl-2-{4-[2-(2-hydroxy-ethyl)-phenoxy]-6-oxo-6H-pyridazin-1-yl}-propionic acid (Intermediate 79) and 1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-ylamine (Intermediate 4) afforded impure 3-cyclopentyl-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-p... | CC1(C)OC[C@@H](Cn2ccc(NC(=O)C(CC3CCCC3)n3ncc(Oc4ccccc4CCO)cc3=O)n2)O1 | null | null | null |
1,056,832 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | B(Br)(Br)[Br:2].[C:5]1([CH:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClCCl>[Br:2][CH:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:12][CH2:13][CH2:14][CH2:15][OH:16] | BrB(Br)Br | OCCCCC(O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 1 | Boron tribromide (1.2 mL, 12.69 mol) was slowly added to a dichloromethane solution (40 mL) of 1-phenylpentane-1,5-diol (1.89 g, 10.52 mmol) at 0° C. The reaction mixture was stirred for one hour and quenched with water. The aqueous layer was extracted with dichloromethane (3×10 mL), and the combined organics were drie... | OCCCCC(Br)c1ccccc1 | null | null | null |
95,282 | ord_dataset-6f715747ea754945a2f0af4a8482c7d2 | null | 1982-01-01T00:06:00 | true | Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][CH2:14][OH:15])[CH:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+].[H][H]>[Pd].CO>[OH:15][CH2:14][CH2:13][N:6]1[CH:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]2[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=2)[NH:8][C:7]... | O=C1Nc2ccc(Cl)cc2C(c2ccccc2)N1CCO | [H][H] | null | [Pd] | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 14 parts of 6-chloro-3,4-dihydro-3-(2-hydroxyethyl)-4-phenyl-2(1H)-quinazolinone, 5 parts of sodium acetate and 200 parts of methanol is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catal... | O=C1Nc2ccccc2C(c2ccccc2)N1CCO | null | 91 | null |
285,017 | ord_dataset-d63ab258f4634f87bdebbaff0a341c28 | null | 1994-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[Cl:16][CH2:17][C:18]([NH:20][C:21]1[CH:31]=[CH:30][C:24]([CH:25]=[CH:26][C:27](Cl)=[O:28])=[CH:23][CH:22]=1)=[O:19]>>[Cl:16][CH2:17][C:18]([NH:20][C:21]1[CH:31]=[CH:30][C:24]([CH:25]=[CH:26][C:27]([N:13]2[CH2:1... | Clc1ccc(CCN2CCNCC2)cc1 | O=C(Cl)C=Cc1ccc(NC(=O)CCl)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 | Analogously to Example 7, 1-[2-(4-chlorophenyl)ethyl]piperazine and 4-chloroacetylaminocinnamic acid chloride are reacted to form 1-{3-[4-(N-chloroacetylamino)phenyl]prop-2-en-1-on-yl}-4-[2-(4-chlorophenyl)ethyl]piperazine. | O=C(CCl)Nc1ccc(C=CC(=O)N2CCN(CCc3ccc(Cl)cc3)CC2)cc1 | null | null | null |
1,274,978 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][C:2]1([CH3:16])[CH:6]([CH3:7])[CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12].C1COCC1>[OH-].[Na+]>[CH3:16][C:2]1([CH3:1])[CH:6]([CH3:7])[CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12] | CCOC(=O)CCCC1CCC(C)C1(C)C | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 110 | null | Ethyl 4-(2,2,3-trimethylcyclopentyl)butanoate (5 g, 22 mmol) was added to THF (25 ml) into a round bottom flask. Aqueous 1 N NaOH (25 ml) was then added to the flask and the reaction mixture was refluxed at 110° C. for 8 h. Upon completion of the reaction, the reaction mixture was diluted with 1 N NaOH (25 ml) and the ... | CC1CCC(CCCC(=O)O)C1(C)C | null | 87.6 | null |
298,498 | ord_dataset-b6309a86b70f4ca08fd301828cacf950 | null | 1994-01-01T00:10:00 | true | [CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:9](=[O:48])[N:8]2[N:49]=[C:50]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH:51]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]... | CCCCc1nc2cc(-c3ccccc3)nn2c(=O)n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 800 mg of the product of Example 7 in 100 ml of acetone containing 3 drops of 5% HC1 is refluxed for 16 hours. The reaction mixture is concentrated in vacuo to a residue which is purified by column chromatography on silica gel by elution with 70% ethyl acetate-hexanes to give 350 mg of the desired product... | CCCCc1nc2cc(-c3ccccc3)nn2c(=O)n1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1 | null | 64.8 | null |
914,594 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [F:1][C:2]1([F:35])[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][C:19]=4[CH3:33])[N:14]=3)=[CH:9][C:8]=2I)[CH2:3]1.[CH3:36][Si:37]([C:40]#[CH:41])([CH3:39])[CH3:38].C(NC(C)C)(C)C>O1C... | Cc1cc(CCC(=O)OC(C)(C)C)ccc1-c1noc(-c2cnc(N3CCC(F)(F)C3)c(I)c2)n1 | C#C[Si](C)(C)C | null | CC(C)(C)[P]([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C | I[Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)NC(C)C | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 61 mg (0.10 mmol) of tert-butyl 3-(4-(5-(6-(3,3-difluoropyrrolidin-1-yl)-5-iodopyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate (from EXAMPLE 34) in 5.0 mL of 1,4-dioxane were added 1 mg (0.005 mmol) of copper(II) iodide, 20 mg (0.21 mmol) of (trimethylsilyl)acetylene, 12 mg (0.12 mmol) of... | Cc1cc(CCC(=O)OC(C)(C)C)ccc1-c1noc(-c2cnc(N3CCC(F)(F)C3)c(C#C[Si](C)(C)C)c2)n1 | null | 75.9 | null |
1,628,424 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9][C@@H:10]([OH:14])[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:36][C:37]1[O:38][C:39](=[O:43])[O:40][C:41]=1[CH3:42].CCOC(C)=O>CN(C=... | Cc1oc(=O)oc1CCl | CC(C)(C)OC(=O)N[C@H](Cc1ccc(-c2ccccc2)cc1)C[C@@H](O)C(=O)O | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 0.5 | (2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic acid (500 mg, 1.0 mmol, 1.0 eq.) was dissolved in dry DMF (10.0 mL). The solution was cooled to 0° C. and dicesium carbonate (465 mg, 1.4 mmol, 1.1 eq.) was added. The mixture was stirred for 30 minutes and 4-chloromethyl-5-methyl-1,3-dioxol-2-one (212 ... | Cc1oc(=O)oc1COC(=O)[C@H](O)C[C@@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)OC(C)(C)C | null | null | null |
1,663,128 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [C:1]1([C:7]2[N:8]([CH2:16][C:17]3[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:27][OH:28].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>N1C=CC=CC=1>[OH:28][NH:27][C:21](=[O:22])[C:... | NO | O=C(O)c1ccc(Cn2c(-c3ccccc3)cc3ccccc32)cc1 | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | Cl | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | Title compound 496 (332 mg, 1.014 mmol), hydroxylamine hydrochloride (85 mg, 1.217 mmol), BOP (583 mg, 1.318 mmol), triethylamine (0.424 mL, 3.04 mmol) and pyridine (7 mL) were stirred together at room temperature for 1 hour. All solvents were then removed under reduced pressure, and the residue was diluted with ethyl ... | O=C(NO)c1ccc(Cn2c(-c3ccccc3)cc3ccccc32)cc1 | null | 16.7 | null |
1,309,586 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | Br[C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][CH:21]([N:24]5[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]5)[CH2:20][CH2:19]4)=[CH:14][C:13]=3[O:31][CH3:32])=[N:9]2)=[CH:4][CH:3]=1.[C:33]([NH:37][S:38]([C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=1)(=[O:40])=... | COc1cc(N2CCC(N3CCN(C)CC3)CC2)ccc1Nc1ncc2ccc(Br)n2n1 | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of example 532 (D), (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-{2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenyl}-amine (0.050 g, 0.00010 mol) and 3-t-Butylsulfamoylphenylboronic acid (0.028 g, 0.00011 mol) were reacted. Purification by prep plate chromatography gave N-tert-Butyl... | COc1cc(N2CCC(N3CCN(C)CC3)CC2)ccc1Nc1ncc2ccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)n2n1 | null | 50.6 | null |
63,802 | ord_dataset-b1bf0950b5cb430abbb1d80744f5df84 | null | 1980-01-01T00:03:00 | true | [Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[C:3]=1[O:21][CH3:22].[OH-].[Na+].[CH:25](O)=O>C=O>[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([CH3:25])[CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]([... | O=CO | COc1cc2c(c(Cl)c1OC)CCNCC2c1ccccc1 | null | C=O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 3.7 g of 6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine in 15 ml of formic acid and 10 ml of formaldehyde is refluxed for 18 hours. The reaction mixture is evaporated to dryness, 20 ml of 6N hydrochloric acid is added and the solution is again evaporated to dryness to give a liquid. T... | COc1cc2c(c(Cl)c1OC)CCN(C)CC2c1ccccc1 | null | null | null |
67,436 | ord_dataset-b5f1497361c94e5fa55257200189a6a4 | null | 1980-01-01T00:06:00 | true | [C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH2:9](O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]C>CO>[C:1]([O:7][CH2:8][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4] | COC(=O)CC(C)=O | CCCCCCCCCCCCO | 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 | 165 | 8 | Introduced into a reactor equipped with a stirrer mechanism, a Vigreux column with a column head and a reflux condenser are 464 g (4 moles) of methyl acetoacetate and 186 g of dodecyl alcohol. The temperature of the reaction medium is progressively raised to 165° C. and the methanol having formed is distilled until the... | CCCCCCCCCCCCOC(=O)CC(C)=O | null | null | null |
957,087 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10]1)=[O:7].N1(CCN)CCC[CH2:22]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH2:14][CH2:22][CH2:13][CH2:12]1)=[O:7... | COc1cc(C(=O)N[C@@H]2CCN(C)C2)ccc1[N+](=O)[O-] | NCCN1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by an analogous method to the preparation of Intermediate 188, on a 9.28 mmol scale utilising 2-pyrrolidin-1-ylethanamine (Aldrich; 1.06 g, 9.28 mmol), as a brown solid (2.3 g, 85%) | COc1cc(C(=O)NCCN2CCCC2)ccc1[N+](=O)[O-] | null | null | null |
1,763,848 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]([CH:13]1[CH2:17][O:16][C:15](=[O:18])[NH:14]1)([CH3:12])[CH3:11].[H-].[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:14]2[CH:13]([C:10]([F:9])([CH3:12])[CH3:11])[CH2:17][O:16][C:15]2=[O:18])[CH:5]=[CH:4][N:3]=1 | CC(C)(F)C1COC(=O)N1 | Clc1ccnc(Cl)n1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | To the solution of 2,4-dichloropyrimidine (150 mg, 1.006 mmol) and 4-(2-fluoropropan-2-yl)oxazolidin-2-one (148 mg, 1.01 mmol) in DMF (4.5 mL), sodium hydride (60% wt. 89 mg, 2.21 mmol) was added to give a pale yellow mixture. The mixture was stirred at room temperature for 2 hr, diluted with EtOAc and stirred for addi... | CC(C)(F)C1COC(=O)N1c1ccnc(Cl)n1 | null | 57.4 | null |
1,453,433 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl[C:2]1[C:3]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:4][C:5]([C:8]2[C:13]([Cl:14])=[CH:12][N:11]=[C:10]([F:15])[CH:9]=2)=[CH:6][N:7]=1.[CH3:24]B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>COCCOC>[Cl:14][C:13]1[C:8]([C:5]2[N:4]=[C:3]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3... | Fc1cc(-c2cnc(Cl)c(NCC3CCOCC3)n2)c(Cl)cn1 | CB(O)O | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | ClCCl | null | null | null | null | null | null | null | null | null | 105 | 0.33 | 3-chloro-6-(5-chloro-2-fluoropyridin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (0.0275 g, 0.077 mmol), methylboronic acid (0.014 g, 0.231 mmol), and sodium carbonate (0.100 ml, 0.200 mmol, 2M aq solution) were dissolved in DME (1.0 ml). The solution was then degassed by sparging with argon for 5 min. It... | Cc1ncc(-c2cc(F)ncc2Cl)nc1NCC1CCOCC1 | null | 191.6 | null |
21,652 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | C(O[CH:5]([CH3:8])[CH:6]=O)(=O)C.[C:9]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:13][C:11]1[O:12][C:5]([CH3:8])=[CH:6][C:10]=1[C:9]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14] | CC(=O)CC(=O)Nc1ccccc1 | CC(=O)OC(C)C=O | null | Cc1ccc(S(=O)(=O)O)cc1 | 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 | null | null | A solution of 24 parts of α-acetoxypropionaldehyde, 35.4 parts of acetoacetanilide and 2 parts of p-toluenesulfonic acid in 100 parts of benzene is kept for 3 hours at 40° C and then boiled under reflux for 1 hour. Adopting the isolation procedure described in Example 1 there is obtained 41.8 parts of 2,5-dimethylfuran... | Cc1cc(C(=O)Nc2ccccc2)c(C)o1 | null | null | null |
1,105,968 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | Br[CH2:2][CH2:3][CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:18]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:19][C:6]1=2.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH:32]2[CH3:37])=[CH:27][CH:26]=1.[I-].[K+]>C(O)(C)C>[Cl:24][C:25]1[CH:26]=[CH:27... | CC1CNCCN1c1ccc(Cl)cc1 | CC(C)(O)c1ccc2c(c1)C(=CCCBr)c1cccnc1CO2 | null | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 80 | 5 | A solution of 2-[5-(3-Bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.24 g, 0.64 mmol) in isopropanol (5 mL) was treated with 1-(4-Chloro-phenyl)-2-methyl-piperazine (0.25 g, 1.2 mmol) and catalytic potassium iodide. The solution was stirred at 80° C. for 5 hr, and evaporated i... | CC1CN(CCC=C2c3cc(C(C)(C)O)ccc3OCc3ncccc32)CCN1c1ccc(Cl)cc1 | null | 68.2 | null |
1,288,012 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | CS[C:3]1[N:4]=[C:5]([CH2:12][C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[NH:6][C:7](=[O:11])[C:8]=1[C:9]#[N:10].[NH:18]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1>>[OH:24][CH:21]1[CH2:22][CH2:23][N:18]([C:3]2[N:4]=[C:5]([CH2:12][C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[NH:6][C:7](=[O:11])[C:8]=2[C:9]#[N:10])[CH2:19][CH2:... | OC1CCNCC1 | CSc1nc(Cc2ccsc2)[nH]c(=O)c1C#N | null | null | null | null | null | null | null | 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 preparation of Example 1, 100 mg (0.38 mmol) of 4-(methylsulphanyl)-6-oxo-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile are reacted with 384 mg (3.80 mmol) of piperidin-4-ol to give 47 mg (39% of theory) of the title compound. | N#Cc1c(N2CCC(O)CC2)nc(Cc2ccsc2)[nH]c1=O | null | null | null |
672,712 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [OH-].[Na+].C([O:5][C:6](=[O:34])[CH2:7][S:8][C:9]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]2[C:10]=1[C:11](=[O:33])[CH:12]=[C:13]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[N:14]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C>CCO>[NH:26]([C:13]1[N:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]2[C:... | CCOC(=O)CSc1nc(C)cc2c1c(=O)cc(Nc1ccccc1)n2-c1ccccc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 4 | Aqueous NaOH (2N, 1 mL) was added to a stirred solution of ethyl[(2-anilino-7-methyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridin-5-yl)sulfanyl]acetate (100 mg, 0.23 mmol) in EtOH (8 mL) at room temperature. The mixture was allowed to stir for 4 h and was concentrated in vacuo. The reaction mixture was acidified with 1N... | Cc1cc2c(c(SCC(=O)O)n1)c(=O)cc(Nc1ccccc1)n2-c1ccccc1 | null | 58.3 | null |
1,493,270 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([C@@H:7]([NH2:11])[CH2:8][S:9][CH3:10])[CH2:4][O:3]1.C([BH3-])#N.[Na+].[CH2:17]([O:24][CH2:25][N:26]1[C:34]2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[N:32][CH:31]=[N:30][C:29]=2[C:28]([CH:40]=O)=[CH:27]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][CH2:25][... | CC(C)(C)Oc1ncnc2c(C=O)cn(COCc3ccccc3)c12 | CSC[C@H](N)[C@@H]1COC(C)(C)O1 | null | [BH3-]C#N | [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 | 25 | 2 | A mixture of the product from Example 27.4 (0.130 g, 0.68 mmol), sodium cyanoborohydride (0.071 g, 1.13 mmol) and 5-(benzyloxymethyl)-4-tert-butyloxy-5H-pyrrolo[3,2-d]pyrimidin-7-carbaldehyde (0.192 g, 0.57 mmol) were evaporated from methanol (3×). The residue was dissolved in methanol (10 ml) and acetic acid added (5 ... | CSC[C@H](NCc1cn(COCc2ccccc2)c2c(OC(C)(C)C)ncnc12)[C@@H]1COC(C)(C)O1 | null | 92.7 | null |
1,065,054 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]([NH2:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][CH2:17][C:18](OC(C)C)=[O:19].S(=O)(=O)(O)O>O>[C:1]([O:5][C:6]1[CH:7]=[C:8]([C@H:12]([NH:14][C:18](=[O:19])[CH2:17][O:16][CH3:15])[CH3:13])[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3] | CC(N)c1cccc(OC(C)(C)C)c1 | COCC(=O)OC(C)C | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 16 | 1-(3-tert-Butoxyphenyl)ethylamine (86 g, 0.45 mol) was admixed with isopropyl methoxyacetate (129 g, 0.98 mol) and Novozyme® 435 (0.9 g), and stirred at room temperature for 16 h. The subsequent analysis of the optical purity showed that the S enantiomer of 1-(3-tert-butoxyphenyl)ethylamine was enantiomerically pure. T... | COCC(=O)N[C@H](C)c1cccc(OC(C)(C)C)c1 | null | 58.6 | null |
151,650 | ord_dataset-772de90433b44abbbacf9b316b845c31 | null | 1986-01-01T00:12:00 | true | [OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N12CCN(CC1)CC2.CN(C)C=O.[CH3:27][N:28]([CH3:32])[C:29](Cl)=[S:30]>O>[CH3:27][N:28]([C:29](=[S:30])[O:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:32] | COC(=O)c1ccc(OC)cc1O | CN(C)C(=S)Cl | null | C1CN2CCN1CC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 50 | 7 | To a mixture of 350 g of methyl 2-hydroxy-4-methoxybenzoate, 648 g of 1,4-diazabicyclo[2.2.2]-octane (DABCO) and 3 L of dimethylformamide was added 712 g of dimethylthiocarbamoyl chloride. The mixture was warmed to 50° C. and held for 7 hours, then allowed to cool overnight. The mixture was poured into 10 L water; the ... | COC(=O)c1ccc(OC)cc1OC(=S)N(C)C | null | 76.5 | null |
12,959 | ord_dataset-a0071d97083e4e69ae8872417ed2776b | null | 1976-01-01T00:09:00 | true | C([N:8]1[CH2:13][CH2:12][C:11]([OH:23])([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>[Pd].CO>[OH:23][C:11]1([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1 | OC1(c2ccc3c(c2)OCO3)CCN(Cc2ccccc2)CC1 | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 39.4 g. 1-benzyl-4-hydroxy-4-(3.4-methylene dioxy phenyl)-piperidine are dissolved in 400 ml. methanol and the solution is mixed with 30 ml. 4-N hydrochloric acid. To this mixture is then added 3 g. of a palladium/carbon catalyst which has been suspended in 60 ml. alcohol. The mixture is hydrogenized at 35° - 40°C unde... | OC1(c2ccc3c(c2)OCO3)CCNCC1 | null | null | null |
808,718 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [O:1]=[S:2]1(=[O:29])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:16](OCC3C=CC([N+]([O-])=O)=CC=3)=[O:17])[CH:13]=[CH:14][C:3]1=2.[CH2:30]([NH:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1)[CH3:31].C(N(CC)CC)C>CCOC(C)=O.CN(C)C1C=CN=CC=1>[O:29]=[S:2]1(=[O:1])[C:6]2[CH:7]=[CH:8][CH:9]... | O=C(Nc1ccc2c(c1)-c1ccccc1S2(=O)=O)OCc1ccc([N+](=O)[O-])cc1 | CCNCc1ccncc1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 18 | 5,5-Dioxo-2-(4-nitrobenzoxycarbonylamino)dibenzothiophene (Example 24; 0.396 g, 1 mmol) was dissolved in EtOAc (10 ml) and treated with 4-(ethylaminomethyl)pyridine (0.150 g, 1.1 mmol), triethylamine (0.202 g, 2 mmol) and 4-(dimethylamino)pyridine (0.006 mg, 0.05 mmol). The reaction was stirred for 18 hours and the sus... | CCN(Cc1ccncc1)C(=O)Nc1ccc2c(c1)-c1ccccc1S2(=O)=O | null | null | null |
231,862 | ord_dataset-67c9ee844bf341888b345c8e36183b40 | null | 1991-01-01T00:07:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH:7]=[C:8]([P:12]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]1)[C:9]([CH3:11])=O)([O-:3])=[O:2].[CH2:22]([N:29]([CH2:31][CH2:32][O:33][C:34](=[O:39])/[CH:35]=[C:36](\[NH2:38])/[CH3:37])[CH3:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[CH3:37][C:36]1... | C/C(N)=C/C(=O)OCCN(C)Cc1ccccc1 | CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)P1(=O)OCCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3.11 grams of 2-(1-(3-nitrobenzylidene)-acetonyl)-2-oxo-1,3,2-dioxaphosphorinane and 2.48 grams of 2 -(N-benzyl-N-methylamino)ethyl3-aminocrotonate was dissolved in 30 ml of isopropanol and the mixture was heated to reflux for eight hours. The reaction solution was concentrated in vacuo and the residue was... | CC1=C(C(=O)OCCN(C)Cc2ccccc2)C(c2cccc([N+](=O)[O-])c2)C(P2(=O)OCCCO2)=C(C)N1 | null | 59.2 | null |
1,562,609 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[CH:9](OC)=[O:10]>C(N(CC)CC)C>[CH:9]([NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])=[O:10] | COC=O | CCOC(=O)CN | null | Cl | 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 | 25 | null | To a 5 L three neck round bottom flask equipped with a mechanic stirrer, a pressure-equalizing funnel and a condenser bearing a calcium chloride drying tube was added glycine ethyl ester hydrochloride (500 g, 3.583 mol) and methyl formate (1.8 L). The suspension was brought to reflux and triethylamine (556 mL) was adde... | CCOC(=O)CNC=O | null | 93 | null |
1,495,661 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [NH2:1][N:2]1[N:11]=[C:10]([S:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:20].[F:21][C:22]1[CH:23]=[C:24]([CH2:29][C:30](O)=[O:31])[CH:25]=[C:26]([F:28])[CH:27]=1>>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([S:12][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[... | Nn1nc(Sc2ccc(Br)cc2)c2ccccc2c1=O | O=C(O)Cc1cc(F)cc(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product from Example 195B and 2-(3,5-difluorophenyl)acetic acid were processed using a method similar to that described in Example 10C to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ 11.76 (s, 1H), 8.39-8.32 (m, 1H), 8.08-8.04 (m, 1H), 8.02 (ddd, J=8.1, 7.6, 1.3, 1H), 7.95 (td, J=8.2, 1.3, 1H), 7.59-7.52 ... | O=C(Cc1cc(F)cc(F)c1)Nn1nc(Sc2ccc(Br)cc2)c2ccccc2c1=O | null | null | null |
1,337,616 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [C:1]([C:3]([S:13][CH2:14][CH3:15])=[CH:4][C@@H:5]1[C@@H:7]([C:8](O)=[O:9])[C:6]1([CH3:12])[CH3:11])#[N:2].S(Cl)([Cl:18])=O>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([C:3]([S:13][CH2:14][CH3:15])=[CH:4][C@@H:5]1[C@@H:7]([C:8]([Cl:18])=[O:9])[C:6]1([CH3:12])[CH3:11])#[N:2] | CCSC(C#N)=C[C@@H]1[C@@H](C(=O)O)C1(C)C | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 65 | 4 | To methyl=(1R)-trans-3-[(1EZ)-2-cyano-2-(ethylthio)ethenyl]-2,2-dimethylcyclopropanecarboxylic acid (8.98 g, 39.9 mmol), toluene (25 mL) was added and then thionyl chloride (5.0 g, 42.0 mmol) was added. Furthermore, N,N-dimethylformamide (50 mg) was added, followed by stirring at an inner temperature of 60 to 70° C. fo... | CCSC(C#N)=C[C@@H]1[C@@H](C(=O)Cl)C1(C)C | null | 98.9 | null |
578,488 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl.[CH2:23](N=C=NCCCN(C)C)C>CO.ClCCl>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O:21][CH3:23])=[O:20])[CH:14]=2)[CH:4]=[C:3]([O:2][CH3:1]... | COc1cc(-c2ccnc(C(=O)O)c2)cc(OC)c1OC | CCN=C=NCCCN(C)C | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 25 | 3 | 4-(3,4,5-Trimethoxyphenyl)pyridine-2-carboxylic acid (587 mg) was dissolved in methanol (2 mL) and dichloromethane (8 mL), and to the solution 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (583 mg) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrate... | COC(=O)c1cc(-c2cc(OC)c(OC)c(OC)c2)ccn1 | null | null | null |
901,856 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:30])=[C:6]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH:14]=[CH:13]2)[CH:7]=1.Cl[C:32]([F:38])([F:37])C(OC)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[F:37][CH:32](... | COC(=O)C(F)(F)Cl | CC(C)(CC(O)(Cn1ccc(=O)c2ccccc21)C(F)(F)F)c1cc(F)ccc1O | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 60 | null | A mixture of 1-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (0.05 g), methyl 2-chloro-2,2-difluoroacetate (0.014 mL) and cesium carbonate (0.195 g) in 1.5 mL of DMF was heated at 60° C. for 20 hours, cooled to room temperature, diluted with ethyl acetate, and washed with a... | CC(C)(CC(O)(Cn1ccc(=O)c2ccccc21)C(F)(F)F)c1cc(F)ccc1OC(F)F | null | null | null |
38,525 | ord_dataset-de10a15943a54ac7a3c3e1c774d21392 | null | 1978-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:5].[CH:18](O)=[O:19]>>[Cl:17][C:14]1[CH:15]=[CH:16][C:2]([NH:1][CH:18]=[O:19])=[C:3]([CH:13]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:5] | O=CO | Nc1ccc(Cl)cc1C(=O)c1ccccc1Cl | null | null | null | null | null | null | null | 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-Amino-5,2'-dichlorobenzophenone is reacted with formic acid, whereby 5, 2'-dichloro-2-formylaminobenzophenone (pale yellow granules melting at 106° to 107° C) is obtained. The product is then reacted with hydrazine hydrate, whereby 3-amino-6-chloro-4-(2-chlorophenyl)-3,4-dihydro-4-hydroxyquinazoline (colorless granul... | O=CNc1ccc(Cl)cc1C(=O)c1ccccc1Cl | null | null | null |
404,360 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | [CH3:1][C:2](=[CH2:54])[C:3]([NH:5][C:6]1[N:7]=[C:8]([CH2:51][CH2:52][CH3:53])[N:9]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:10]=1[C:11]([O-:13])=[O:12])=[O:4].Cl.[CH2:56](O)[CH3:57]>... | CCO | C=C(C)C(=O)Nc1nc(CCC)n(Cc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1C(=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 | To 250 mg of ethyl ,4-[N-(2-methylacryloyl)amino]-2-n-propyl-1-[[2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylate was added 10 mL of 2N--HCl-ethanol (1:1) and the mixture was stirred at an external temperature of 90° C. for 4 hours. The solvent was then distilled off under reduced pressur... | C=C(C)C(=O)Nc1nc(CCC)n(Cc2ccc(-c3ccccc3-c3nnn[nH]3)cc2)c1C(=O)OCC | null | 42 | null |
114,592 | ord_dataset-87aeeef7c91d4312a992c5cea936705c | null | 1984-01-01T00:02:00 | true | [Na].Cl.[C:3]1([CH3:11])[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][NH2:10])[CH:4]=1.C(O[CH2:15][CH2:16][C:17]#[N:18])C>C(O)C>[NH2:18][C:17]1[CH2:16][CH2:15][N:9]([C:5]2[CH:4]=[C:3]([CH3:11])[CH:8]=[CH:7][CH:6]=2)[N:10]=1 | CCOCCC#N | Cc1cccc(NN)c1 | null | Cl | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 0.08 | A 2.8 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 15.8 g. of m-tolylhydrazine hydrochloride is added followed in 5 minutes by 9.9 g. of β-ethoxypropionitrile. The reaction mixture is refluxed for 16 hours, then is evaporated to dryness in vacuo. Water is added and the precipitate is coll... | Cc1cccc(N2CCC(N)=N2)c1 | null | null | null |
1,750,161 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | C(O[C:4]([C:6]1[C:7]2[CH2:15][CH2:14][CH2:13][CH2:12][C:8]=2[S:9][C:10]=1[NH2:11])=[O:5])C.[CH3:16][O:17][CH2:18][C:19]#[N:20]>O1CCOCC1.Cl>[CH3:16][O:17][CH2:18][C:19]1[N:20]=[C:4]([OH:5])[C:6]2[C:7]3[CH2:15][CH2:14][CH2:13][CH2:12][C:8]=3[S:9][C:10]=2[N:11]=1 | CCOC(=O)c1c(N)sc2c1CCCC2 | COCC#N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 20 | To a stirred mixture of 2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester (2.0 g, 0.0088 mol) and methoxyacetonitrile (1.3 ml, 0.0177 mol) in 1,4-dioxane (200 nml), dry HCl gas was purged for 30-45 minutes at 0-5° C. The reaction mixture was then warmed to room temperature and stirred for about... | COCc1nc(O)c2c3c(sc2n1)CCCC3 | null | null | null |
1,615,026 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10]C(OC(C)(C)C)=O)=[CH:5][CH:4]=1.[Cl:18][C:19]1[C:24]([C:25]([N:27]=[C:28]=[O:29])=O)=[C:23]([F:30])[C:22]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:21][CH:20]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:31][NH:32][C:33]... | COc1ccc(NNC(=O)OC(C)(C)C)cc1 | CC(C)(C)C(=O)NCc1ccc(Cl)c(C(=O)N=C=O)c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by following the procedure as described for Example-83 by using tert-butyl 2-(4-methoxyphenyl)hydrazinecarboxylate (Intermediate-55, 0.060 g, 0.21 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate (Intermediate-51, 0.101 g, 0.32 mmol), DCM (10 mL) and TFA (3 mL) to afford 0... | COc1ccc(-n2nc(-c3c(Cl)ccc(CNC(=O)C(C)(C)C)c3F)[nH]c2=O)cc1 | null | null | null |
430,411 | ord_dataset-2d21ceeb77844edc9eaedb2fabca2ff1 | null | 1999-01-01T00:04:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].[C:10]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][O:12][CH2:11]1.O>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH:6][C:14](=[O:15])[CH2:13][O:12][CH2:11][C:10]([OH:17])=[O:16] | O=C1COCC(=O)O1 | Cc1cccc(CN)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 1 | N-(3-methylbenzyl)-diglycolic acid, monoamide was prepared as follows: 2.4 g (0.02 moles) of 3-methylbenzylamine (Aldrich Chemical) was added to 3.0 g (0.026 mole) of diglycolic anhydride (Aldrich) dissolved in 15 mL dioxane. The solution was warmed, with stirring, at 70°-80° C. for 60 min. After cooling slightly, wate... | Cc1cccc(CNC(=O)COCC(=O)O)c1 | null | null | null |
1,738,946 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Cl:1][C:2]1[C:3]([F:42])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][C:32]=2[O:40][CH3:41])=[O:29])[CH:5]=[CH:6][CH:7]=1.C(... | COc1cc(C(=O)O)ccc1NC(=O)[C@@H]1N[C@@H](CC(C)(C)C)[C@](C#N)(c2ccc(Cl)cc2F)[C@H]1c1cccc(Cl)c1F | OCCOCCO | null | O=C1OCCN1P(=O)(Cl)N1CCOC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 8 | To a suspension of chiral 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid (150 mg, 0.243 mmol) in methylene chloride (8 mL) was added triethylamine (72.0 mg, 0.10 mL, 0.717 mmol) followed by bis(2-oxo-3-oxazolidinyl)phosphinic ... | COc1cc(C(=O)OCCOCCO)ccc1NC(=O)[C@@H]1N[C@@H](CC(C)(C)C)[C@](C#N)(c2ccc(Cl)cc2F)[C@H]1c1cccc(Cl)c1F | null | 23.8 | null |
533,549 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [Mg].[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5]Cl.CN(C)[CH:14]=[O:15].Cl>C(OCC)C>[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5][CH:14]=[O:15] | CN(C)C=O | ClCc1c(Cl)cccc1Cl | null | Cl | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A 200-mL three-necked flask equipped with a thermometer, a dropping funnel, a three-way stopcock, and a mechanical stirrer was purged with nitrogen. Thereto, were added 1.85 g (76 mmol) of magnesium, and 30 mL of diethyl ether. The dropping funnel was filled with a solution of 13.5 g (69 mmol) of 2,6-dichlorobenzyl chl... | O=CCc1c(Cl)cccc1Cl | null | 62.3 | null |
286,912 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([S:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:6][C:7](=[O:26])[N:8]2[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)[CH3:2]>O1CCOCC1.O.Cl>[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C... | CCc1cc2c(c(Sc3ccccc3)cc(=O)n2Cc2ccc(C(=O)OC)cc2)c(CC)n1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | Methyl 4-[(5,7-diethyl-2-oxo-4-phenylthio-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]benzoate (200 mg) was dissolved in a mixture of dioxan (4 ml), water (1 ml) and concentrated hydrochloric acid (1 ml) and the mixture was heated at reflux for 4 hours. Volatile material was then removed by evaporation and toluene was add... | CCc1cc2c(c(Sc3ccccc3)cc(=O)n2Cc2ccc(C(=O)O)cc2)c(CC)n1 | null | 61.9 | null |
1,643,945 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | O.[NH2:2]N.C[N:5](/[CH:7]=[N:8]/[C:9]([C:11]1[C:19]2[N:18]=[C:17]([CH3:20])[N:16]([CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[C:15]=2[CH:14]=[C:13]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:12]=1)=O)C.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[CH3:20][C:17]1[N:16]([CH2:2... | Cc1nc2c(C(=O)/N=C/N(C)C)cc(N3CCOCC3)cc2n1Cc1cccc2ccccc12 | NN | null | O=C([O-])[O-] | [Na+] | 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 | 130 | 0.5 | Hydrazine hydrate (3 mL) was added to a solution of N-[(1E)-(dimethylamino)methylidene]-2-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carboxamide (130 mg, 0.29 mmol) in acetic acid (10 mL) and stirred at 130° C. for 30 min. The reaction mixture was cooled to rt and poured into saturated Na2CO3 ... | Cc1nc2c(-c3nc[nH]n3)cc(N3CCOCC3)cc2n1Cc1cccc2ccccc12 | null | 72 | null |
1,470,357 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | C(OC(=O)[NH:5][C:6]([CH3:11])([CH3:10])[CH2:7][CH2:8][NH2:9])C.[BrH:13]>C(O)(=O)C>[BrH:13].[BrH:13].[CH3:10][C:6]([NH2:5])([CH3:11])[CH2:7][CH2:8][NH2:9] | CCOC(=O)NC(C)(C)CCN | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | 2.8 g of ethyl(3-amino-1,1-dimethylpropyl)carbamate are cooled with an ice bath. 9.9 mL of 33% HBr in acetic acid are added dropwise and then the mixture is refluxed with heating for 2 h. After returning to RT, the product is precipitated with Et2O, and filtered. The obtained powder is dried in the oven at 70° C. 2.34 ... | CC(C)(N)CCN | null | 55 | null |
1,681,391 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | C([O:8][C@H:9]1[CH2:12][C@H:11]([O:13][C:14]2[CH:45]=[CH:44][C:17]([CH2:18][C@H:19]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:20][C@@H:21]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:16][CH:15]=2)[CH2:10]1)C1C=CC=CC=1>CO.... | CC(C)(C)OC(=O)N[C@@H](C[C@H](Cc1ccc(O[C@H]2C[C@H](OCc3ccccc3)C2)cc1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 43 mg (0.07 mmol) of di-tert-butyl (4S)-4-(4-{trans-[3-(benzyloxy)cyclobutyl]oxy}benzyl)-N-(tert-butoxycarbonyl)-L-glutamate were dissolved in 10 mL of methanol and under argon atmosphere palladium (10% on charcoal) was added and the suspension hydrogenated overnight at room temperature. The reaction mixture was filter... | CC(C)(C)OC(=O)N[C@@H](C[C@H](Cc1ccc(O[C@H]2C[C@H](O)C2)cc1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | null | null | null |
1,768,686 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][CH:15]([C:17]([F:20])([F:19])[F:18])[N:14]3[N:21]=[C:22]([C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=4)[C:27](O)=[O:28])[CH:23]=[C:13]3[NH:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N:33]1([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:38][CH2:37][NH:36][CH2:3... | COc1ccc(C2CC(C(F)(F)F)n3nc(-c4cccc(C(=O)O)c4)cc3N2)cc1OC | CC(C)(C)OC(=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 | Example ER-896388 was prepared in two steps from 3-(5-(3,4-dimethoxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-yl)benzoic acid (25 mg, 0.056 mmol) and commercially available tert-butyl piperazine-1-carboxylate (42 mg, 0.224 mmol) in a manner similar to that of example D-6 to afford interme... | COc1ccc(C2CC(C(F)(F)F)n3nc(-c4cccc(C(=O)N5CCN(C(=O)OC(C)(C)C)CC5)c4)cc3N2)cc1OC | null | 51.8 | null |
505,502 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [N+](C1C=CC([O:10][C:11]([N:13]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[C:17]([C:27]([O:29][CH3:30])=[O:28])=[C:16]([CH2:31][O:32][CH3:33])[NH:15][C:14]2=[O:34])=O)=CC=1)([O-])=O.[C:35]1([C:41]2([C:51]3[O:52][CH:53]=[CH:54][CH:55]=3)[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][CH2:49][NH2:50])[... | NCCCN1CCC(c2ccccc2)(c2ccco2)CC1 | COCC1=C(C(=O)OC)C(c2ccc(F)c(F)c2)N(C(=O)Oc2ccc([N+](=O)[O-])cc2)C(=O)N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 6-(3,4-difluorophenyl)-4-methoxymethyl-2-oxo-3,6-dihydro-2H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl)ester (20 mg, 0.04 mmol) in 2 ml of CH2Cl2 was added 3-(4-phenyl-4-furan-2-yl-piperidin-1-yl)-propylamine (12 mg, 0.04 mmol) and resulting solution was stirred for 2 h at 25° C. ... | COCC1=C(C(=O)OC)C(c2ccc(F)c(F)c2)N(C(=O)NCCCN2CCC(c3ccccc3)(c3ccco3)CC2)C(=O)N1 | null | 88.3 | null |
23,885 | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | null | 1977-01-01T00:05:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5](OC)=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>C1(C)C(C)=CC=CC=1>[C:2]1([C:15]2[C:14]([C:17]3[C:22]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=[CH:11][CH:16]=2)[CH:7]=[CH:6][CH:5... | Brc1ccc(-c2ccccc2)cc1 | COc1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | The reaction is carried out as in Example 9 except that the 18.7 parts of 4-bromoanisole are replaced by 23.3 parts of 4-bromobiphenyl, and 110 parts of xylene are added as a solvent. After the reflux period, the reaction mixture is not steam distilled, but is cooled, and the solids present are collected by filtration,... | c1ccc(-c2ccccc2-c2ccccc2-c2ccccc2)cc1 | null | null | null |
1,519,419 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH2:13][OH:14])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=1.[OH-].[Na+].Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]>CCOC(C)=O>[Cl:27][C:26]([Cl:29])([Cl:28])[CH2:25][O:24][C:22](=[O:23])[NH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][... | CC(C)(C)c1cc(N)n(-c2cccc(CO)c2)n1 | O=C(Cl)OCC(Cl)(Cl)Cl | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 1.25 | To a bi-phasic mixture of Intermediate 29b (737 mg, 3.00 mmol) in EtOAc (22.5 mL) and 1N NaOH solution (8.11 mL, 8.11 mmol) at 0° C. was added 2,2,2-trichloroethyl chloroformate (0.45 mL, 3.30 mmol) and the mixture stirred for 1.25 h. The layers were separated and the organic layer was washed with brine, dried and conc... | CC(C)(C)c1cc(NC(=O)OCC(Cl)(Cl)Cl)n(-c2cccc(CO)c2)n1 | null | 99.8 | null |
441,011 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19][C:20]4[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][CH:21]=4)[CH:16]=3)[O:11][C:10]([CH3:32])([CH3:31])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]... | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(c2ccc(C)cc2)=CC(C)(C)O3)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCO | null | null | null | null | null | null | null | null | null | 35 | 8 | To a solution of ethyl 4-[[4-(4-methylphenyl)-2,2-dimethyl-(2H)chromen-6-yl]-ethynyl]-benzoate (Compound 266, 90.0 mg, 0.213 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (120.0 mg, 3.0 mmol, 3.0 mL of a 1M aqueous solution). The resulting solution was heated to 35° C., cooled to room temperature and stirred overn... | Cc1ccc(C2=CC(C)(C)Oc3ccc(C#Cc4ccc(C(=O)O)cc4)cc32)cc1 | null | 83.3 | null |
202,486 | ord_dataset-19e5fc80c1554f4f8641c835e055f02b | null | 1990-01-01T00:01:00 | true | S(O)(O)(=O)=O.[NH2:6][C:7]([CH3:19])([CH3:18])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1.C(O)C.NN>[Ni]>[NH2:6][C:7]([CH3:19])([CH3:18])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1 | CC(C)(N)Cc1ccc([N+](=O)[O-])cc1 | null | null | [Ni] | NN | O=S(=O)(O)O | 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 | 40 | 0.02 | 2-Amino-2-methyl-1-(4-nitrophenyl)propane sulfate (6.07 g, 25 mmol) was suspended in ethanol (33 ml, 50 mmol) was added with stirring. Hydrazine (2.5 g, 78 mmol) was added, followed by Raney nickel (0.2 ml of 50% slurry). After 1 min gas evolution began, and the mixture turned yellow and was warmed to about 40° C. Afte... | CC(C)(N)Cc1ccc(N)cc1 | null | null | null |
59,441 | ord_dataset-28b19b59e93c47698a5a2b21048ec201 | null | 1979-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH:13]([C:15]2([CH2:18][CH3:19])[CH2:17][CH2:16]2)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Br)(Br)[Br:21].[Br-].[Li+]>[Br-].[Zn+2].[Br-]>[CH2:18]([C:15](=[CH:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:16][CH2:17][Br:21])[CH3:1... | CCC1(C(O)CCc2ccc(OC)c(OC)c2)CC1 | BrP(Br)Br | null | [Br-] | [Li+] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-Ethyl-6-(3,4-dimethoxyphenyl)-3-hexenyl bromide [V; Ar is 3,4-(CH3O)2C6H3, R is C2H5 ] was prepared from 16 g. of 2-(3,4-dimethoxyphenyl)ethyl 1-ethylcyclopropyl carbinol (Preparation B4), 16.8 g. of phosphorus tribromide, 16.8 g. of lithium bromide and 17.6 g. of zinc bromide according to the procedure given above i... | CCC(=CCCc1ccc(OC)c(OC)c1)CCBr | null | null | null |
110,755 | ord_dataset-406d20cb3f314e2c967b14f55925f895 | null | 1983-01-01T00:10:00 | true | C1CCCCC1.[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH:13](=O)[CH2:14][CH:15]([CH3:17])[CH3:16]>O>[CH3:16][CH:15]([CH3:17])[CH:14]=[CH:13][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1 | C1COCCN1 | CC(C)CC=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCCCC1 | O | null | null | null | null | null | null | null | null | null | 50 | null | Into a 12 liter flask equipped with stirrer, Bidwell trap, thermometer, heating mantle, addition funnel and condenser is placed 2,200 ml of cyclohexane and 2,180 grams (25 moles) of morpholine. The resulting mixture is heated to 50° C. and 2,155 grams of isovaleraldehyde are added over a 1.5 hour period. An exotherm oc... | CC(C)C=CN1CCOCC1 | null | null | null |
1,589,459 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [F:1][C:2]([F:20])([F:19])[C:3]([NH:5][CH2:6][C:7]1([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:4].CCN(CC)CC.[CH:28]1([CH2:31][S:32](Cl)(=[O:34])=[O:33])[CH2:30][CH2:29]1>C(Cl)Cl>[CH:28]1([CH2:31][S:32]([N:16]2[CH2:17][CH2:18][N:13]([C:7]3([CH2:6][NH:5][C:3](=[O:4])[C:2](... | O=S(=O)(Cl)CC1CC1 | O=C(NCC1(N2CCNCC2)CCCCC1)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 3 | To a stirring ice-cold solution of 14 (10.0 g, 34.09 mmol) and Et3N (14.2 mL, 102.27 mmol) in CH2Cl2 (200 mL) was slowly added 1-cyclopropylmethylsulfonyl chloride (5.27 g, 34.09 mmol). The mixture stirred at ambient temperature under an atmosphere of nitrogen for 3 h. The mixture was washed with 2 N NaOH (50 mL), 2 N ... | O=C(NCC1(N2CCN(S(=O)(=O)CC3CC3)CC2)CCCCC1)C(F)(F)F | null | null | null |
445,102 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | [N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]([O:11][CH2:17][CH3:18])=[O:10])=[CH:3][CH:2]=1 | O=C(O)C=Cc1ccncc1 | CCO | 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 | null | null | 3-(4-Pyridyl)acrylic acid (16.18 g, 0.1085 mol) was slurried in 200 ml of absolute ethanol. Concentrated sulfuric acid (8 ml) was added and the reaction was refluxed for 3 hours. After cooling, the solvent was evaporated and the residue was cautiously neutralized with saturated sodium bicarbonate solution. The resultin... | CCOC(=O)C=Cc1ccncc1 | null | 93 | null |
1,023,519 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | I[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].Br[C:13]1[CH:14]=[C:15]([NH2:20])[C:16]([Cl:19])=[N:17][CH:18]=1>>[NH2:20][C:15]1[CH:14]=[C:13]([C:2]2[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=2[CH3:11])[CH:18]=[N:17][C:16]=1[Cl:19] | CC(=O)Nc1nc(C)c(I)s1 | Nc1cc(Br)cnc1Cl | null | null | null | null | null | null | null | 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 an analogous method to that described in Example 7, N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide was reacted with 5-bromo-2-chloropyridin-3-amine to give the title compound (Method A HPLC: retention time 5.5 minutes) in 25% yield; 1H NMR Spectrum: (acetone-d6) 12.17 (1H, br s); 7.68 (1H, d); 7.20 (1H, d); 5.70 (... | CC(=O)Nc1nc(C)c(-c2cnc(Cl)c(N)c2)s1 | null | 25 | null |
850,141 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.CCN(C(C)C)C(C)C.[CH3:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH:33]([OH:41])[CH2:34][N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)=[CH:27][C:25]=2[N:26]=1>CCO>[CH:7]1([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:38]2[CH2:39][CH2:40][... | Cc1nc2cc(OCC(O)CN3CCNCC3)ccc2s1 | BrCCCCOC1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CCO | null | null | null | null | null | null | null | null | null | null | null | A solution of (4-bromobutoxy)cyclopentane (400 mg, 1.81 mmol) in EtOH (5 mL) was treated with DIEA (0.64 mL, 3.62 mmol) and 1-(2-methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol as prepared in Example 3A (557 mg, 1.81 mmol). The solution was stirred at reflux 15 hours. Upon cooling, the product was concentrated ... | Cc1nc2cc(OC[C@H](O)CN3CCN(CCCCOC4CCCC4)CC3)ccc2s1 | null | null | null |
1,410,416 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | Cl[C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[SH:19]>>[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[S:19][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11] | CC(=O)c1cc([N+](=O)[O-])c(Cl)s1 | Cn1ccnc1S | null | null | null | null | null | null | null | 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 procedure described for example 14 from 1-(5-Chloro-4-nitro-2-thienyl)ethanone (0.1 g, 0.49 mmol) and N-methyl imidazole-2-thiol (0.056 g, 0.49 mmol). The title compound was obtained as a solid (50 mg, 36% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.48 (2H, s) 7.64 (2H, dd) 7.28 (2H, dd), 3.42 (3H,... | CC(=O)c1cc([N+](=O)[O-])c(Sc2nccn2C)s1 | null | null | null |
1,172,236 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [C:1]([N:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25]([NH:28][CH3:29])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH:36]1(N)C[CH2:37]1>C1COCC1>[C:1]([N:5]1[CH:9]=[C:8]([NH... | NC1CC1 | CNc1ncc2cc(-c3cc(NC(=O)Nc4cnn(C(C)(C)C)c4)c(F)cc3C)c(=O)n(C)c2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | Using general method E, 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea from Example 109 (0.081 g, 0.16 mmol) and cyclopropanamine (0.027 g, 0.48 mmol) were combined in THF (1 mL) to provide 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-... | Cc1cc(F)c(NC(=O)Nc2cnn(C(C)(C)C)c2)cc1-c1cc2cnc(NC3CC3)nc2n(C)c1=O | null | 63.2 | null |
1,536,321 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([OH:14])=O)[C:6]=2[CH:15]=1.Cl.Cl.[CH3:18][NH:19][CH2:20][C:21]1[NH:25][C:24]2[CH:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[CH:29][C:23]=2[N:22]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CCOC(C)=O.ClCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2... | O=C(O)Cn1c(=O)oc2ccc(Cl)cc21 | CNCc1nc2cc(C(F)(F)F)ccc2[nH]1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 8 | To a mixture of (5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid (300 mg), N-methyl-1-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]methanamine dihydrochloride (420 mg), and dichloromethane (10 mL) were added TEA (552 μL), HOBt (214 mg), and WSC.HCl (303 mg), followed by stirring at room temperature overnight. The react... | CN(Cc1nc2cc(C(F)(F)F)ccc2[nH]1)C(=O)Cn1c(=O)oc2ccc(Cl)cc21 | null | 88.4 | null |
651,838 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([S:15][CH3:16])[N:12]=[C:11](O)[C:10]=1[CH3:18].O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:11]1[C:10]([CH3:18])=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[N:14]=[C:13]([S:15][CH3:16])[N:12]=1 | O=P(Cl)(Cl)Cl | CSc1nc(O)c(C)c(-c2ccc(F)cc2F)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5 | A solution of 5.9 g of 6-(2,4-difluorophenyl)-5-methyl-2-(methylthio)pyrimidin-4-ol in 25 mL of POCl3 was heated to reflux and stirred at this temperature for 5 h. All but ca. 5 mL of POCl3 was removed by vacuum distillation, and the residue was quenched by pouring into 200 mL of ice-water, neutralizing with Na2CO3 and... | CSc1nc(Cl)c(C)c(-c2ccc(F)cc2F)n1 | null | null | null |
1,261,190 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | Cl.Cl.[CH2:3]([O:5][C:6](=[O:35])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([C:16]2[C:17]([CH2:26][NH:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:9]=1)[CH3:4].[C:36](OC(=O)C)(=[O:38])[CH3:37]>>[CH2:3]([O:5][C:6](=[O:35])[CH... | CCOC(=O)Cc1ccc(OC)c(-c2cc3ccccc3nc2CNCc2ccccc2)c1 | CC(=O)OC(C)=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 | Prepared according to the procedure described in Example 5, Step 5, using the following starting materials: {3-[2-(benzylamino-methyl)-quinolin-3-yl]-4-methoxy-phenyl}-acetic acid ethyl ester, dihydrochloride and acetic anhydride. | CCOC(=O)Cc1ccc(OC)c(-c2cc3ccccc3nc2CN(Cc2ccccc2)C(C)=O)c1 | null | null | null |
44,392 | ord_dataset-ff0bcb6c2300494cbdf16005ad32ad5f | null | 1978-01-01T00:08:00 | true | Cl.[CH3:2][NH:3][OH:4].C(N(CC)CC)C.[Cl:12][C:13]1[CH:14]=[C:15]([N:20]=[C:21]=[O:22])[CH:16]=[C:17]([Cl:19])[CH:18]=1>C(Cl)(Cl)Cl>[CH3:2][N:3]([OH:4])[C:21]([NH:20][C:15]1[CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]([Cl:12])[CH:14]=1)=[O:22] | CNO | O=C=Nc1cc(Cl)cc(Cl)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 20 | 5 | A mixture of 10 g of N-methyl-hydroxylamine hydrochloride in 100 ml of chloroform was stirred while 18 ml of triethylamine were added at 0° C. Then, 20 g of 3,5-dichlorophenyl isocyanate in 30 ml of chloroform were added to the mixture at 10° to 15° C and the mixture was stirred for 5 hours at 20° C and was then distil... | CN(O)C(=O)Nc1cc(Cl)cc(Cl)c1 | null | 88 | null |
351,853 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [N:1]1[N:2]([CH2:10][CH2:11]O)[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[N:13]1C=CC=CC=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O>C(OCC)C>[N:1]1[N:2]([CH2:10][CH2:11][NH2:13])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12 | OCCn1nc2ccccc2n1 | c1ccncc1 | null | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | -50 | null | 4.70 g Of the 2-(2-benzotriazolyl)ethanol (28.8 mmol) was dissolved in 200 ml diethyl ether and 2.28 g pyridine (28.8 mmol) was added. The mixture was cooled to -50° C., and 8.18 g triflic anhydride (29 mmol) was added. The mixture was removed from the cooling bath, and was allowed to reach room temperature. The mixtur... | NCCn1nc2ccccc2n1 | null | 44,791.7 | null |
1,559,946 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [N:1]1([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:16][C:17]([F:33])([F:32])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26](O)=[O:27])[N:19]=1>>[NH:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[N:1]1[CH2:6][CH2:5... | O=C(O)c1cccc(-c2noc(C(F)(F)F)n2)c1 | c1ccc2[nH]c(N3CCNCC3)nc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was synthesized from 2-(piperazin-1-yl)-1H-benzo[d]imidazole and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (100 mg, yield 23%). 1H NMR (400 MHz, DMSO-d6) δ 11.49 (br s, 1H), 8.19-8.17 (d, J=8.5 Hz, 1H), 8.11 (s, 1H), 7.76-7.72 (m, 2H), 7.21 (m, 2H), 6.94 (... | O=C(c1cccc(-c2noc(C(F)(F)F)n2)c1)N1CCN(c2nc3ccccc3[nH]2)CC1 | null | 23 | null |
402,040 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH2:20](I)[CH:21]=[CH2:22]>C(O)C.CCOCC>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1)[CH:21]... | CCCC(=O)NC[C@@H]1C[C@H]1c1cccc(O)c1 | C=CCI | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CCO | null | null | null | null | null | null | null | null | null | null | 18 | To a rapidly stirred solution of (trans)-N-[[2-(3-hydroxyphenyl)cyclopropyl]methyl] butanamide (0.8 g, 3.4 mmol) and KOH (210 mg, 3.74 mmol) in ethanol (15 mL) was added allyl iodide (622 mg, 3.7 mmol). After stirring for 18 h, the suspension was diluted with Et2O (100 mL), and washed with H2O, 2N NaOH, brine, dried (K... | C=CCOc1cccc([C@@H]2C[C@H]2CNC(=O)CCC)c1 | null | 34.4 | null |
1,414,941 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:33]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[C:14]([N:16]([CH2:25][CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])[C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[O:15])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>>[NH2:33][C@@H:13]([CH2:... | CCOC(CN(C(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)OCC1c2ccccc2-c2ccccc21)[C@H](C)c1ccccc1)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | According to the procedure described in the synthesis method of Compound IV-1, (9H-fluoren-9-yl)methyl(S)-3-(4-tert-butoxyphenyl)-1-((2,2-diethoxyethyl)((R)-1-phenylethyl)amino)-1-oxopropan-2-ylcarbamate (Compound III-14) (3.08 g, 4.5 mmol) was treated with piperidine and the obtained residue was purified by silica gel... | CCOC(CN(C(=O)[C@@H](N)Cc1ccc(OC(C)(C)C)cc1)[C@H](C)c1ccccc1)OCC | null | 96.8 | null |
1,638,926 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]4N=[CH:24][N:23]=[C:22](N)[C:21]=4[C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[CH2:16][CH2:15]3)[N:11](C)[CH:12]=2)=[CH:4][C:3]=1[C:35]([F:38])([F:37])[F:36].Br[C:40]1C=NC=CC=1N1CCC(C2NC=C(C3C=CC=C(C(F)(F)F)C=3)N=2)CC1>>... | COc1ccc(-c2c(N)ncnc2N2CCC(c3nc(-c4ccc(F)c(C(F)(F)F)c4)cn3C)CC2)cc1 | FC(F)(F)c1cccc(-c2c[nH]c(C3CCN(c4ccncc4Br)CC3)n2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in an analogous manner as 6-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-5-(4-methoxy-phenyl)-pyrimidin-4-ylamine using 3-bromo-4-(4-{4-[3-(trifluoromethyl)phenyl]-1H-imidazol-2-yl}piperidin-1-yl)pyridine instead of 5-bromo-6-(4-{4-[4-fluoro-3-(tri... | COc1ccc(-c2cnccc2N2CCC(c3nc(-c4cccc(C(F)(F)F)c4)c[nH]3)CC2)cc1 | null | null | null |
485,368 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]4[CH:26]=[C:25]([O:27][CH:28]([CH3:32])[C:29]([OH:31])=[O:30])[CH:24]=[CH:23][C:22]=4[CH3:33])[C:17]=3[CH:34]=2)[C:3]1=[O:35].[OH-].[Na+:37]>O>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[C... | Cc1ccc(OC(C)C(=O)O)cc1-c1nsc2ccc(-n3c(=O)cc(C(F)(F)F)n(C)c3=O)cc12 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 2-{{2-{5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}-p-tolyl}oxy}propionic acid (0.500 g) and sodium hydroxide (0.0360 g) in water is stirred at room temperature overnight, concentrated in vacuo to one-half volume, and filtered to give the title product a... | Cc1ccc(OC(C)C(=O)[O-])cc1-c1nsc2ccc(-n3c(=O)cc(C(F)(F)F)n(C)c3=O)cc12 | null | null | null |
1,534,659 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [F:1][C:2]1[C:3]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:4][N:5]([S:14]([C:17]2[O:18][C:19]([CH:22]([OH:24])[CH3:23])=[CH:20][CH:21]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1.C(N(CC)CC)C.Cl>CS(C)=O>[C:22]([C:19]1[O:18][C:17]([S:14]([N:5]2[C:... | CC(O)c1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)c(F)c2-c2cccnc2F)o1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CS(C)=O | null | null | null | null | null | null | null | null | null | 60 | 72 | To a solution of tert-butyl [(4-fluoro-5-(2-fluoropyridin-3-yl)-1-{[5-(1-hydroxyethyl)-2-furyl]sulfonyl}-1H-pyrrol-3-yl)methyl]methylcarbamate (234 mg) in dimethyl sulfoxide (3 mL) were added triethylamine (3 mL) and sulfur trioxide pyridine complex (449 mg), and the mixture was stirred at 60° C. for 3 days. 1 mol/L Hy... | CC(=O)c1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)c(F)c2-c2cccnc2F)o1 | null | 77.2 | null |
1,093,132 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [F:1][CH:2]([F:11])[C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.[OH-].[Na+].[CH3:14][CH:15]=[O:16]>O>[F:11][CH:2]([F:1])[C:3]1[O:4][C:5]([CH:15]([OH:16])[CH3:14])=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1 | CC=O | O=c1cc(C(F)F)occ1O | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To an ice bath cooled suspension of 2-difluoromethyl-5-hydroxy-pyran-4-one (1.00 g, 6.17 mmol), obtained as described in Example 4, in deionized water was added a 6.0M NaOH solution (1.23 mL, 7.40 mmol). A clear dark brown red solution was obtained, and CH3CHO (6.0 mL, 107 mmol) was added dropwise. After 2 hrs, the rea... | CC(O)c1oc(C(F)F)cc(=O)c1O | null | null | null |
842,925 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12](O)=[O:13])=[CH:6][CH:5]=1.C(Cl)(=O)C(Cl)=O.[NH3:22]>O1CCCC1.CN(C)C=O>[F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([NH2:22])=[O:13])=[CH:6][CH:5]=1 | N | O=C(O)C=Cc1ccc(OC(F)F)cc1 | null | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 2.5 | 2 | To a suspension of 8.70 g (40.6 mmol) 3-(4-difluoromethoxy-phenyl)-acrylic acid in 60.0 ml tetrahydrofuran and 0.6 ml N,N-dimethylformamide a solution of 5.14 ml (60.9 mmol) oxalyl chloride in 10 ml tetrahydrofuran was added dropwise at 0° C. within 10 min. Stirring was continued at 0-5° C. for 30 min. and 2 h at room ... | NC(=O)C=Cc1ccc(OC(F)F)cc1 | null | null | null |
692,662 | ord_dataset-35824232b132464aa99e71aba765981d | null | 2005-01-01T00:12:00 | true | [C:1]([NH:4][CH:5]([C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])[CH2:6][C:7]1[CH:31]=[CH:30][C:10]([N:11]([C:21](=[O:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])=[C:9]([CH2:32][CH3:33])[CH:8]=1)(=[O:3])[CH3:2].[C:40]1([C:46]([C:49]2[CH... | C=CCOC(=O)C(Cc1ccc(N(C(=O)C(=O)OC(C)(C)C)c2ccccc2C(=O)O)c(CC)c1)NC(C)=O | [N-]=[N+]=C(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | To 2-{4-[2-(acetylamino)-3-(allyloxy)-3-oxopropyl][tert-butoxy(oxo)acetyl]-2-ethylanilino}benzoic acid in acetone was added diphenyldiazomethane (until all starting material was consumed as evident by monitoring via TLC). The reaction mixture was concentrated under reduced pressure, purified on silica gel using ethyl a... | C=CCOC(=O)C(Cc1ccc(N(C(=O)C(=O)OC(C)(C)C)c2ccccc2C(=O)OC(c2ccccc2)c2ccccc2)c(CC)c1)NC(C)=O | null | null | null |
1,027,765 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[C:16]([F:19])([F:18])[F:17])=[CH:6][CH:5]=1.[CH3:24][CH:25]([C:31]([CH3:33])=O)[C:26](OCC)=[O:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:33][C:31]1[C:25]([CH3:24])=[C:26]([OH:27])[C:14]2[C:12]... | Nc1ccc(Oc2ccc(OC(F)(F)F)cc2)c(C(F)(F)F)c1 | CCOC(=O)C(C)C(C)=O | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 3.4 g of 4-(4-trifluoromethoxyphenoxy)-3-trifluoromethyl-aniline, 2.4 g of ethyl 2-methylacetoacetate, and 0.3 g of p-toluenesulfonic acid dissolved in 100 mL of xylene was heated under reflux for 36 hr. This reaction solution was cooled, and the precipitated crystals were collected by filtration to give ... | Cc1nc2cc(C(F)(F)F)c(Oc3ccc(OC(F)(F)F)cc3)cc2c(O)c1C | null | 41.1 | null |
818,771 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | C(Cl)(=O)C([Cl:4])=O.[CH2:7]([O:9][C:10]([C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:15]2[CH:28]=[CH:29][S:30][C:14]=2[C:13]=1O)=[O:11])[CH3:8].CN(C=O)C>C(Cl)Cl>[CH2:7]([O:9][C:10]([C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])... | CCOC(=O)c1c(O)c2sccc2n(Cc2ccc(OC)cc2)c1=O | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 24 | Oxalyl chloride (4.8 mL, 55 mmol) was added to a solution of 7-hydroxy-4-(4-methoxybenzyl)-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (54) (9.87 g, 27 mmol) in dry CH2Cl2 at 0° C. After adding anhydrous DMF (0.5 mL), the solution was allowed to come at room temperature and was further stirred... | CCOC(=O)c1c(Cl)c2sccc2n(Cc2ccc(OC)cc2)c1=O | null | 85 | null |
125,651 | ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833 | null | 1985-01-01T00:01:00 | true | [CH2:1]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([OH:23])=[O:22])[CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl>C(O)CCC>[CH2:1]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([O:23][CH2:12][CH2:1][CH2:2][CH3:3])=[O:22])[CH:15]=2)[CH2... | CCCCCCCCCCCc1cc2ccc(C(=O)O)cc2[nH]1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-(n-undecyl)indole-6-carboxylic acid (15.0 g) in n-butanol (100 ml) containing aqueous hydrochloric acid (10 ml, of strength 36.5% w/v) was heated on a steam bath for 16 hours. The solution was concentrated in vacuo to approximately half of its volume and the solid which crystallised on cooling was colle... | CCCCCCCCCCCc1cc2ccc(C(=O)OCCCC)cc2[nH]1 | null | 127.9 | null |
1,568,792 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=O)=[CH:6][C:3]=1[C:4]#[N:5].[C:13]([O:17][C:18](=[O:23])[NH:19][CH2:20][CH2:21][NH2:22])([CH3:16])([CH3:15])[CH3:14].[BH3-]C#N.[Na+].C(O)(=O)C>CO>[C:4]([C:3]1[CH:6]=[C:7]([CH2:10][CH2:11][NH:22][CH2:21][CH2:20][NH:19][C:18](=[O:23])[O:17][C:13]([CH3:15])([CH3:14])[CH3:16])[... | CC(C)(C)OC(=O)NCCN | N#Cc1cc(CC=O)ccc1F | null | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 2-fluoro-5-(2-oxoethyl)benzonitrile (1.5 g, 9.2 mmol), tert-butyl(2-aminoethyl)carbamate (1.5 g, 9.2 mmol), NaCNBH3 (1.2 g, 18.4 mmol) and acetic acid (1.6 g, 27.6 mmol) in methanol (20 mL) was stirred at ambient temperature overnight. The solvents were evaporated, and the residue was basified with saturat... | CC(C)(C)OC(=O)NCCNCCc1ccc(F)c(C#N)c1 | null | null | null |
1,735,769 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1N.N([O-])=O.[Na+].[BrH:17]>O>[Br:17][C:3]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:6][C:7]([CH3:9])=[CH:8][C:2]=1[CH3:1] | Cc1cc(C)c(N)c([N+](=O)[O-])c1 | Br | null | O=N[O-] | [Na+] | 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 | 0 | 0.5 | To a suspension of 2,4-dimethyl-6-nitroaniline (5 g, 30.12 mmol) in water (38 mL) was added HBr (15 mL, 40%). The mixture was heated to reflux for 10 minutes and then cooled to 0° C. A solution of NaNO2 (2.07 g) in water (12 mL) was added dropwise with cooling. The mixture was stirred for 30 minutes and then added slow... | Cc1cc(C)c(Br)c([N+](=O)[O-])c1 | null | 26 | null |
1,676,166 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH:4]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([NH2:26])=[O:25])=[CH:19][CH:18]=1>>[ClH:2].[Cl:15][C:11]1[CH:10]=[C:9]([C:5]2[CH:4]=[C:3]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:23][C:24]([NH2:26])=[O:25])=[CH:2... | Clc1cccc(-c2cc(Cl)ccn2)c1 | NC(=O)Cc1ccc(N)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following general procedure A2, 4-chloro-2-(3-chlorophenyl)pyridine hydrochloride (0.115 g, 0.44 mmol) was reacted with 2-(4-aminophenyl)acetamide (0.080 g, 0.53 mmol), followed by formation of the hydrochloride salt to afford the title compound (0.066 g, 40%) as a light yellow solid. MW=374.26. 1H NMR (DMSO-d6, 500 MH... | NC(=O)Cc1ccc(Nc2ccnc(-c3cccc(Cl)c3)c2)cc1 | null | 40.1 | null |
679,178 | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | null | 2005-01-01T00:08:00 | true | [CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][NH2:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][NH:21][S:28]([C:22]2[CH:27]=[CH:26][CH:25]=[... | CCCCc1nc2cnc3ccccc3c2n1CCCN | O=S(=O)(Cl)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the general method of Example 239 Part B, 3-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propylamine (2.00 g, 7.08 mmol) was reacted with benzenesulfonyl chloride (1.38 g, 7.79 mmol) to provide 2.83 g of N-[3-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]benzenesulfonamide as a light red foam. | CCCCc1nc2cnc3ccccc3c2n1CCCNS(=O)(=O)c1ccccc1 | null | 94.6 | null |
139,060 | ord_dataset-7d359d96b3a64882921ebdc6c850e22e | null | 1986-01-01T00:01:00 | true | Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[N:4]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>C(O)C.O>[N:18]1([CH2:2][C:3]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:6]3[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=3[N:4]=2)[CH:22]=[CH:21][N:20]=[CH:19]1 | ClCc1nc2ccccc2n1-c1ccccc1 | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-chloromethyl-1-phenyl-1H-benzimidazole (3.4 g) and imidazole (4.8 g) in ethanol (25 ml) was stirred at 60° C for 7 hours. The reaction mixture was concentrated under reduced pressure to give an oil, which was diluted with water and extracted three times with dichloromethane. The combined extract was was... | c1ccc(-n2c(Cn3ccnc3)nc3ccccc32)cc1 | null | 69 | null |
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