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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
615,753 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | [NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]1.[C:8](OC)(=[O:23])[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[OH:10].C[O-].[Na+].Cl>CO.C1C=CC=CC=1>[C:8]([O:7][CH:3]1[CH2:4][CH2:5][CH2:6][NH:1][CH2:2]1)(=[O:23])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12... | OC1CCCNC1 | COC(=O)C(O)(c1ccccc1)c1ccccc1 | null | C[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | CO | null | null | null | null | null | null | null | null | null | 25 | 3 | 30 ml of benzene, 0.4 g (4 mmol) of 3-piperidinol and 1.0 g (4 mmol) of methyl benzilate were put into a 50 ml 3-mouth flask equipped with a stirrer, a reflux condenser, and a molecular sieve 4A (15 g) tube and a soda lime tube for trapping methanol from out of the solvent that drips down through the reflux condensatio... | O=C(OC1CCCNC1)C(O)(c1ccccc1)c1ccccc1 | null | 40.1 | null |
553,947 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | N[C:2]1[CH:3]=[C:4]([CH3:21])[C:5]2[NH:6][C:7](=[O:20])[C:8]3[CH:18]=[C:17]([Br:19])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.C1C=CN=CC=1.[FH:28].N([O-])=O.[Na+].[OH-].[Na+]>>[Br:19][C:17]1[CH:16]=[N:15][C:9]2[N:10]([CH2:13][CH3:14])[C:11]3[N:12]=[C:2]([F:28])[CH:3]=[C:4]([CH3:21])[C:5]=3[NH:6][C:7]... | F | CCN1c2ncc(Br)cc2C(=O)Nc2c(C)cc(N)nc21 | null | O=N[O-] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 0 | 16 | A plastic bottle was charged with 2-amino-8-bromo-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (5.10 g, 14.6 mmol). HF-pyridine (100 g) was added and the resulting suspension was cooled to 0° C. Sodium nitrite (1.12 g, 16.1 mmol) was added in several portions over 30 min to produce a pur... | CCN1c2ncc(Br)cc2C(=O)Nc2c(C)cc(F)nc21 | null | 83.9 | null |
958,899 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH:1]1([C:7]2[O:8][C:9]([CH2:15][CH2:16][CH3:17])=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][O:19][CH2:20][CH2:21][N:22]([CH3:30])[C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][N:24]=1>>[CH3:18][O:19][CH2:20][CH2:21][N:22]([CH3:30])[C:23]1[N:24]=[CH:25][C:26]([NH:29][C:12]([C:10]2[... | CCCc1oc(C2CCCCC2)nc1C(=O)O | COCCN(C)c1ccc(N)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | With a procedure similar to example 16 above, 2-cyclohexyl-5-propyl-oxazole-4-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide was prepared from 2-cyclohexyl-5-propyl-oxazole-4-carboxylic acid and N2-(2-methoxy-ethyl)-N2-methyl-pyridine-2,5-diamine. LCMS calcd for C22H32N4O3 (m/e) 400, obsd 401 (... | CCCc1oc(C2CCCCC2)nc1C(=O)Nc1ccc(N(C)CCOC)nc1 | null | null | null |
21,873 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | [CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[C:11](Cl)([Cl:13])=[O:12]>C1C=CC=CC=1>[C:5]1([N:4]([CH:1]([CH3:3])[CH3:2])[C:11]([Cl:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1 | CC(C)Nc1ccccc1 | O=C(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of N-isopropylaniline (30 g) in dry benzene (150 ml) was cooled to 5°-10° C and phosgene passed therethrough slowly for 11/2 hours. The mixture was refluxed for 1 hour to remove excess phosgene, cooled and the amine hydrochloride was filtered off. The solvent was evaporated and the residue recrystallised fro... | CC(C)N(C(=O)Cl)c1ccccc1 | null | null | null |
126,291 | ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833 | null | 1985-01-01T00:01:00 | true | [CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[CH:6]=1.S(Cl)([Cl:16])(=O)=O>C(Cl)(Cl)Cl>[Cl:16][C:6]1[C:5]2[CH:7]=[C:8]([C:11]#[N:12])[CH:9]=[CH:10][C:4]=2[O:3][C:2]=1[CH3:1] | O=S(=O)(Cl)Cl | Cc1cc2cc(C#N)ccc2o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-methylbenzofuran-5-carbonitrile (J. Het. Chem., 4, 441, 1967) (1.52 g) and sulphuryl chloride (1.49 g) in chloroform (25 ml) was heated under reflux for 9 hours and then cooled. The solution was washed successively with water, dilute sodium hydroxide solution, water and then dried (Na2SO4). Evaporation ... | Cc1oc2ccc(C#N)cc2c1Cl | null | 24.3 | null |
1,174,447 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [Si]([O:8][CH2:9][CH2:10][N:11]([C:20]([C:22]1[CH:23]=[N:24][N:25]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][N:37]3[CH2:41][CH2:40][CH2:39][C@H:38]3[CH3:42])=[CH:29][CH:28]=2)[CH:26]=1)=[O:21])[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CC... | C[C@@H]1CCCN1CCCOc1ccc(-n2cc(C(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)OC(C)(C)C)cn2)cc1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of tert-butyl N-{2-(tert-butyldimethylsilyloxy)ethyl}-N-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}glycinate prepared in Example 67-(2) (0.220 g) in tetrahydrofuran (2.0 ml), a solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 M, 0.37 ml) was added and s... | C[C@@H]1CCCN1CCCOc1ccc(-n2cc(C(=O)N(CCO)CC(=O)OC(C)(C)C)cn2)cc1 | null | 101 | null |
1,638,500 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [ClH:1].[CH2:2]([C:7]1[N:8]=[C:9]([NH2:12])[NH:10][CH:11]=1)[CH2:3][CH2:4][C:5]#[CH:6].[N:13]([CH2:16][CH2:17][C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)=[N+:14]=[N-:15]>>[ClH:1].[S:20]1[CH:21]=[CH:22][C:18]([CH2:17][CH2:16][N:13]2[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][C:7]3[N:8]=[C:9]([NH2:12])[NH:10][CH:11]=3)[N:15]=[N:14]2)=... | [N-]=[N+]=NCCc1ccsc1 | C#CCCCc1c[nH]c(N)n1 | 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 | 4-Pent-4-ynyl-1H-imidazol-2-ylamine hydrochloride (0.090 g, 0.485 mmol) was reacted with 3-(2-Azido-ethyl)-thiophene (0.089 g, 0.581 mmol) following the general procedure for click reactions outlined above to produce 4-{3-[1-(2-Thiophen-3-yl-ethyl)-1H-[1,2,3]triazol-4-yl]-propyl}-1H-imidazol-2-ylamine hydrochloride (0.... | Nc1nc(CCCc2cn(CCc3ccsc3)nn2)c[nH]1 | null | 40.8 | null |
657,661 | ord_dataset-be508e976bbb4586a0cc3368302a62f8 | null | 2005-01-01T00:01:00 | true | [NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])=[O:4].[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[NH2:1][CH2:2][C:3]([NH:5]... | CC(C)(C)OC(=O)NCC(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | 1.5 | Boc-Gly-Gly-Phe-Gly-OH (200 mg) was dissolved in trifluoroacetic acid (4 ml) and stirred for 1.5 hours. The solvent was evaporated, and the residue was subjected to azeotropic distillations twice with methanol (10 ml) and twice with ethanol (10 ml) and washed with ether to obtain trifluoroacetic acid salt of Gly-Gly-Ph... | NCC(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCC(=O)O | null | null | null |
963,420 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:18][CH3:19])=[C:9]2[C:14](=O)[C:13]([CH3:17])([CH3:16])[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2]>C(Cl)Cl.C(OCC)C.[Zn+2].[I-].[I-]>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:18][CH3:19])=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:17])[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2] | CCOC(=O)c1sc(SC)c2c1CCC(C)(C)C2=O | null | null | [I-] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOCC | null | null | null | null | null | null | null | null | null | null | null | To a suspension of anhydrous ZnI2 (647 mg, 2.03 mmol) and Na(BH3CN) (117 mg, 1.86 mmol) in DCM (5 mL), a solution of 5,5-dimethyl-3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid ethyl ester (539 mg, 1.81 mmol) in DCM (5 mL) is added. The yellow suspension is refluxed over night before anot... | CCOC(=O)c1sc(SC)c2c1CCC(C)(C)C2 | null | null | null |
1,095,380 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | CON(C)[C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[CH:12]=2)[CH:10]=1)=[O:5].Br[C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][N:30]=1>>[CH3:24][O:23][C:20]1[N:19]=[C:18]([O:25][CH3:26])[C:17]([C:13]2[CH:12]=[C:11]([N:9]3[C... | Cc1ccnc(Br)c1 | COc1ncc(-c2cccc(-n3cnc(C(=O)N(C)OC)c3)c2)c(OC)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 | This compound is prepared by method C using compound 12m and 2-bromo-4-methylpyridine | COc1ncc(-c2cccc(-n3cnc(C(=O)c4cc(C)ccn4)c3)c2)c(OC)n1 | null | null | null |
1,219,291 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:20])[CH:15]1[CH2:19][CH2:18][NH:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH3:13][N:14]([CH3:20])[CH:15]1[CH2:19][CH2:18][N:17]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:16]1 | CCOC(=O)c1ccc(F)cc1 | CN(C)C1CCNC1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 130 | null | A mixture of ethyl 4-fluorobenzoate (4.47 g), dimethylpyrrolidin-3-ylamine (3.04 g), potassium carbonate (3.68 g) and dimethyl sulfoxide (20 ml) was heated at 130° C. for 7 hours. After cooling, the mixture was diluted with water and extracted with methyl tert-butyl ether. The organic phase was washed with water, dried... | CCOC(=O)c1ccc(N2CCC(N(C)C)C2)cc1 | null | null | null |
649,307 | ord_dataset-5d77a731aa10488794c824ad12021f57 | null | 2004-01-01T00:09:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH2:12]([N:14]([CH2:28][CH3:29])[CH2:15][CH2:16][NH:17][C:18]([C:20]1[CH:24]=[C:23]([CH3:25])[NH:22][C:21]=1[CH:26]=O)=[O:19])[CH3:13].N1CCCCC1>C(O)C>[CH2:28]([N:14]([CH2:12][CH3:13])[CH2:15][CH2:16][NH:17][C:18]([C:20]1[CH:24]=[C:23]([CH3:25... | CCN(CC)CCNC(=O)c1cc(C)[nH]c1C=O | O=C1Cc2cc(Br)ccc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCNCC1 | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of 5-bromo-2-oxindole (106 mg, 0.5 mmol), 2-formyl-5-methyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (126 mg, 1 equiv.) and piperidine (0.2 mL) in ethanol (2 mL) was heated in a sealed tube at 80° C. for 1 hr and then cooled. The precipitate was collected by vacuum filtration, washed with eth... | CCN(CC)CCNC(=O)c1cc(C)[nH]c1C=C1C(=O)Nc2ccc(Br)cc21 | null | null | null |
1,604,288 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH3:1][CH:2]([CH3:36])[CH2:3][CH:4]([C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[N:29]=[CH:28]2)=[CH:23][CH:22]=1)[O:5][C:6]1[CH:20]=[CH:19][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[O:11])=[CH:8][CH:7]=1.[OH-].[Li+]>CO>[CH3:1][CH:2]([CH3:36])[CH2:3][CH:4]([C:21]1[... | COC(=O)CCNC(=O)c1ccc(OC(CC(C)C)c2ccc(-n3cnc(C(F)(F)F)c3)cc2)cc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 1 | Methyl 3-(4-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenyl) butoxy)benzamido)propanoate (70 mg, 0.14 mmol) was dissolved in methanol (2 mL) and 1M lithium hydroxide (1 mL) was added. The reaction was stirred at room temperature for 1 hour. The methanol was removed under reduced pressure and the residue was... | CC(C)CC(Oc1ccc(C(=O)NCCC(=O)O)cc1)c1ccc(-n2cnc(C(F)(F)F)c2)cc1 | null | 77.5 | null |
883,552 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [CH2:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17]COC)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].Cl>C(O)C>[CH2:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3] | C=CCOc1ccc(C(=O)c2ccccc2OCOC)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 4-allyloxy-2′-(methoxymethyloxy)-benzophenone (1.1 g) in ethanol (15 mL) was concentrated hydrochloric acid (0.96 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and to the residue was added a saturated aqueous sodium hydroge... | C=CCOc1ccc(C(=O)c2ccccc2O)cc1 | null | 92.8 | null |
1,294,596 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [O:1]1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][NH:10][C:9]3=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[C:23]1[CH:33]=[CH:32][C:26]2[O:27][C:28]([F:31])([F:30])[O:29][C:25]=2[CH:24]=1>C1(C)C=CC=CC=1>[F:31][C:28]1([F:30])[O:27][C:26]2[CH:32]=[CH:33][C:23]([N:10]3[CH2:11][CH2:12][C:8]4(... | FC1(F)Oc2ccc(Br)cc2O1 | O=C1NCCC12CCC1(CC2)OCCO1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 110 | null | To a mixture of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (262 mg, 1.24 mmol, obtained in example 133, step 3), potassium carbonate (790 mg, 3.72 mmol) and cuprous iodide (354 mg, 1.86 mmol) was added a solution of 5-bromo-2,2-difluoro-benzo[1,3]dioxole (588 mg, 2.48 mmol) in 5 ml toluene under argon. The solut... | O=C1N(c2ccc3c(c2)OC(F)(F)O3)CCC12CCC1(CC2)OCCO1 | null | 76.8 | null |
21,102 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | [C:1]([NH:5][CH2:6][CH:7]([OH:25])[CH2:8][O:9][C:10]1[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[CH:19][C:11]=1[C:12]([CH2:14][CH2:15][C:16](O)=[O:17])=O)([CH3:4])([CH3:3])[CH3:2].O.[NH2:27][NH2:28]>>[C:1]([NH:5][CH2:6][CH:7]([OH:25])[CH2:8][O:9][C:10]1[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[CH:19][C:11]=1[C:12]1[CH2:14][C... | CNc1ccc(OCC(O)CNC(C)(C)C)c(C(=O)CCC(=O)O)c1 | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | By subjecting 3-[2-(3-t-butylamino-2-hydroxypropoxy)-5-(methylamino)benzoyl]propionic acid to cyclisation with hydrazine hydrate by a method similar to that described in Example 19(ix), the title compound may be prepared. | CNc1ccc(OCC(O)CNC(C)(C)C)c(C2=NNC(=O)CC2)c1 | null | null | null |
25,535 | ord_dataset-2ada3fda46fc44719ba0c8001f53c1b3 | null | 1977-01-01T00:06:00 | true | [N:1]([C:9]([N:12]=[C:13]=[O:14])([CH3:11])[CH3:10])=[N:2][C:3]([N:6]=[C:7]=[O:8])([CH3:5])[CH3:4].[C:15]1([NH:21][NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCC>[N:1]([C:9]([NH:12][C:13]([N:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:22])=[O:14])([CH3:10])[CH3:11])=[N:2][C:3]([NH:6][C:7]([N:21]([C:1... | NNc1ccccc1 | CC(C)(N=C=O)N=NC(C)(C)N=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCC | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a stirred solution of 4.0 grams (0.0204 moles) of 2,2'-azobis (2-isocyanato-propane) (from Example XXXIII) in 20 ml of pentane in a 50 ml erlenmeyer flask was added 4.42 grams (0.0408 moles) of phenylhydrazine and the reaction mixture stirred for 2 hours at room temperature. The solids that formed were filtered off,... | CC(C)(N=NC(C)(C)NC(=O)N(N)c1ccccc1)NC(=O)N(N)c1ccccc1 | null | null | null |
381,741 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.[CH2:9]([CH:11]1[O:13][CH2:12]1)Cl>>[CH2:9]([N:1]([CH2:9][CH:11]1[O:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1)[CH:11]1[O:13][CH2:12]1 | Cc1cccc(N)c1 | ClCC1CO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1 mole of N,N-bisglycidyl-m-toluidine was prepared from 4.8 moles of m-toluidine and 2 moles of epichlorohydrin. The excess m-toluidine was required to produce the oxirane ring and was filtered off as the hydrochloride after completion of the reaction. | Cc1cccc(N(CC2CO2)CC2CO2)c1 | null | 100 | null |
503,750 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | C[O:2][C:3]1[CH:11]=[CH:10][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1.[I-].[Li+].Cl>N1C(C)=CC(C)=CC=1C>[OH:2][C:3]1[CH:11]=[CH:10][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1 | COc1ccc2ccoc2c1 | null | null | Cl | [I-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1cc(C)nc(C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 6-methoxybenzofuran (16.9 g) in collidine (200 ml) was added lithium iodide (30.5 g), and the mixture was refluxed under argon atmosphere for 1 day and cooled. To the mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with 2N hydrochlo... | Oc1ccc2ccoc2c1 | null | 19 | null |
295,280 | ord_dataset-bb4579c57ddc48c6a01fad97dacb6293 | null | 1994-01-01T00:08:00 | true | Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[NH:20]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:21]1>>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:20]4[CH2:24][CH2:23][CH:22]([C:25]5[CH:26]... | c1cncc(C2CCNC2)c1 | O=C(O)c1cn(C2CC2)c2nc(Cl)c(F)cc2c1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (1.24 g, 4.4 mmol) and 3-(3-pyrrolidinyl)pyridine, a procedure analogous to that given in Example 1 provided the title compound (1.43 g, 82%) as a light beige solid, mp 226°-228° C. | O=C(O)c1cn(C2CC2)c2nc(N3CCC(c4cccnc4)C3)c(F)cc2c1=O | null | 82 | null |
1,561,799 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=[C:4]([Cl:12])[N:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+]>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C:13](=[O:15])[CH3:14])[CH:5]=[C:4]([Cl:12])[N:3]=1 | Nc1cc(Cl)nc(Cl)c1[N+](=O)[O-] | CC(=O)OC(C)=O | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | 2,6-Dichloro-3-nitropyridin-4-amine (208 mg, 1 mmol) was added to acetic anhydride (2 mL), and the reaction mixture was refluxed overnight. After cooled to room temperature, the reaction mixture was basified with aqueous Na2CO3 until the pH was 8. The resulting mixture was then extracted with CH2Cl2. The organic layer ... | CC(=O)Nc1cc(Cl)nc(Cl)c1[N+](=O)[O-] | null | null | null |
1,694,021 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1.[CH3:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](O)=[O:36]>>[NH2:1][C:2]1[N:7]=[CH:6][... | Cc1cccc(C(=O)O)c1 | COC(=O)CCCCS(C)(=O)=NC(=O)c1cnc(N)c(C#Cc2cccc(N)c2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In a manner similar to that described in Example 25, methyl 5-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate and 3-methylbenzoic acid were coupled to give the title compound as a white foam (82 mg). | COC(=O)CCCCS(C)(=O)=NC(=O)c1cnc(N)c(C#Cc2cccc(NC(=O)c3cccc(C)c3)c2)c1 | null | null | null |
1,092,114 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([O:12][C:13]1[C:14]2[O:22][CH:21]=[C:20]([C:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=3)[C:15]=2[CH:16]=[N:17][C:18]=1[NH2:19])[CH3:11].[CH2:29]([N:31]=[C:32]=[O:33])[CH3:30].CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:19][C:18]1[N:17]=[CH:16][C:15]2[C:20]([C:23]3[C... | C[C@@H](Oc1c(N)ncc2c(C3=CCNCC3)coc12)c1c(Cl)ccc(F)c1Cl | CCN=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 0.25 | A mixture of 7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydro-pyridin-4-yl)furo[3,2-c]pyridin-6-ylamine (10.0 mg, 0.0237 mmol), ethyl isocyanate (0.00310 g, 0.0436 mmol), DIPEA (0.033 mL, 0.19 mmol) in DMF (1 mL) was stirred at rt for 15 min. Purification by HPLC afforded the title compound as a colo... | CCNC(=O)N1CC=C(c2coc3c(O[C@H](C)c4c(Cl)ccc(F)c4Cl)c(N)ncc23)CC1 | null | null | null |
1,218,263 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:6]=[C:5]2[NH:19][C:20]1[N:24]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:23]2[CH:31]=[CH:32][C:33]([CH2:35][OH:36])=[CH:34][C:22]=2[N:21]=1.[CH3:37][O:38][CH2:39][C:40]1[CH:41]=[C:42](B(O)O)[... | C[Si](C)(C)CCOCn1nc(Nc2nc3cc(CO)ccc3n2C2CCCCC2)c2cc(Br)ccc21 | COCc1cccc(B(O)O)c1 | 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 | null | In a small microwave tube added (2-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-cyclohexyl-1H-benzo[d]imidazol-5-yl)methanol (52.4 mg, 0.0000918 mol), 3-(methoxymethyl)phenylboronic acid (25.1 mg, 0.000151 mol) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) complexed with dichl... | COCc1cccc(-c2ccc3c(c2)c(Nc2nc4cc(CO)ccc4n2C2CCCCC2)nn3COCC[Si](C)(C)C)c1 | null | 103.3 | null |
240,891 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | [CH3:1][O:2][CH2:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1Cl)=[CH:23][CH:22]=[CH:21][C:20]=2[O:27][CH3:28])(=[O:15])[CH2:12][CH2:13][CH3:14]>O1CCOCC1>[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1[NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[CH2:3][O:2][CH... | COCc1ccccc1N | CCCC(=O)c1cnc2c(OC)cccc2c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | 2-Methoxymethylaniline (1.0 g, 7.2 mmol) and 3-butyryl-4-chloro-8-methoxyquinoline (1.9 g, 7.2 mmol) were heated together under reflux in 1,4-dioxan (50 ml) for 2 hours. The solvent was evaporated and the residue dissolved in dichloromethane, washed with water, sodium hydrogen carbonate solution and brine, dried and ev... | CCCC(=O)c1cnc2c(OC)cccc2c1Nc1ccccc1COC | null | null | null |
1,295,503 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].[N+:12]([O-])([OH:14])=[O:13]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]=1[O:10][CH3:11])[C:5]#[N:6] | COc1ccc(C#N)cc1Br | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 2 | 3-bromo-4-methoxybenzonitrile (5.22 g, 24.62 mmol) was added to rapidly stirring fuming nitric acid (10 ml, 201 mmol) at 0° C. The ice bath was removed and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with ethyl acetate and water, and then the organic layer was washed w... | COc1c(Br)cc(C#N)cc1[N+](=O)[O-] | null | null | null |
1,018,038 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | Cl.[CH2:2]([O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][CH2:14][CH:15]2[C:20]([N:22]([CH2:31][C:32]1[CH:33]=[N:34][NH:35][CH:36]=1)[C:23]1[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)=[O:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N... | COc1ccc(N(Cc2cn[nH]c2)C(=O)C2CCCc3c(OCc4ccccc4)cccc32)cn1 | ClCCc1ccccn1 | 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 | By the reaction and treatment in the same manner as in Example 271 using 5-benzyloxy-N-[(pyrazol-4-yl)methyl]-N-(6-methoxypyridin-3-yl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide hydrochloride (0.70 g) and 2-(2-chloroethyl)pyridine (0.42 g) as starting materials, 5-benzyloxy-N-(6-methoxypyridin-3-yl)-N-({1-[2-(2-pyrid... | COc1ccc(N(Cc2cnn(CCc3ccccn3)c2)C(=O)C2CCCc3c(OCc4ccccc4)cccc32)cn1 | null | 56.6 | null |
1,035,604 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | Br[C:2]1[S:6][C:5]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[C:18]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])=[O:9])=[N:4][CH:3]=1.[SH:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1>>[CH:20]1([C:18]([C:12]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=2[NH:10][C:8]([NH:7][C:5]2... | Cc1ccc(NC(=O)Nc2ncc(Br)s2)c(C(=O)C2CCCC2)c1 | Sc1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1-(2-Cyclopentanecarbonyl-4-methyl-phenyl)-3-[5-(pyridin-4-ylsulfanyl)-thiazol-2-yl]-urea (110 mg, 25%) was prepared from 1-(5-bromo-thiazol-2-yl)-3-(2-cyclo pentanecarbonyl-4-methyl-phenyl)-urea (408 mg, 1 mmol) and 4-mercaptopyridine (222 mg, 2 mmol) following the general procedure Q. | Cc1ccc(NC(=O)Nc2ncc(Sc3ccncc3)s2)c(C(=O)C2CCCC2)c1 | null | 25.1 | null |
738,376 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.[I:16]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:6][C:7]=1[I:16] | O=C1OC(CO)CN1c1cccc(F)c1 | O=C1CCC(=O)N1I | 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 | null | null | null | null | null | null | null | null | null | null | null | 2 | A solution of alcohol 92 (10.74 g, 50.9 mmol) in trifluoroacetic acid (TFA, 50 mL) was treated with N-iodosuccinimide (12.03 g, 53.45 mmol, 1.05 equiv) at 25° C. and stirred for 2 h. When TLC and HPLC/MS showed the reaction was complete, the reaction mixture was concentrated in vacuo. The residue was then treated with ... | O=C1O[C@@H](CO)CN1c1ccc(I)c(F)c1 | null | 5.8 | null |
1,445,868 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([CH2:4][N:5]1[C:10](=[O:11])[C:9]2([CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12]2)[N:8](C(OC(C)(C)C)=O)[CH2:7][C@H:6]1[C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)(O)=[O:2].[NH2:33][C:34]1[CH:35]=[C:36]2[C:49](=[CH:50][CH:51]=1)[CH2:48][C@:38]1([C:46]3[C:41](=[N:42][CH:43]=[CH:44][CH:45]=3)[NH:40][... | CC(C)(C)OC(=O)N1C[C@@H](c2cc(F)cc(F)c2)N(CC(=O)O)C(=O)C12COCCOC2 | Nc1ccc2c(c1)C[C@@]1(C2)C(=O)Nc2ncccc21 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | 0.114 g (0.25 mmol) tert-butyl (R)-4-carboxymethyl-3-(3,5-difluoro-phenyl)-5-oxo-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate were stirred together with 67.9 mg (0.27 mmol) (R)-5-amino-1,3-dihydrospiro[inden-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, 63.3 mg (0.33 mmol) 1-ethyl-3-(3-dimethylaminopropyl)carbodiim... | O=C(CN1C(=O)C2(COCCOC2)NC[C@H]1c1cc(F)cc(F)c1)Nc1ccc2c(c1)C[C@@]1(C2)C(=O)Nc2ncccc21 | null | null | null |
1,481,976 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C(O[C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:19])=[CH:13][CH:12]=2)[C:7]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:5])C.Cl.[CH3:35][O:36][C:37](=[O:43])[C@@H:38]([NH2:42])[CH:39]([CH3:41])[CH3:40]>>[CH3:35][O:36][C... | CCOC(=O)c1onc(-c2ccc(NC(=O)Nc3ccc(F)cc3)cc2)c1-c1ccccc1 | COC(=O)[C@@H](N)C(C)C | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 3-{4-[3-(4-fluoro-phenyl)-ureido]-phenyl}-4-phenyl-isoxazole-5-carboxylic acid ethyl ester and (S)-2-amino-3-methyl-butyric acid methyl ester hydrochloride using the procedure as set forth in Example 5 and was obtained in 88.7% yield. Mass (ES+): 531 (M++1); 1H NMR (DMSO-d6) δ: 0.79... | COC(=O)[C@@H](NC(=O)c1onc(-c2ccc(NC(=O)Nc3ccc(F)cc3)cc2)c1-c1ccccc1)C(C)C | null | 88.7 | null |
690,517 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | [H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[Cl:22])[CH:14]=2)=[O:12])=[CH:5][CH:4]=1.[CH3:23]N(C=O)C>>[CH3:23][N:10]([CH2:9][C:6]1[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=1)[C:11]([C:13]1[S:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][C:19]=2[Cl:22])[CH:14]=1)=[O... | CN(C)C=O | O=C(NCc1ccncc1)c1cc2nccc(Cl)c2s1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | NaH (0.244 g, 6.09 mmol) was added to a solution of 7-chloro-thieno[3,2-b]pyridin-2-carboxylic acid (pyridin-4-ylmethyl)-amide (0.616 g, 2.03 mmol, prepared as described in Example 11) in DMF (10 mL). When the effervescence ceased, Mel (0.576 g, 4.06 mmol) was added dropwise. After 3 h the reaction mixture was quenched... | CN(Cc1ccncc1)C(=O)c1cc2nccc(Cl)c2s1 | null | 23 | null |
620,949 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | C(=O)([O-])[O-].[K+].[K+].[CH:7]1([NH2:10])[CH2:9][CH2:8]1.Br[CH:12]1[CH2:17][CH2:16][O:15][C:13]1=[O:14].O>C(#N)C>[CH:7]1([NH:10][CH:12]2[CH2:17][CH2:16][O:15][C:13]2=[O:14])[CH2:9][CH2:8]1 | NC1CC1 | O=C1OCCC1Br | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | 25 | 8 | After potassium carbonate (18.24 g, 132.0 mmol) was added to a solution of cyclopropylamine (5.50 ml, 80.0 mmol) and (±)-α-bromo-γ-butyrolactone (3.32 ml, 42.0 mmol) in acetonitrile (80 ml), the mixture was stirred at room temperature for 8 hours. To the reaction mixture, water was added and then this was extracted wit... | O=C1OCCC1NC1CC1 | null | 69.2 | null |
246,163 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | [CH2:1]([N:3]([CH2:15][CH3:16])[C:4]1[C:9]([F:10])=[CH:8][C:7]([N:11]=[C:12]=[S:13])=[C:6]([F:14])[CH:5]=1)[CH3:2].[CH3:17][NH:18][NH2:19]>C(O)C>[CH2:15]([N:3]([CH2:1][CH3:2])[C:4]1[C:9]([F:10])=[CH:8][C:7]([NH:11][C:12](=[S:13])[N:18]([CH3:17])[NH2:19])=[C:6]([F:14])[CH:5]=1)[CH3:16] | CCN(CC)c1cc(F)c(N=C=S)cc1F | CNN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Following procedures similar to those employed in Step A of Example 2, the reaction of 2.9 g (0.012 mole) of 4-diethylamino-2,5-difluorophenyl isothiocyanate with 0.55 g (0.012 mole) of methylhydrazine in 75 ml of ethanol yielded 3.4 g of 4-(4-diethylamino-2,5-difluorophenyl)-2-methyl-3-thiosemicarbazide. The nmr spect... | CCN(CC)c1cc(F)c(NC(=S)N(C)N)cc1F | null | 98.3 | null |
180,428 | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | null | 1988-01-01T00:11:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]1[C:15](=[O:16])[N:14]([CH3:17])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[S:11]1.[Br:22][CH2:23][CH2:24][CH2:25]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Br:22][CH2:23][CH2:24][CH2:25][O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C... | OCCCBr | COc1ccc(O)c(C2Sc3ccccc3N(C)C2=O)c1 | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of (-)-3,4-dihydro-2-(2-hydroxy-5-methoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine (6.3 g), which was prepared by the process (ii), in anhydrous tetrahydrofuran (70 ml), 3-bromo-1-propanol (8.8 g), triphenylphosphine (16.6 g) and then diethyl azodicarboxylate (10.0 ml) were added. The mixture was stirre... | COc1ccc(OCCCBr)c(C2Sc3ccccc3N(C)C2=O)c1 | null | 51 | null |
117,970 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | C([O:8][C:9]1[C:10]2[N:11]([CH:15]=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[ClH:19]>[Pd].C(O)C>[ClH:19].[OH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]2[CH:15]=[C:16]([CH3:18])[N:17]=[C:10]12 | Cc1cn2cccc(OCc3ccccc3)c2n1 | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 45 | A mixture of 8-benzyloxy-2-methyl-imidazo[1,2-a]pyridine (5.9 g), 6.1 N HCl(4.2 ml), 10% Palladium-on-charcoal (5.9 g) and 240 ml ethanol was hydrogenated under a H2 -pressure of about 3.5 kg/cm2 for 22 hrs. at room temperature, after which period a further 2 g of fresh catalyst was added and hydrogenation continued fo... | Cc1cn2c(n1)C(O)CCC2 | null | null | null |
186,336 | ord_dataset-754e10d30fb249229e130865010ab25b | null | 1989-01-01T00:03:00 | true | [O:1]=[C:2]1[CH2:8][CH2:7][S:6][CH2:5][CH:4]([C:9]([OH:11])=O)[NH:3]1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=2)=[CH:15][CH:14]=1>CN(C)C=O>[O:1]=[C:2]1[CH2:8][CH2:7][S:6][CH2:5][CH:4]([C:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]([CH3:26])[CH2:21][C:2... | O=C1CCSCC(C(=O)O)N1 | CC1CC(=O)NN=C1c1ccc(N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | 5.3 g (0.03 mole) of 5-oxo-perhydro-(1,4)-thiazepine-3-carboxylic acid and 6.1 g (0.03 mole) of N,N'-carbonyl-diimidazole are stirred in 15 ml of dimethylformamide at 50° c. for 15 minutes. After addition of 4.9 g (0.03 mole) of 6-(4-amino-phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone, the mixture is stirred at room ... | CC1CC(=O)NN=C1c1ccc(NC(=O)C2CSCCC(=O)N2)cc1 | null | null | null |
828,423 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[NH:15][C:16](=[O:20])/[CH:17]=N/O)([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:22]>>[C:11]([C:9]1[CH:8]=[C:7]2[C:6](=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)[NH:15][C:16](=[O:20])[C:17]2=[O:22])([CH3:14])([CH3:13])[CH3:12] | CC(C)(C)c1ccc(NC(=O)/C=N/O)c(C(C)(C)C)c1 | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | null | N-(2,4-Di-tert-butyl-phenyl)-2-[(E)-hydroxyimino]-acetamide (500 mg, 1.7 mmol) in concentrated sulfuric acid (3.8 mL) was heated at 90° C. for 2 h. This solution was cooled at 0° C. and slowly added to ice-water (15 mL), the brown precipitate was filtered off and purified by chromathography on silica gel with a gradien... | CC(C)(C)c1cc2c(c(C(C)(C)C)c1)NC(=O)C2=O | null | 42 | null |
1,476,866 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH:1]1([C:4]2[CH:5]=[CH:6][C:7](/[C:12](/[C:20]3[CH:21]=[CH:22][C:23]4[O:27][CH2:26][CH2:25][C:24]=4[CH:28]=3)=[CH:13]/[C@@H:14]3[NH:18][C:17](=[O:19])[CH2:16][CH2:15]3)=[N:8][C:9]=2[O:10][CH3:11])[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:12]([C:20]3[CH:21]=[CH:22][C:23]4[O:27][CH2:26][CH2:25... | [H][H] | COc1nc(/C(=C/[C@H]2CCC(=O)N2)c2ccc3c(c2)CCO3)ccc1C1CC1 | 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 | 10% palladium-activated carbon (50 mg) was added to a solution of (5R)-5-[(E)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-(2,3-dihydro-1-benzofuran-5-yl)ethenyl]pyrrolidin-2-one (240 mg) in methanol (3 mL), and the mixture was stirred at room temperature for four hours in a hydrogen atmosphere. The reaction solution was ... | COc1nc(C(C[C@H]2CCC(=O)N2)c2ccc3c(c2)CCO3)ccc1C1CC1 | null | null | null |
818,178 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[CH2:9]([C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)[CH3:10].[K+].[Br-]>>[CH2:9]([C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:1]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[NH:2])=[CH:13][CH:12]=1)[CH3:10] | CCc1ccc(N)cc1 | N#Cc1cccnc1 | null | [Br-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 3-cyanopyridine (8.5 g, 83 mmol) and 4-ethylaniline (10 g, 83 mmol) by following the procedure described in preparation 10 (15.8 g, yield 84.9%, mp 134-136 C, purity 99.8% by HPLC). 1H-NMR (CDCl3):δ 1.22-1.26 (t, 3H), 2.60-2.65 (q, 2H), 5.09 (bs, 2H, D2O exchangeable), 6.88-6.89 (d,... | CCc1ccc(NC(=N)c2cccnc2)cc1 | null | 84.9 | null |
1,499,696 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12].S(Cl)(Cl)=O.[CH3:18]O>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([O:13][CH3:18])=[O:12] | CO | O=C(O)c1ccc2ccccc2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0 | null | To an ice-cooled solution of quinoline-2-carboxylic acid 3.1 (10 g, 0.0578 mol) in 100 mL of absolute methanol was added dropwise thionyl chloride (20 g, 0.173 mol). After the addition was completed, the mixture was heated to reflux for 2 h. The solvent was then evaporated to dryness under reduced pressure and treated ... | COC(=O)c1ccc2ccccc2n1 | null | null | null |
536,121 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([N:11]=[C:12]2[S:16][CH2:15][C:14]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[NH:13]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:21](Br)[CH:22]([CH3:24])[CH3:23]>>[CH2:21]([N:13]1[C:14]2([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][S:16][C:12]1=[N:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=... | Cc1cc(N=C2NC3(CCCC3)CS2)ccc1[N+](=O)[O-] | CC(C)CBr | null | null | null | null | null | null | null | 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-Methyl-4-nitroaniline was converted to 3-methyl-4-nitrophenyl isothiocyanate according to Method A2a, Step 3. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7a to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. ... | Cc1cc(N=C2SCC3(CCCC3)N2CC(C)C)ccc1[N+](=O)[O-] | null | null | null |
1,181,525 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | F[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(C)(C)C.[K+]>CS(C)=O>[CH2:12]([C:19]1[CH:20]=[CH:21][C:22]([NH:23][C:2]2[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][CH:5]=[CH:6][C:7]=2[C... | Cc1cccc([N+](=O)[O-])c1F | Nc1ccc(Cc2ccccc2)cc1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | The product (1.01 g) is obtained according to the method of stage 1 of Example 4, by using 1.13 g of 2-fluoro-3-methyl-nitrobenzene and 2 g of 4-benzyl-aniline in the presence of 1.31 g of potassium tert-butanolate in 30 mL of DMSO. | Cc1cccc([N+](=O)[O-])c1Nc1ccc(Cc2ccccc2)cc1 | null | null | null |
1,676,713 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]1([C:7]2[CH:17]=[N:16][C:10]3[O:11][CH2:12][C:13](=[O:15])[NH:14][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:18][C:17]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][C:9]2[NH:14][C:13](=[O:15])[CH2:12][O:11][C:10]=2[N:16]=1 | O=C1CCC(=O)N1Br | O=C1COc2ncc(-c3ccccc3)cc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 80 | null | In a 10 ml microwave vial was 7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (50 mg, 0.221 mmol) and N-bromosuccinimide (78.6 mg, 0.441 mmol) in dimethylformamide (1 ml). The reaction mixture was heated to 80° C. under microwave irradiation for 30 minutes. The reaction mixture was cooled to room temperature and diluted... | O=C1COc2nc(Br)c(-c3ccccc3)cc2N1 | null | 90.5 | null |
9,822 | ord_dataset-53cd7fd33c6f4f1c804e187bec94be57 | null | 1976-01-01T00:07:00 | true | C(C1[C:12]2[C:7](=[CH:8][C:9]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[C:10]([Cl:13])[CH:11]=2)[C:6](=[O:20])[CH2:5][CH2:4]1)#N.[C:21]([OH:24])(=[O:23])[CH3:22].S(=O)(=O)(O)O>O>[O:20]=[C:6]1[C:7]2[C:12](=[CH:11][C:10]([Cl:13])=[C:9]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:8]=2)[CH:22]([C:21]([O... | CC(=O)O | N#CC1CCC(=O)c2cc(C3CCCCC3)c(Cl)cc21 | 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 | null | null | A mixture of 19 g of 4-cyano-6-chloro-7-cyclohexyl-3,4-dihydro-naphthalene-1(2H)-one, 36 ml of glacial acetic acid, 43 ml of concentrated sulfuric acid, and 29 ml of water is refluxed overnight. It is then poured into water, and the aqueous mixture is extracted with ethyl acetate. After drying and evaporation of the so... | O=C1CCC(C(=O)O)c2cc(Cl)c(C3CCCCC3)cc21 | null | null | null |
153,446 | ord_dataset-128a4f3f44e844218b1c319ab4de3893 | null | 1987-01-01T00:02:00 | true | [CH3:1][C:2]1[O:3][C:4]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[C:5]([CH2:7][C:8]([O:10]CC)=[O:9])[N:6]=1.CO.[OH-].[K+]>O>[CH3:1][C:2]1[O:3][C:4]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:6]=1 | CCOC(=O)Cc1nc(C)oc1-c1ccco1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | null | 1.1 g of ethyl 2-[2-methyl-5-(2-furyl)-4-oxazolyl]acetate, 20 ml of methanol, 5 ml of water and 0.7 g of potassium hydroxide are treated in the same manner as described in Example 16. 0.55 g of 2-[2-methyl-5-(2-furyl)-4-oxazolyl]acetic acid is obtained. Yield: 56.5% | Cc1nc(CC(=O)O)c(-c2ccco2)o1 | null | 56.8 | null |
1,005,512 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[C:4]([C:13]2[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:15][CH:14]=2)=[N:3]1.N([CH2:33][C:34](C)([OH:36])[CH3:35])N>>[CH3:33][C:34]([OH:36])([CH3:35])[CH2:1][N:2]1[CH:6]=[C:5]... | Cn1cc(-c2ccncc2)c(-c2ccc(OCc3ccc4ccccc4n3)cc2)n1 | CC(C)(O)CNN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure for the preparation of 2-[4-(1-Methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline but substituting 1-Hydrazino-2-methyl-propan-2-ol provided the title compound. 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=6.2 Hz, 2H), 8.19 (d, J=8.7 Hz, 1H), 8.07 (d, J=8.7 Hz, 1H), 7.82 (d, J=7.9 Hz, 1H), ... | CC(C)(O)Cn1cc(-c2ccncc2)c(-c2ccc(OCc3ccc4ccccc4n3)cc2)n1 | null | null | null |
1,339,852 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[Cl:15].[Cl:16][C:17]1[N:18]=[C:19]([C:24](O)=[O:25])[NH:20][C:21]=1[CH2:22][CH3:23].O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>>[Cl:15][C@H:3]1[C@@H:2]([NH:1][C:24]([C:19]2[NH:20][C:21]([CH2:22][CH3:23])=[C... | CCc1[nH]c(C(=O)O)nc1Cl | CC(C)(C)OC(=O)N1CC[C@H](N)[C@H](Cl)C1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | O | null | null | null | null | null | null | null | null | null | null | null | The same operation as in Example (196b) was performed using tert-butyl cis(±)-4-amino-3-chloropiperidine-1-carboxylate obtained in Example (198a) (134 mg, 0.571 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (99.7 mg, 0.571 mmol), 1-hydroxybenzotriazole hydrate (116 mg, 0.856 mmol), WSC... | CCc1[nH]c(C(=O)N[C@H]2CCN(C(=O)OC(C)(C)C)C[C@H]2Cl)nc1Cl | null | 73.4 | null |
1,720,371 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][N:19]3S(C3C=CC(C)=CC=3)(=O)=O)=[C:15]([C:32]3[O:33][C:34]([CH2:37][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1.[OH-].[Na+]>C(O)(C)C.O>[Cl:1][C:2]1[C:7]([NH:8][S:9](... | Cc1ccc(S(=O)(=O)n2ncc3c(-c4nnc(CN5CCOCC5)o4)cc(-c4cnc(Cl)c(NS(C)(=O)=O)c4)cc32)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | O | null | null | null | null | null | null | null | null | null | 25 | 8 | N-(2-Chloro-5-{1-[(4-methylphenyl)sulfonyl]-4-[5-(4-morpholinylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide (52 mg, 0.081 mmol) was placed in isopropanol (3 ml) and 2M sodium hydroxide (1 ml, 2.0 mmol) added. The mixture was stirred at room temperature overnight and blown to dryness und... | CS(=O)(=O)Nc1cc(-c2cc(-c3nnc(CN4CCOCC4)o3)c3cn[nH]c3c2)cnc1Cl | null | 20.2 | null |
1,266,044 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[NH:5][C:4]=2[N:3]=1.I[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:17][CH2:18][CH3:19])[C:4]=2[N:3]=1 | CCCI | C=CCn1c(Cl)nc2[nH]c(=O)[nH]c(=O)c21 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 50 | null | A mixture of 8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.5 g, 6.6 mmol), 1-iodopropane (1.2 g, 6.9 mmol) and sodium carbonate (0.9 g, 8.5 mmol) in DMF (40 ml) was heated at 50° C. for 18 hours. The reaction mixture was concentrated in vacuo and the residue treated with water (60 ml) and extracted with... | C=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2CCC | null | 46.2 | null |
1,131,723 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=2[Cl:19])[C:5]([NH2:8])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][C:31]([NH:34][S:35]([CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])(=[O:37])=[O:36])=[CH:30][CH:29]=2)O1>>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:2... | CCN(CC)CCS(=O)(=O)Nc1ccc(B2OC(C)(C)C(C)(C)O2)cc1 | Nc1ncc(Br)cc1OCc1c(F)ccc(F)c1Cl | null | null | null | null | null | null | null | 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-diethylamino-ethanesulfonic acid {4-[6-amino-5-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-3-yl]-phenyl}-amide was prepared following the general Suzuki coupling procedure 3 from 5-bromo-3-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-2-ylamine and 2-diethylamino-ethanesulfonic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaboro... | CCN(CC)CCS(=O)(=O)Nc1ccc(-c2cnc(N)c(OCc3c(F)ccc(F)c3Cl)c2)cc1 | null | 60 | null |
1,559,932 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:3]1.[C:16]([CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[C:21](O)=[O:22])#[N:17]>>[C:16]([CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([N:7]1[CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=... | CC1CN(c2ccc(C#N)cn2)CCN1 | CC(C)(CCC#N)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was synthesized from 6-(3-methylpiperazin-1-yl)nicotinonitrile and 4-cyano-2,2-dimethylbutanoic acid as described for example 37 step 3 (400 mg, yield 17%) as yellow viscous liquid. 1H NMR (300 MHz, MeOD) δ 8.40-8.39 (dd, J=2.2 Hz, 0.7 Hz, 1H), 7.76-7.72 (dd, J=9.1 Hz, 2.3 Hz, 1H), 6.86-6.83 (d, J=9.0 Hz,... | CC1CN(c2ccc(C#N)cn2)CCN1C(=O)C(C)(C)CCC#N | null | 17 | null |
1,386,333 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([CH:18]=NO)=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([SiH](CC)CC)C.C(=O)([O-])[O-:36].[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:... | Cc1cc(C2=NOC(c3cc(Cl)cc(Cl)c3)(C(F)(F)F)C2)ccc1C=NO | O=C([O-])[O-] | null | CC[SiH](CC)CC | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 65 | null | A mixture of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde oxime (14.20 g, 31.34 mmol), triethyl silane (10.3 mL, 7.53 g, 62.8 mmol), sodium carbonate (5.43 g, 39.3 mmol), palladium bis(diphenylphosphine)-ferrocene dichloride CH2Cl2-complex (1.28 g, 1.57 mmol) and DMF (25... | Cc1cc(C2=NOC(c3cc(Cl)cc(Cl)c3)(C(F)(F)F)C2)ccc1C=O | null | 76.2 | null |
154,939 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | C1([N:7]=C=NC2CCCCC2)CCCCC1.C([O:19][CH:20]1[CH2:24][CH2:23][N:22]([CH2:25][C:26](O)=[O:27])[C:21]1=[O:29])(=O)C.ON1C(=O)CCC1=O>C(Cl)(Cl)Cl>[OH:19][CH:20]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([NH2:7])=[O:27])[C:21]1=[O:29] | CC(=O)OC1CCN(CC(=O)O)C1=O | C(=NC1CCCCC1)=NC1CCCCC1 | null | O=C1CCC(=O)N1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 4 | 1.64 g of dicyclohexylcarbodiimide dissolved in 20 ml of chloroform are added at room temperature to 1.5 g of (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid, 40 ml of chloroform and 0.86 g of N-hydroxysuccinimide. After 4 hours, the solid is filtered, whereupon the filtrate is concentrated and again filtered. The ... | NC(=O)CN1CCC(O)C1=O | null | null | null |
646,519 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[CH:13]1([CH2:19][C@H:20]([N:24]2[C:28](=[O:29])[C@H:27]([CH2:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[NH:26][C:25]2=[O:37])[C:21](O)=[O:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][C:5]1... | O=C(O)[C@H](CC1CCCCC1)N1C(=O)N[C@@H](CC2CCCCC2)C1=O | CCOC(=O)Cc1csc(N)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 | By using the conditions described in Step (iv) of Example 17, ethyl 2-amino-4-thiazoleacetate was condensed with (S,S)-3-cyclohexyl-2-[4-(cyclohexyl)methyl-2,5-dioxoimidazolidinyl]propanoic acid [Example 17, Step (iii)] to give the title compound as a colorless foam: EI-HRMS m/e calcd. for C26H38N4O5S (M+) 519.2641, fo... | CCOC(=O)Cc1csc(NC(=O)[C@H](CC2CCCCC2)N2C(=O)N[C@@H](CC3CCCCC3)C2=O)n1 | null | null | null |
1,574,403 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Br[C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:30][C:31]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=C... | COc1ccc(N(C)C(=O)[C@H](Cc2cccc(Br)c2)NC(=O)OC(C)(C)C)cc1 | C=CB1OC(C)(C)C(C)(C)O1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | null | null | A suspension of (S)-tert-butyl 3-(3-bromophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (6.3 g, 13.6 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (3.3 g, 20.4 mmol), potassium carbonate (54 ml, 0.4 M) and tetrakis(triphenylphosphine)palladium(0) (0.79 g, 0.68 mmol) in 50 ml of DME, was h... | C=Cc1cccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)N(C)c2ccc(OC)cc2)c1 | null | 98 | null |
541,371 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:7][C:6]=2[CH:5]=[C:4]([Cl:18])[CH:3]=1.[CH2:19]([OH:22])[C:20]#[CH:21]>C1(C)C=CC=CC=1.C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[Cl:18][C:4]1[CH:3]=[C:2]([C:21]#[C:20][CH2:19... | C#CCO | Clc1cc(Br)c2oc(-c3ccccc3Cl)nc2c1 | null | Cl[Pd]Cl | [Cu]I | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 6 | A solution of 17.15 g (50 mmol) of 7-bromo-5-chloro-2-(2-chlorophenyl)-benzoxazole and 4.40 ml (75 mmol) of propargylalcohol in 32 ml of toluene and 64 ml of triethylamine was heated under nitrogen to 80-5° C. with 175.4 mg (250 μM) of bis(triphenylphosphine)palladium (II) chloride and 8.6 mg (4.5 μM) of copper (1) iod... | OCC#Cc1cc(Cl)cc2nc(-c3ccccc3Cl)oc12 | null | 85.7 | null |
643,814 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[N:23]3[C:19]([S:20][CH:21]=[CH:22]3)=[N:18][C:17]=2[Cl:24])(=[O:15])=[O:14])[CH:5]=1.[CH3:25][NH2:26]>C1COCC1>[Cl:24][C:17]1[N:18]=[C:19]2[N:23]([C:16]=1[S:13]([N:6]1[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([CH2:3][CH2:2][NH... | O=S(=O)(c1c(Cl)nc2sccn12)n1cc(CCBr)c2ccccc21 | CN | 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 | 50 | null | A solution of 3-(2-bromoethyl)-1-(6-chloroimidazo[2,1-b]thiazole-5-sulfonyl)indole (92 mg, 0.20 mmol) in THF is treated with methyl amine (2M in methanol, 0.4 mL, 2 eq.), heated at 50° C. for 24 h, cooled and concentrated in vacuo. The resultant residue is purified by HPLC1 to give the title product as a white solid, 1... | CNCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12 | null | null | null |
345,036 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | [OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]3=[O:22])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>C(Cl)Cl.N1C=CC=CC=1>[CH3:21][O:20][CH2:19][CH:17]1[O:16][C:15](=[O:22])[N:14]([C:11]2[C... | O=C(Cl)c1ccccc1 | COCC1CN(c2ccc([C@H]3CC[C@H](O)CC3)cc2)C(=O)O1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 3 | A solution of 0.5 g (1.639 mmol) of (RS)-3-[4-(trans-4-hydroxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one in 20 ml of methylene chloride and 5 ml of pyridine was treated dropwise with a solution of 0.95 ml (8.195 mmol) of benzoyl chloride in 10 ml of methylene chloride and stirred at room temperature for a fu... | COCC1CN(c2ccc([C@H]3CC[C@H](OC(=O)c4ccccc4)CC3)cc2)C(=O)O1 | null | null | null |
563,063 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | [N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:14][C@H:15]([OH:31])[C@@H:16]([NH:24]C(=O)C(F)(F)F)[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:8][CH:7]=2)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[N:1]1[N:2]=[CH:3][N:4]([C... | CC(C)(C)OC(=O)NN(Cc1ccc(-n2cnnc2)cc1)C[C@H](O)[C@H](Cc1ccccc1)NC(=O)C(F)(F)F | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 0.756 g (1.38 mmol) of 1-[p-(1,2,4-triazol-4-yl)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)-(trifluoroacetyl)amino-6-phenyl-2-azahexane (Example 14d) is initially introduced in 28 ml of methanol, and 6.9 ml (6.89 mmol) of a 1 M aqueous solution of potassium carbonate are then added. The reaction mixture is... | CC(C)(C)OC(=O)NN(Cc1ccc(-n2cnnc2)cc1)C[C@H](O)[C@@H](N)Cc1ccccc1 | null | null | null |
1,488,195 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:18][CH:19]([C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)[CH3:20])=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:27][CH3:28])=[C:5]([CH3:29])[O:4][N:3]=1.[CH2:30]([N:32]=[C:33]=S)[CH3:31]>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:27][CH3:28])=[CH:9][C:10]3[C:1... | COc1cc2c(NC(C)c3cnn(C)c3)c(N)cnc2cc1-c1c(C)noc1C | CCN=C=S | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 60 | null | 7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N4-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)quinoline-3,4-diamine (70 mg, 0.178 mmol, for a preparation see intermediate 22) was dissolved in ethanol (5 ml) and ethylisothiocyanate (31.1 mg, 0.357 mmol) was added. The solution was heated at 60° C. for 3 h, then cooled and evaporated in... | CCNc1nc2cnc3cc(-c4c(C)noc4C)c(OC)cc3c2n1C(C)c1cnn(C)c1 | null | 40.3 | null |
870,507 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C@@H:14]([CH3:31])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:39][CH2:40][CH2:41][N:42]1[CH:46]=[CH:45][CH:44]=... | BrCCCn1cccc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 70 | 3 | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (75 mg, 0.17 mmol) was dissolved in DMF (1 mL) at room temperature. K2CO3 (47 mg, 0.34 mmol) was added followed by 1-(3-bromopropyl)-pyrrole and the reaction was allowed to stir at 70° C. for 3 hrs. The reaction mi... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cccc3)cc2)c2ccccc21 | null | null | null |
538,163 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[C:31]([Cl:36])[CH:32]=4)[CH:27]=3)(=[O:25])=[O:24])[CH2:19][CH:18]2[C:37]([O:39]CC)=[O:38])=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C... | CCOC(=O)C1CN(S(=O)(=O)c2ccc3cc(Cl)ccc3c2)CCN1C(=O)[C@H]1CC[C@H](NC(=O)OC(C)(C)C)CC1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 15 | To a solution of ethyl 1-(trans-4-tert-butoxycarbonylaminocyclohexane-1-ylcarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinecarboxylate (740 mg) in ethanol (15 ml) was added 1 N sodium hydroxide solution (10 ml), and the solution was stirred at room temperature for 15 hours. The reaction solution was concentrate... | CC(C)(C)OC(=O)N[C@H]1CC[C@H](C(=O)N2CCN(S(=O)(=O)c3ccc4cc(Cl)ccc4c3)CC2C(=O)O)CC1 | null | null | null |
1,318,538 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | C(OC([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31](=[O:43])[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=3)[CH:26]=[CH:25]4)[N:18]=[CH:17][N:16]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:42... | CC(C)(C)OC(=O)N1CCC(NCc2cc(Oc3ccc4c(ccn4C(=O)Nc4cccc(C(F)(F)F)c4)c3)ncn2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | (±)-3-({6-[1-(3-Trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester (20 mg, 3.30 mmol) is stirred in a solution of DCM (2 mL) and TFA (0.5 mL) overnight. After removal of solvents, the residue is quenched with saturated aqueous sodium bicarbonat... | O=C(Nc1cccc(C(F)(F)F)c1)n1ccc2cc(Oc3cc(CNC4CCNC4)ncn3)ccc21 | null | null | null |
998,459 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[CH3:30][N:31]([CH3:42])[CH2:32][CH2:33][O:34][C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38]>CC(O)C.Cl.C(C... | CN(C)CCOc1cccc(N)c1 | O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Cl)n2)c1)C(F)(F)F | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | ClCCl | null | null | null | null | null | null | null | null | null | 80 | 8 | To a suspension of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (150 mg, 0.36 mmol) (see Example 1, Step C) in i-PrOH (4 mL) were added 3-{[2-(dimethylamino)ethyl]oxy}aniline (80 mg, 0.45 mmol) and 12 N HCl (3 drops). The reaction was stirred overnight at 80° C. The crude... | CN(C)CCOc1cccc(Nc2nccc(-c3c(-c4cccc(NC(=O)C(F)(F)F)c4)nn4ccccc34)n2)c1 | null | 84 | null |
464,995 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | [CH:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([O:12][CH3:13])=[O:11])=[O:2].CS(O[CH2:19][CH:20]=[CH:21][C:22]([F:25])([F:24])[F:23])(=O)=O>>[CH:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]([CH2:19][CH:20]=[CH:21][C:22]([F:25])([F:24])[F:23])[C:4]=1[C:10]([O:12][CH3:13])=[O:11])=[O:2] | COC(=O)c1[nH]c(C)c(C)c1C=O | CS(=O)(=O)OCC=CC(F)(F)F | null | null | null | null | null | null | null | 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 (trans) was prepared as a pale yellow oil in 60.0% yeild in a similar procedure to that described in Referential Example 9 by using methyl 3-formyl-4,5-dimethylpyrrole-2-carboxylate and 4,4,4-trifluoro-2-butenyl methanesulfonate (trans). | COC(=O)c1c(C=O)c(C)c(C)n1CC=CC(F)(F)F | null | null | null |
711,982 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([CH3:15])=[O:14])=[O:5].[I:20]N1C(C)(C)C(=O)N(I)C1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C(=O)C>[I:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:2]([CH3:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1... | CC1(C)C(=O)N(I)C(=O)N1I | Cc1ccccc1C(=O)Nc1ccccc1S(C)=O | null | [Pd+2] | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 90 | 2 | Into the same reactor as in Example 1 were charged 0.10 g of palladium acetate, 0.40 g of 2-methyl-2′-methylsulfinylbenzanilide, 0.33 g of 1,3-diiodo-5,5-dimethylhydantoin and 5 ml of N,N-dimethylacetamide. The mixture thus obtained was stirred at 90° C. for 2 hours. After cooling to room temperature, the reaction mixt... | Cc1cccc(I)c1C(=O)Nc1ccccc1S(C)=O | null | 124 | null |
93,566 | ord_dataset-f0d0fe3f599c471ca1c011dbbcdeeff2 | null | 1982-01-01T00:04:00 | true | [F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:16])=[C:11]([CH3:15])[C:12]=2[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]1.[OH-].[Na+]>C(O)C>[F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:16])=[C:11]([CH3:15])[C:12]=2[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]1 | CCOC(=O)c1cn(CCF)c2c(F)c(C)c(F)cc2c1=O | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 3 | 3.13 g of ethyl 1-(2-fluoroethyl)-6,8-difluoro-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate are suspended in 50 ml of ethanol, and 50 ml of an aqueous 2% sodium hydroxide solution are added thereto. The suspension is stirred at room temperature for 3 hours. Then, the reaction mixture is evaporated under reduced pr... | Cc1c(F)cc2c(=O)c(C(=O)O)cn(CCF)c2c1F | null | 100 | null |
1,496,842 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [N:1]1([C:7]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([C:19]3[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:23][... | Nc1ccc(-c2nc(N3CCOCC3)nc(N3CCOCC3)n2)cc1 | O=C=Nc1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline (0.140 g 0.40 mmoles) and 4-chlorophenyl isocyanate (94 mg, 0.61 mmoles), the title compound was isolated as a white solid. Yield; 60 mg (30%); (M+H)=496.3 | O=C(Nc1ccc(Cl)cc1)Nc1ccc(-c2nc(N3CCOCC3)nc(N3CCOCC3)n2)cc1 | null | null | null |
837,427 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[O:5][CH:6]([CH2:20][CH3:21])[C:7]([NH:9][C:10]([CH3:19])([CH3:18])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][S:16][CH3:17])=[O:8].I([O-])(=O)(=O)=[O:27].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[O:5][CH:6]([CH2:20][CH3:21])[C:7]([NH:9]... | CCC(Oc1cc(Cl)cc(Cl)c1)C(=O)NC(C)(C)C#CCCCSC | [O-][I+3]([O-])([O-])[O-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | 2.5 | To a stirred solution of 2-(3,5-dichlorophenoxy)-N-(6-methyl-1-methylthio-hept-4-yn-6-yl) butyramide (0.21 g) in ethanol (2.5 ml) at ambient temperature was added dropwise a solution of sodium periodate (0.13 g) in water (2.5 ml). The mixture was stirred for 2.5 hours, stored for 18 hours then evaporated under reduced ... | CCC(Oc1cc(Cl)cc(Cl)c1)C(=O)NC(C)(C)C#CCCCS(C)=O | null | null | null |
67,119 | ord_dataset-b5f1497361c94e5fa55257200189a6a4 | null | 1980-01-01T00:06:00 | true | [C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][N:13]([CH:15]([C:30]([O:32][CH3:33])=[O:31])[C:16]3[CH:21]=[CH:20][C:19]([O:22]CC4C=CC=CC=4)=[CH:18][CH:17]=3)[C:12]2=[O:34])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][N:13]([CH:15]([C:30]([O:32][CH3:33])=[O:31])[C:... | [H][H] | COC(=O)C(c1ccc(OCc2ccccc2)cc1)N1CC(NC(=O)Cc2ccccc2)C1=O | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 3-(2-Phenylacetamido)-1-(α-methoxycarbonyl-4-benzyloxybenzyl)-2-azetidinone (70 mg) was dissolved in absolute ethanol (10 ml), and to the solution, there was added 10% palladium on carbon (30 mg). The mixture was subjected to catalytic reduction in a stream of hydrogen gas at ordinary temperature and ordinary atmospher... | COC(=O)C(c1ccc(O)cc1)N1CC(NC(=O)Cc2ccccc2)C1=O | null | 71.1 | null |
1,182,371 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [C:1]([O:5][C:6]([NH:8][C@:9]1([CH3:24])[C@H:13]([CH2:14][F:15])[CH2:12][N:11]([C@@H](C2C=CC=CC=2)C)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd].[H][H]>[C:1]([O:5][C:6]([NH:8][C@:9]1([CH3:24])[C@H:13]([CH2:14][F:15])[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2] | C[C@H](c1ccccc1)N1C[C@@H](CF)[C@@](C)(NC(=O)OC(C)(C)C)C1 | [H][H] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of (3R,4R)-3-(tert-butoxycarbonylamino)-4-fluoromethyl-3-methyl-1-[(1R)-1-phenylethyl]pyrrolidine (250 mg, 0.743 mmol) in ethanol (10 mL) was added 10% palladium-carbon catalyst (containing 52.8% water, 250 mg), and the suspension was stirred in an oil bath at 40° C. for 1.5 hours in hydrogen gas atmosphe... | CC(C)(C)OC(=O)N[C@@]1(C)CNC[C@H]1CF | null | null | null |
179,287 | ord_dataset-4d84abdf99524e0fb6c42ab2a3300790 | null | 1988-01-01T00:10:00 | true | [Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[N:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.[C@@H:12]1(N2C=CC(=O)NC2=O)[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[C@H:13]1[OH:14].[N-]=[N+]=[N-].[K+]>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([C@@H:12]3[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[C@H:13]... | O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 | Clc1cc(Cl)c2nc[nH]c2n1 | null | O=P([O-])([O-])[O-] | [K+] | [N-]=[N+]=[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 | 5,7-Dichloro-3H-imidazo[4,5-b]pyridine (0.0053 mole, 1.0 g) and uridine (0.00795 mole, 1.94 g), were suspended in 20 ml potassium phosphate, 0.01M at pH 7 with 0.04% potassium azide. The catalysts, purine nucleoside phosphorylase (1900 units) and uridine phosphorylase (1300 units) were added and the suspension mixed fo... | OC[C@H]1O[C@@H](n2cnc3c(Cl)cc(Cl)nc32)[C@H](O)[C@@H]1O | null | null | null |
36,415 | ord_dataset-3e699bae9dce4a0f996c34a7c5a4b79a | null | 1978-01-01T00:02:00 | true | Cl[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[N:11][C:6]=2[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1.[CH2:15]([NH:17][CH2:18][CH3:19])[CH3:16]>>[CH2:15]([N:17]([CH2:18][CH3:19])[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[N:11][C:6]=2[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1)[CH3:16] | CCNCC | Clc1nc2ccnn2c2ncccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2.04 g. of 5-chloropyrazolo[1,5-a]pyrido[3,2-e]pyrimidine of Example 1c are added to 20 ml. of diethylamine. The solution is refluxed for 5 hours. The excess diethylamine is distilled off and the residue is treated with 5 ml. water and extracted three times with 10 ml. portions of ethyl acetate. The organic layers are ... | CCN(CC)c1nc2ccnn2c2ncccc12 | null | null | null |
566,818 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | C(OC([N:8]1[CH2:13][CH2:12][C:11]2=[C:14]([CH:17]=[O:18])[NH:15][CH:16]=[C:10]2[C:9]1=[O:19])=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[O:19]=[C:9]1[C:10]2=[CH:16][NH:15][C:14]([CH:17]=[O:18])=[C:11]2[CH2:12][CH2:13][NH:8]1 | CC(C)(C)OC(=O)N1CCc2c(c[nH]c2C=O)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A mixture of 1-formyl-4-oxo-2,4,6,7-tetrahydro-pyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester (1.2 g, 4.54 mmol) in 50% of trifluoroacetic acid in dichloromethane was stirred at room temperature for 30 minutes. The reaction was concentrated and the residue was recrystallized from dichloromethane to give 400 ... | O=Cc1[nH]cc2c1CCNC2=O | null | 53.7 | null |
830,706 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:26]2([OH:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:25])[O:20]CCCC)[CH2:14][CH2:13]2)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].B>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:26]2([OH:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:10][N:... | CCCCOC(=O)NC1CCN(C(=O)C(c2ccc(Cl)c(Cl)c2)C2(O)CCCCC2)CC1 | null | null | B | 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 | 74 | null | A solution of tent-butyl {1-[(3,4-dichlorophenyl)(1-hydroxycyclohexyl)acetyl]piperidin-4-yl}carbamate (364 mg, 0.75 mmol) in dry tetrahydrofuran (1 mL), under nitrogen, was treated with a solution of borane (1.0 M in tetrahydrofuran, 2.62 mL, 2.62 mmol). The reaction was heated at 74° C. for 2 h, after which time the r... | CC(C)(C)OC(=O)NC1CCN(CC(c2ccc(Cl)c(Cl)c2)C2(O)CCCCC2)CC1 | null | 105.8 | null |
13,458 | ord_dataset-7f88a5da29d74264aae5239be74b3981 | null | 1976-01-01T00:10:00 | true | CO[C:3](=[O:18])[C@H:4]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[NH2:5].[CH3:19][N:20]=[C:21]=[S:22]>>[C:14]([O:13][C:11]([NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:4]1[NH:5][C:21](=[S:22])[N:20]([CH3:19])[C:3]1=[O:18])=[O:12])([CH3:15])([CH3:16])[CH3:17] | CN=C=S | COC(=O)[C@@H](N)CCCCNC(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using an analogous procedure to Example 1 Nε-t-butyloxycarbonyl-L-lysine methyl ester may be reacted with methyl isothiocyanate to give the title compound. | CN1C(=O)C(CCCCNC(=O)OC(C)(C)C)NC1=S | null | null | null |
1,470,235 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([F:12])[CH:3]=1.CO[C:15](OC)([N:17]([CH3:19])[CH3:18])C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([C:9](=[O:11])[CH:10]=[CH:15][N:17]([CH3:19])[CH3:18])=[C:6]([F:8])[CH:7]=1 | COC(C)(OC)N(C)C | CC(=O)c1c(F)cc(Br)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1-(4-bromo-2,6-difluorophenyl)ethanone (prepared according to the method described in PCT Patent Publication WO 2004/72070; 4.56 g, 19.4 mmol) and N,N-dimethylacetamide dimethyl acetal (6.94 g, 58.2 mmol) in toluene (45 mL) was refluxed for 16 h. The reaction mixture was then concentrated under reduced pre... | CN(C)C=CC(=O)c1c(F)cc(Br)cc1F | null | null | null |
25,172 | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | null | 1977-01-01T00:05:00 | true | [CH3:1][C:2]1([CH3:27])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:26])=[CH:12][C:13]([C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([CH3:19])[CH2:16][CH2:17][CH3:18])=[CH:14][C:4]=2[O:3]1.[ClH:28].[O:29]1[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][C:38](O)=[O:39])[CH2:31][CH2:30]1.C1(N=C=NC2CCCCC2)... | O=C(O)CCCN1CCOCC1 | CCCC(C)(c1ccccc1)c1cc(O)c2c(c1)OC(C)(C)C1=C2CCC1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | 1.0 g. (3.5 mmoles) of 4,4-dimethyl-9-hydroxy-7-(phenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta[c][1]benzopyran, 0.76 g. (3.63 mmoles) of γ-morpholinobutyric acid hydrochloride and 0.76 g. (3.70 mmoles) of dicyclohexylcarbodiimide are combined in 75 ml. of methylene chloride and stirred at room temperature for 24 h... | CCCC(C)(c1ccccc1)c1cc(OC(=O)CCCN2CCOCC2)c2c(c1)OC(C)(C)C1=C2CCC1 | null | null | null |
617,921 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:13]([O:12][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([Cl:8])=[CH:7][C:2]=1[NH2:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1 | Nc1cc(Cl)c([N+](=O)[O-])cc1O | BrCc1ccccc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | Synthesis of the compounds of general class III begins with the reaction of 2-amino4-chloro-5-nitrophenol at 0-50° C., preferably at room temperature, with benzyl bromide in the presence of potassium carbonate and tetra-N-butylammonium iodide in DMF to give 2-benzyloxy-5-chloro-4-nitroaniline in 56% yield. Subsequent r... | Nc1cc(Cl)c([N+](=O)[O-])cc1OCc1ccccc1 | null | 56 | null |
973,485 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[OH:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(O[BH-](OC(=O)C)... | CC(C)(C)OC(=O)n1c(-c2ccc(Cl)c3c2C(=O)NC3)cc2cc(C=O)ccc21 | OCCOCCN1CCNCC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | In a similar manner to Step 1 of Example 56, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (20.0 mg, 0.0487 mmol) was dissolved in dichloromethane (0.5 mL). The solution was treated with 1-[2-(2-hydroxyethoxy)ethyl]piperazine (35 mg, 0.20 mmol) and sodium triacetoxyborohydride (32 mg, 0.15 mmol) ... | CC(C)(C)OC(=O)n1c(-c2ccc(Cl)c3c2C(=O)NC3)cc2cc(CN3CCN(CCOCCO)CC3)ccc21 | null | null | null |
1,710,143 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[N:12]3[N:22]=[CH:23][C:24]([CH:25]=[C:26]4[NH:30][C:29](=[O:31])[NH:28][C:27]4=[O:32])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.CC(O)=O.[CH3:37][C:38]([CH3:40])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[... | O=C1NC(=O)C(=Cc2cnn3c(NC4CCNCC4)cc(Nc4cccc(Cl)c4)nc23)N1 | CC(C)=O | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 60 | null | To 5-((5-(3-chlorophenylamino)-7-(piperidin-4-ylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (20 mg, 0.04 mmol) in THF and AcOH (4.8 mg, 0.08 mmol) was added acetone (2.0 mL, 0.2 mmol) and sodium triacetoxy borohydride (85.0 mg, 0.4 mmol). The mixture was heated at 60° C. for one hour. Saturate... | CC(C)N1CCC(Nc2cc(Nc3cccc(Cl)c3)nc3c(C=C4NC(=O)NC4=O)cnn23)CC1 | null | null | null |
502,672 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | C[O-].[Na+].C([O:6][C:7](=O)[CH2:8][C:9](=O)[CH3:10])C.[N+]([O-])([O-])=O.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:29][C:30]([NH2:32])=[NH2+:31])[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26]>CO>[CH3:10][C:9]1[N:32]=[C:30]([NH:29][C:21]2[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH... | CCOC(=O)CC(C)=O | COc1cc(NC(N)=[NH2+])cc(OC)c1OC | null | C[O-] | O=[N+]([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 | 25 | null | To a solution of sodium methoxide (0.96 g, 1.79 mmol) in methanol was added ethyl-3-oxo-butanoate (0.23 g, 1.79 mmol) and 3,4,5-trimethoxyphenylguanidinium nitrate (0.5 g, 1.79 mmol). The mixture was stirred at reflux for 17 h. The reaction mixture was cooled to room temperature and evaporated in vacuo to give a dark g... | COc1cc(Nc2nc(C)cc(=O)[nH]2)cc(OC)c1OC | null | 47.9 | null |
1,311,958 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [C:1]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:47])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:46])[CH2:21][CH2:22][NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30](=[O:45])[N:31]([CH2:33][CH2:34][CH2:35][N:36](C(OC(C)(C)C)=O)[CH3:37])[CH3:32])=... | CN(CCN1CCC(OC(=O)Nc2ccccc2-c2ccccc2)CC1)C(=O)CCNc1ccc(C(=O)N(C)CCCN(C)C(=O)OC(C)(C)C)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 6 | The compound (150 mg, 0.21 mmol) obtained in Example 94b was dissolved in ethanol (0.5 mL), a 4 N hydrochloric acid-1,4-dioxane solution (5.1 mL, 20.6 mmol) was added, and the mixture was stirred at room temperature under a nitrogen atmosphere for 6 hours. After the reaction was completed, the solvent was evaporated un... | CNCCCN(C)C(=O)c1ccc(NCCC(=O)N(C)CCN2CCC(OC(=O)Nc3ccccc3-c3ccccc3)CC2)cc1 | null | 74.2 | null |
1,324,051 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH3:20]O>>[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([O:13][CH3:20])=[O:12] | CO | CC1=C(C(=O)O)N2C(=O)C(N)C2SC1 | 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 | 75 | null | 7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1 g, 4.67 mmol) was suspended in methanol (20 mL) before treating with conc. sulphuric acid (0.1 ml, 1.876 mmol) and heated at reflux (75° C.) for 16 hours, under argon. After heating for 15 minutes all the remaining solid had dissolved to fo... | COC(=O)C1=C(C)CSC2C(N)C(=O)N12 | null | null | null |
1,650,220 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | S1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[C:11]([F:13])[C:10]([C:14]3[N:19]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:16][C:15]=3[F:24])=[C:9]([F:25])[CH:8]=2)[CH2:3][CH2:2]1.O[O:27][S:28]([O-:30])=O.[K+]>C(Cl)Cl>[O:27]=[S:28]1(=[O:30])[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[C:11]([F:13])[C:10]([C:14]3[N:19]=[C:18]([C:20]... | COC(=O)c1ccc(F)c(-c2c(F)cc(C3=CCSCC3)cc2F)n1 | O=S([O-])OO | null | [K+] | 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 | 8 | To a solution of methyl 6-(4-(3,6-dihydro-2H-thiopyran-4-yl)-2,6-difluorophenyl)-5-fluoropicolinate (1.0 equiv.) in DCM (0.10 M) at rt was added oxone (6.0 equiv.) in one portion. The resulting mixture was stirred at RT overnight, and then refluxed at 40° C. for 4 hrs. 10.0 equiv. of oxone were added and the reaction w... | COC(=O)c1ccc(F)c(-c2c(F)cc(C3=CCS(=O)(=O)CC3)cc2F)n1 | null | 100 | null |
662,760 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | [OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=O)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][C:14]=1[O:21][CH3:22].[NH2:24][CH2:25][CH2:26][SH:27]>C(O)C>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10]1[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:2... | COc1cc(SC)ccc1/C=C/C(=O)c1c(O)cc(C)oc1=O | NCCS | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 80 | null | 4-Hydroxy-3-[(E)-3-(2-methoxy-4-methylsulfanyl-phenyl)-acryloyl]-6-methyl-pyran-2-one (41.8 mg, 0.126 mmol), prepared as in Reference 5, Step 5.1, was dissolved in absolute ethanol (5 mL) and then 2-aminoethanethiol (9.8 mg, 0.126 mmol) was added to the solution. The mixture was stirred at 80° C. The progress of the re... | COc1cc(SC)ccc1C1CC(c2c(O)cc(C)oc2=O)=NCCS1 | null | 41.6 | null |
1,159,126 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C@@H:14]([NH2:19])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1>>[C:1]([O:5][C:6](=[O:20])[... | Cc1ccc(-c2ccc(S(=O)(=O)Cl)cc2)cc1 | CC(C)(C)OC(=O)COc1cccc2c1CCC[C@H]2N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | Starting from (R)-(5-amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (28 mg, 0.1 mmol), triethylamine (0.02 mL, 0.11 mmol) and 4′-methyl-biphenyl-4-sulfonyl chloride (29 mg, 0.11 mmol), using the method analogous to the one for example 1-1, method A, 4th step, crude [(R)-5-(4′-methyl-biphenyl-... | Cc1ccc(-c2ccc(S(=O)(=O)N[C@@H]3CCCc4c(OCC(=O)OC(C)(C)C)cccc43)cc2)cc1 | null | null | null |
467,114 | ord_dataset-8cd3720738054d76b936f66e14d8cba6 | null | 2000-01-01T00:06:00 | true | [CH2:1]([O:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]([NH:11][C:12]1[C:13]([CH2:21][CH2:22][CH3:23])=[N:14][N:15]([CH3:20])[C:16]=1[C:17]([NH2:19])=[O:18])=O)[CH3:2].[OH-].[Na+]>C(O)C.O>[CH2:1]([O:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]1[NH:19][C:17](=[O:18])[C:16]2[N:15]([CH3:20])[N:14]=[C:13]([CH2:21][CH2:22][CH3:23])[C:1... | CCCc1nn(C)c(C(N)=O)c1NC(=O)c1sccc1OCC | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of 3 (1.15 g, 3.42 mmol), NaOH (284 mg, 7.1 mmol) in ethanol (11 mL) and water (34 mL) was heated at 80° C. for 65 h. After cooling to r.t. a white precipitate was formed. Filtration and drying under vacuum gave 0.625 g of the product. The filtrate was extracted with CH2Cl2, and the organic phase was washed w... | CCCc1nn(C)c2c(=O)[nH]c(-c3sccc3OCC)nc12 | null | 57.4 | null |
713,537 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[N+:10]([C:13]1[CH:14]=[CH:15][C:16](O)=[N:17][CH:18]=1)([O-:12])=[O:11].C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.CO>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][O:6][C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][N:17]=1 | OCc1cccc(F)c1 | O=[N+]([O-])c1ccc(O)nc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | 120 | null | A mixture of 3-flouro-benzyl alcohol (1.07 g, 8.48 mmol), 5-nitro-pyridin-2-ol (1.34 g, 8.48 mmol) and K2CO3 (1.41 g, 10.2 mmol) in DMA (10 ml) was heated at 120° C. for 7 h. The mixture was cooled to rt, diluted with MeOH(10 ml), filtered and purified by preparative HPLC to give 13A (1.01 g, 48%). | O=[N+]([O-])c1ccc(OCc2cccc(F)c2)nc1 | null | 48 | null |
223,576 | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | null | 1991-01-01T00:02:00 | true | [Br:1][CH2:2][CH:3]1[C:8]2[C:9]([CH3:15])=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:7]=2[CH2:6][CH:5]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[O:4]1.[Br:22]Br.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:22][C:11]1[CH:10]=[C:9]([CH3:15])[C:8]2[CH:3]([CH2:2][Br:1])[O:4][CH:5]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)... | COc1ccc(C)c2c1CC(C1CCCCC1)OC2CBr | BrBr | null | O=S([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2.04 g (5.8 mmol) of 1-bromomethyl-3-cyclohexyl-3,4-dihydro-5-methoxy-8-methyl-1H-2-benxopyran (the product of Step 2 of Example 33) in 20 mL of dry methylene chloride was cooled to 0° C. and treated with 0.38 mL (7.4 mmol) of bromine. The resultant solution was stirred for 25 minutes at 0° C. and then po... | COc1c(Br)cc(C)c2c1CC(C1CCCCC1)OC2CBr | null | 55 | null |
1,561,231 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].[CH2:24]([N:26]([CH3:30])[C:27](Cl)=[O:28])[CH3:25]>>[CH2:24]([N:26]([CH3:30])[C:27]([N:13]1[CH2:14][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH3:2]... | CCN(C)C(=O)Cl | CCc1ccc(C2CNCC(C(=O)Nc3ccccc3)C2)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 | 250 mg (0.74 mmol) of 5-(4-ethylphenyl)-N-phenylpiperidine-3-carboxamide (Example 17A) and 117 mg (0.96 mmol, 1.3 eq.) of ethyl(methyl)carbamoyl chloride were reacted according to General Method 3. Yield: 215 mg (74% of theory) | CCc1ccc(C2CC(C(=O)Nc3ccccc3)CN(C(=O)N(C)CC)C2)cc1 | null | null | null |
164,926 | ord_dataset-12ef86aced0149e0917be82ce22190e2 | null | 1987-01-01T00:11:00 | true | [CH2:1]([NH:8][S:9](=[O:12])(=O)[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:14]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][S:9]([Cl:14])(=[O:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | O=S(=O)(O)NCc1ccccc1 | ClP(Cl)(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A stirred mixture of benzylsulfamic acid (73 g), PCl5 (81 g) in toluene (540 ml) is heated to 40°-50° C. for one hour and refluxed for about 3 hours. The cooled mixture is filtered through Celite and the filtrate concentrated in vacuo to remove the toluene affording the desired product as a liquid. | O=S(=O)(Cl)NCc1ccccc1 | null | null | null |
1,683,460 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1.[OH:11]O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:11])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1 | OO | Clc1cnc2c(c1)CCC2 | 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 | 70 | 8 | A solution of 3-chloro-6,7-dihydro-5H-[1]pyrindine (3.03 g, 19.7 mmol) in acetic acid (19.7 ml) was treated at room temperature with hydrogen peroxide (3.45 ml, 39.5 mmol). The mixture was heated to 70° C. and stirred at this temperature overnight. After completion, the reaction mixture was allowed to cool and was conc... | [O-][n+]1cc(Cl)cc2c1CCC2 | null | null | null |
1,058,924 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][C:13](=[O:15])[NH:14][C:7]=12.[F:19][C:20]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][C:21]=1[C:22](Cl)=[O:23]>>[O:15]=[C:13]1[NH:12][C:8]2=[N:9][CH:10]=[CH:11][C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:2... | O=C(Cl)c1cc(OC(F)(F)F)ccc1F | Nc1cccc(Oc2ccnc3[nH]c(=O)[nH]c23)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 | Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 2-fluoro-5-trifluoromethoxy-benzoyl chloride to afford the title compound (11 mg, 11.7%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=5.9 Hz), 6.91-6.94 (m, 1H, Harom), 7.41-7.44 (m, 2H, Harom), 7.50-7.53 (m, 2H, Harom), 7.67-7.69 (m, ... | O=C(Nc1cccc(Oc2ccnc3[nH]c(=O)[nH]c23)c1)c1cc(OC(F)(F)F)ccc1F | null | 11.7 | null |
1,120,743 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | FC1C=CC=CC=1CCN[C:11]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:12].[CH2:19]([C:26]1([N:33]([CH3:35])[CH3:34])[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(N=C=NC(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)C>[CH2:19]([C:26]1([N:33]([CH3:34])[CH3:35])[CH2:31][... | O=C(O)CCCC(=O)NCCc1ccccc1F | CN(C)C1(Cc2ccccc2)CCC(N)CC1 | null | CC(C)N=C=NC(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | As described for Example 341, 0.95 mg 4-[2-(2-fluorophenyl)ethylcarbamoyl]butyric acid and 0.87 1-benzyl-N,N-dimethylcyclohexane-1,4-diamine were converted in 5 ml DMF in the presence of 0.59 ml N,N-diisopropylcarbodiimide and 0.50 g 1-hydroxybenzotriazole and the crude product (1.65 g yellow solid) similarly isolated.... | CN(C)C1(Cc2ccccc2)CCC(NC(=O)CCCC(=O)O)CC1 | null | null | null |
271,957 | ord_dataset-347c0709d28a44dea43ca42052be4db3 | null | 1993-01-01T00:07:00 | true | [C:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[C:1]1([C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[O:13][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | COC(=O)CBr | Oc1cccc(-c2ccccc2)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 5 | A mixture of 3-phenylphenol (5.00 g), methyl bromoacetate (3.1 ml) and potassium carbonate (8.1 g) in DMF was stirred at room temperature. After five hours, the reaction mixture was diluted with water (100 ml) and then extracted with ether. The combined organic layers were washed with aqueous sodium carbonate followed ... | COC(=O)COc1cccc(-c2ccccc2)c1 | null | null | null |
381,356 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Cl:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:1... | Oc1ccc(C(=Cc2ccccc2)c2ccccc2)cc1 | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | Combine (E and Z)-1-[(4-hydroxy)phenyl]-1,2-diphenyl-ethylene [Cacchi et al, Tet. Lets. 25, 3137-3140 (1984)] (0.90 g, 3.31 mmol) and N-chlorosuccinimide (0.486 g, 3.64 mmol) in chloroform (20 mL). Heat to reflux and allow to stir at reflux for 48 hours. Evaporate in vacuo. Chromatograph on silica gel eluting with 20% ... | Oc1ccc(C(=C(Cl)c2ccccc2)c2ccccc2)cc1 | null | null | null |
1,021,642 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:13](=O)([O-])O.[Na+]>CO.S(=O)(=O)(O)O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1 | O=C(O)CCc1ccc(O)cc1 | O=C([O-])O | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 16 | 15 g (0.09 mol, 1 eq) of 3-(4-hydroxyphenyl)propanoic acid are dissolved in 50 ml of methanol and 4 drops of sulfuric acid are added. The reaction mixture is stirred for 16 hours at room temperature. The reaction is stopped by addition of 50 mL of saturated sodium hydrogen carbonate solution and then extracted with eth... | COC(=O)CCc1ccc(O)cc1 | null | 92 | null |
1,331,217 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [O:1]=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)=[O:6].[S:21](Cl)(Cl)=O>>[C:2]([C:3]1[S:21][N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:5](=[O:6])[CH:4]=1)(=[O:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | Cc1ccc(NC(=O)CCC(=O)c2ccccc2)cc1 | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-oxo-4-phenyl-N-p-tolyl-butyramide 28 (252 mg, 0.944 mmol) in thionyl chloride (1 mL) was stirred for 16 h at room temperature. Excess thionyl chloride was removed under vacuum and the residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1) to give the compound 2... | Cc1ccc(-n2sc(C(=O)c3ccccc3)cc2=O)cc1 | null | 77 | null |
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