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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
513,503 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [CH3:1][N:2]([CH3:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][C:15]([C:19](O)=[O:20])=[CH:14][C:13]=3[CH:22]=2)=[CH:5][CH:4]=1.[CH3:24][N:25]([CH2:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1)[CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O... | CN(C)c1ccc(-c2ccc3c(c2)C=C(C(=O)O)CCO3)cc1 | CN(Cc1ccc(N)cc1)C1CCOCC1 | null | CCOP(=O)(C#N)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 7-(4-dimethylaminophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (0.15 g), 4-(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)aniline (0.11 g) and triethylamine (0.2 ml) in dimethylformamide (15 ml) was added diethyl cyano-phosphate (0.11 ml) under ice-cooling, and the mixture was stirred under nitro... | CN(C)c1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(CN(C)C4CCOCC4)cc2)CCO3)cc1 | null | 28.2 | null |
1,348,903 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([NH:14][CH2:15][C:16]([F:19])([F:18])[F:17])[CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][C:4]=1[NH2:20].Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N:35]2[CH:39]=[CH:38][CH:37]=[N:36]2)[C:25]([Cl:40])=[CH:24][N:23]=1>>[Cl:40][C:25]1[C:26]([NH:28][C:... | Clc1ncc(Cl)c(Nc2ccccc2-n2cccn2)n1 | COc1c(N)ccc2c1CCC(NCC(F)(F)F)CC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In an analogous procedure to Example 651, part c, 1-Methoxy-N*7*-(2,2,2-trifluoro-ethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine was combined with (2,5-dichloro-pyrimidin-4-yl)-(2-pyrazol-1-yl-phenyl)-amine to yield -Chloro-N*2*-[1-methoxy-7-(2,2,2-trifluoro-ethylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepte... | COc1c(Nc2ncc(Cl)c(Nc3ccccc3-n3cccn3)n2)ccc2c1CCC(NCC(F)(F)F)CC2 | null | 63 | null |
943,052 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[N:10]([C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])[C:11](=[O:14])[NH:12][CH2:13][C:3]=12.[CH3:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][C:25]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[NH2:28][C:27]1[CH:26]=[CH:25][C:24]([CH3:23])=[C:3... | CSc1nc(Cl)c2c(n1)N(c1c(F)cccc1F)C(=O)NC2 | Cc1ccc(N)cc1B1OC(C)(C)C(C)(C)O1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 95 | null | To 5-chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (0.342 g, 1 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.256 g, 1.1 mmol) in dioxane (40 mL), was added a solution of K2CO3 (0.417 g, 3 mmol) in water (10 mL). Argon was vigorously bubbled thr... | CSc1nc(-c2cc(N)ccc2C)c2c(n1)N(c1c(F)cccc1F)C(=O)NC2 | null | null | null |
263,684 | ord_dataset-a7bd0db0684c464bb02ff6a36065fee3 | null | 1993-01-01T00:03:00 | true | [S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[O:6]([CH2:13][CH:14]([OH:16])[CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[O:6]([CH2:13][CH:14]([O:16][S:1](=[O:4])(=[O:3])[NH2:2])[CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1 | CC(O)COc1ccccc1 | NS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by procedures of Example 22 from sulfamoyl chloride and 3-phenoxy-2-propanol through the partitioning and final evaporation to give an oil as residue. The oil was purified by chromatography using a 4.5 cm×100 cm glass column packed with 500 g of silica gel and methylene chloride as eluti... | CC(COc1ccccc1)OS(N)(=O)=O | null | null | null |
1,719,999 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)[CH2:3][OH:4].[N:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[CH:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)[N:25]=2)=[CH:20][CH:19]=1)=[C:16]=[S:17]>>[OH:4][CH2:3][CH:2]([NH:1][C:16]([NH:1... | NC(CO)c1ccc(C(F)(F)F)cc1 | FC(F)(F)c1ccc(-n2cnc(-c3ccc(N=C=S)cc3)n2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared with 2-amino-2-(4-(trifluoromethyl)phenyl)ethanol and 3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole and isolated as a white solid (1.54 g, quantitative): 1H NMR (300 MHz, CDCl3) δ 8.09 (s, 1H), 7.66 (d, J=8.7 Hz, 2H), 7.43 (d, J=6.3 Hz, 1H), 7.30 (d, J=8.4 Hz... | OCC(NC(=S)Nc1ccc(-c2ncn(-c3ccc(C(F)(F)F)cc3)n2)cc1)c1ccc(C(F)(F)F)cc1 | null | null | null |
887,484 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | I[CH2:2][C@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15].[CH2:17]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH2:18][CH2:19][CH3:20]>CC#N>[CH2:17]([CH:21]1[CH2:26][CH2:25][N:24]([CH2:2][C@H:3]([CH3:16])[CH2:4][N:5]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:... | C[C@@H](CI)CN1C(=O)COc2ccccc21 | CCCCC1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 60 | 72 | A 4 ml vial was charged with crude (R)-4-(3-iodo-2-methyl-propyl]-4H-benzo[1,4]oxazin-3-one (108LM46-43) (0.312 g) and 4-butyl-piperidine (0.210 g, 1.49 mmol) in dry MeCN (½ ml) and shaken at 60° C. for 3 days. The reaction mixture was quenched with water (1 ml), and the product extracted into EtOAc (2×1 ml). The combi... | CCCCC1CCN(C[C@H](C)CN2C(=O)COc3ccccc32)CC1 | null | 59.5 | null |
563,410 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | [NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:28]=[CH:27][C:8]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[O:17])[CH2:12][CH2:11]2)=[CH:7][CH:6]=1.C([Si]([O:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH2:54][CH:55]2[CH2:57][O:56]2)=[CH:49][CH:48]=1)(C1C=CC=CC=1)C... | CC(C)(C)[Si](Oc1ccc(OCC2CO2)cc1)(c1ccccc1)c1ccccc1 | NCCOc1ccc(NC2CCN(C(=O)NCc3ccc(F)cc3)CC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 4-[4-(2-Aminoethoxy)anilino]-N-(4-fluorobenzyl)-1-piperidinecarboxamide (0.63 g, 1.4 mmol) was reacted with tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.53 g, 1.3 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.125 g, 0.15 mmol). | O=C(NCc1ccc(F)cc1)N1CCC(Nc2ccc(OCCNC[C@H](O)COc3ccc(O)cc3)cc2)CC1 | null | 11.5 | null |
1,721,319 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1.[CH3:12][NH:13][C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15]>CN1C(=O)CCC1>[CH3:12][N:13]([C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1 | CN[C@H](C)c1ccccc1 | Cc1nnc2ccc(Cl)nn12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 200 | null | 6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine (150 mg, 0.890 mmol; commercially available or prepared according to patent WO2006/039325A2), (R)-N-methyl-1-phenylethanamine (481 mg, 3.56 mmol; available from Aldrich) and anhydrous NMP (1 mL) were charged into a microwave tube equipped with a magnetic stirbar. After... | Cc1nnc2ccc(N(C)[C@H](C)c3ccccc3)nn12 | null | null | null |
1,752,664 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C@H:6]([O:10][CH2:11][CH:12]=O)[CH2:7][CH:8]=[CH2:9].[OH:14][N:15]=CCOC([C@@H]1C[C@H]1C)CC=C>>[OH:14][N:15]=[CH:12][CH2:11][O:10][C@@H:6]([C@@H:2]1[CH2:3][CH2:4][CH2:5][O:1]1)[CH2:7][CH:8]=[CH2:9] | C=CCC(OCC=NO)[C@@H]1C[C@H]1C | C=CC[C@@H](OCC=O)[C@@H]1CCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ({(1R)-1-[(2S)-Tetrahydrofuran-2-yl]but-3-en-1-yl}oxy)acetaldehyde (C97) was converted to the product using the method described for the synthesis of N-hydroxy-2-({1-[(1R,2R)-2-methylcyclopropyl]but-3-en-1-yl}oxy)ethanimine (C84) in Example 20. Yield: 4.7 g, 23.6 mmol, 65% over 2 steps from (C95). | C=CC[C@@H](OCC=NO)[C@@H]1CCCO1 | null | null | null |
1,105,417 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [C:1]([O-:4])([O-])=[O:2].[K+].[K+].Br[C:8]1([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:18]>O1CCOCC1>[Cl:17][C:13]1[CH:12]=[C:11]2[C:16]([C:8]([NH:10][CH:9]([CH2:8][CH:16]([CH3:11])[CH3:15])[C:1]([OH:4])=[O:2])([CH2:19][C:20]3[C... | O=C1Nc2cc(Cl)ccc2C1(Br)Cc1cccc(Cl)c1 | O=C([O-])[O-] | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To the aqueous solution K2CO3 (1.6 μL, 1N) was added (2S)-amino-4-methyl-pentanoic (106 mg, 0.81 mmol), then followed by the addition of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (200 mg, 0.54 mmol) in dioxane (5 mL). After the mixture was stirred at room temperature for 4 h, the reaction mixture... | CC(C)CC(NC1(Cc2cccc(Cl)c2)C(=O)Nc2cc(Cl)ccc21)C(=O)O | null | null | null |
1,737,765 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38]>CS(C)=O.O>[C:11]1([C:8]2[N:6]3[N:7]=[C:2]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38])[CH:3]=[CH:4... | NCCCCO | Clc1ccc2ncc(-c3cccc4ccccc34)n2n1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 100 | null | To a solution of 6-chloro-3-(naphthalen-1-yl)imidazo[1,2-b]pyridazine (50 mg, 0.179 mmol, 1.0 equiv) in DMSO (2.0 mL) was added p-toluene sulfonic acid monohydrate (35 mg, 0.184 mmol, 1.0 equiv) and 4-aminobutan-1-ol (200 mg, 2.24 mmol, 12.5 equiv) and heated to 100° C. for 24 h. The reaction mixture was diluted with w... | OCCCCNc1ccc2ncc(-c3cccc4ccccc34)n2n1 | null | 50.4 | null |
1,080,183 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | FC(F)(F)C(O)=O.[C:8]([NH:16][C:17]1[CH:29]=[C:28]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:8]([NH:16][C:17]1[CH:29]=[C:28]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=... | CC(C)(C)OC(=O)c1ccc(CCCCc2ccccc2)cc1NC(=O)c1ccccc1 | 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 | null | 4.9 mL solution of trifluoroacetic acid containing 0.50 g of tert-butyl 2-(benzamido)-4-(4-phenylbutyl)benzoate was stirred at room temperature for 2 hours and 30 minutes. A solid substance was separated by filtration to obtain 0.16 g of 2-(benzamido)-4-(4-phenylbutyl)benzoic acid as white solid. | O=C(Nc1cc(CCCCc2ccccc2)ccc1C(=O)O)c1ccccc1 | null | null | null |
1,413,267 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH:10]12[O:16][CH:15]1[CH2:14][CH2:13][CH2:12][CH2:11]2>C(O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C@@H:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:15]2[OH:16])=[CH:5][CH:4]=1 | C1CCC2OC2C1 | Oc1ccc(Br)cc1 | null | [Na] | 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 | Sodium metal (2.58 g, 112 mmol) was combined with absolute ethanol (200 mL) and allowed to react completely. 4-Bromophenol (19.4 g, 112 mmol) was added, and the reaction was stirred for 20 minutes, at which point 7-oxabicyclo[4.1.0]heptane (10.0 g, 102 mmol) was added, and the solution was heated at reflux for 15 hours... | O[C@@H]1CCCC[C@H]1Oc1ccc(Br)cc1 | null | null | null |
645,406 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [C:1]1([S:7]([N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([O:23][CH2:24][CH:25]4[CH2:27][O:26]4)[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][O:29][C:30]1[CH:39]=[CH:38][CH:37]=[CH:36][C:31]=1[O:32][CH2:33][CH2:34][NH2:35]>>[C:1]1([S:7]([N:10]2[C:22]3[C... | COc1ccccc1OCCN | O=S(=O)(c1ccccc1)n1c2ccccc2c2c(OCC3CO3)cccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | reaction of 9-benzenesulfonyl-4-oxiranylmethoxy-9H-carbazole with benzyl-[2-(2-methoxy-phenoxy]-ethyl-amine to give a 1-(9-benzenesulfonyl-9H-carbazol-4-yloxy)-3-{benzyl-[2-(2-methoxy-phenoxy)ethyl]-amino}-propan-2-ol; | COc1ccccc1OCCN(Cc1ccccc1)CC(O)COc1cccc2c1c1ccccc1n2S(=O)(=O)c1ccccc1 | null | null | null |
850,368 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | Br[C:2]1[C:3]([O:10][CH3:11])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH3:9].[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.C1COCC1>[CH3:11][O:10][C:3]1[C:2]([C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)=[C:7]([O:8][CH3:9])[N:6]=[CH:5][N:4]=1 | COc1ncnc(OC)c1Br | OB(O)c1ccncc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCO | null | null | null | null | null | null | null | null | null | 70 | null | A mixture of 5-bromo-4,6-dimethoxypyrimidine (2.18 g, 10 mmol), pyridine-4-boronic acid (1.85 g, 15 mmol), K2CO3 (2.76 g, 20 mmol), and PXPd (539 mg, 1.0 mmol) in ethanol/THF (1:1, 25 mL) under argon was heated at 70° C. for 3 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture w... | COc1ncnc(OC)c1-c1ccncc1 | null | 82.4 | null |
1,069,933 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[NH:14][C:15]([NH2:24])=[C:16]2[C:20]([N:21]=1)=[N:19][C:18]([O:22][CH3:23])=[N:17]2)[CH2:9][CH2:10][CH3:11].Br[CH2:26][CH2:27][C@@H:28]1[CH2:32][CH2:31][O:30][CH2:29]1>>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:26][CH2:27][C@@H:28]2[CH2:32][C... | BrCC[C@@H]1CCOC1 | CCCCOc1nc2nc(OC)nc-2c(N)[nH]1 | 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 | null | Prepared similarly to Intermediate 215 from 2-(butyloxy)-8-(methyloxy)-1H-purin-6-amine trifluoroacetate and (3S)-3-(2-bromoethyl)tetrahydrofuran. | CCCCOc1nc(N)c2nc(OC)n(CC[C@@H]3CCOC3)c2n1 | null | null | null |
1,174,713 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [CH2:1]([C:8]1([C:21](=[O:35])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])[CH:24]=2)[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>CO>[CH3:33][N:31]([CH3:32])[C:30](=[O:34])[O:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:2... | CN(C)C(=O)Oc1cccc(NC(=O)C2(Cc3ccccc3)CCN(C(=O)OC(C)(C)C)CC2)c1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1COCCO1 | null | null | null | null | null | null | null | null | null | 50 | null | To a solution of tert-butyl 4-benzyl-4-(3-(dimethylcarbamoyloxy)-phenylcarbamoyl)piperidine-1-carboxylate from step A (0.162 g, 0.336 mmol) in MeOH (5 mL) was added 4 M HCl in dioxane (0.250 mL, 1.00 mmol). The reaction was heated at 50° C. for 1 hour, and then concentrated under vacuum, re-dissolved in MeOH and re-con... | CN(C)C(=O)Oc1cccc(NC(=O)C2(Cc3ccccc3)CCNCC2)c1 | null | null | null |
252,281 | ord_dataset-49bd993346b64eeeb2a8fe2643164a0a | null | 1992-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([N:15]2[C:19](=[O:20])[N:18]([CH2:21][CH2:22][CH3:23])[N:17]=[N:16]2)=[CH:10][C:3]=1[O:4][CH2:5][C:6]([O:8]C)=[O:7].[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([N:15]2[C:19](=[O:20])[N:18]([CH2:21][CH2:22][CH3:23])[N:17]=[N:16]2)=[CH:10][C:3]=1[O:4][CH2:5][C:6... | CCCn1nnn(-c2cc(OCC(=O)OC)c(Cl)cc2Cl)c1=O | null | null | Cl | [Na+] | [OH-] | 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 | A stirred solution of 0.5 g (0.0014 mole) of methyl 2,4-dichloro-5-(1,4-dihydro-5-oxo-4-propyltetrazol-1-yl)phenoxyacetate (compound 83) and 0.08 g (0.0021 mole) of sodium hydroxide in 10 mL of methanol was heated at reflux temperature for 1.5 hours. The reaction mixture was cooled, then evaporated under reduced pressu... | CCCn1nnn(-c2cc(OCC(=O)O)c(Cl)cc2Cl)c1=O | null | 41.2 | null |
1,494,799 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]([CH3:33])[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:20]([CH3:31])[CH2:19]3)=[C:13]([F:32])[CH:12]=2)=[O:9])=[CH:4][CH:3]=1.[F:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1>>[F:32][C:1... | Oc1ccc(F)cc1 | C[C@H]1CN(Cc2ccc(N(C)C(=O)c3ccc(Cl)nc3)cc2F)CCN1C(=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 | 8 | The title compound was prepared from 1,1-dimethylethyl (2S)-4-({4-[[(6-chloro-3-pyridinyl)carbonyl](methyl)amino]-2-fluorophenyl}methyl)-2-methyl-1-piperazinecarboxylate (D70) and 4-fluorophenol using a method similar to that described for D55 in Description 55 although the reaction temp./time was 130° C. for 8 h and p... | C[C@H]1CN(Cc2ccc(N(C)C(=O)c3ccc(Oc4ccc(F)cc4)nc3)cc2F)CCN1C(=O)OC(C)(C)C | null | null | null |
582,199 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [O-:1][CH2:2][CH3:3].[Na+].F[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[O:12][CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18].O>C(O)C>[CH2:2]([O:1][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[O:12][CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH3:3] | C[Si](C)(C)CCOCOc1cnccc1F | CC[O-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | 48 | To a stirred solution of sodium ethoxide (0.9 g, 13 mmol) in ethanol (10 mL) was added all at once 10 (1.07 g, 4.4 mmol). The resulting mixture was stirred at room temperature for 48 hours, then poured into water (100 mL). The resulting mixture was extracted with ether (3×50 mL). The ether extracts were combined, dried... | CCOc1ccncc1OCOCC[Si](C)(C)C | null | 50.6 | null |
27,833 | ord_dataset-14866e68bb5b47f5929457eecb4eb3a5 | null | 1977-01-01T00:07:00 | true | [CH3:1][C:2]1[N+:11]([O-:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[N+:4]([O-:13])[C:3]=1[C:14]([O:16][CH3:17])=[O:15].[Br:18]Br.CO>CN(C)C=O>[Br:18][CH2:1][C:2]1[N+:11]([O-:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[N+:4]([O-:13])[C:3]=1[C:14]([O:16][CH3:17])=[O:15] | BrBr | COC(=O)c1c(C)[n+]([O-])c2ccccc2[n+]1[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 1.5 | Methyl 3-methyl-2-quinoxalinecarboxylate-1,4-dioxide (1.2 moles) were suspended in 475 ml of dimethylformamide and 64 ml of bromine was added dropwise with stirring over 1.5 hours while the temperature rose to 42° C. After additional stirring for 48 hours 1.5 liters of methanol were added and stirred for about 1/2 hour... | COC(=O)c1c(CBr)[n+]([O-])c2ccccc2[n+]1[O-] | null | null | null |
1,299,681 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)[CH:10]=[N:11][C:5]=2[N:4]2[CH2:28][CH2:29][CH2:30][C@@H:3]12.[CH3:31][CH2:32][N:33](C(C)C)C(C)C.C(N)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=... | O=C(O)c1ccc(N2CCN(Cc3cnc4c(c3)NC(=O)[C@@H]3CCCN43)CC2)cc1 | CCN(C(C)C)C(C)C | null | CCN | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | 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 | 2 | (S)-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzoic acid (75.0 mg, 0.184 mmol) was suspended in DMF (1.0 mL) and DIPEA (0.15 mL) was added followed by ethylamine (30 mg, 0.665 mmol) and HATU (85.0 mg, 0.224 mmol). The reaction mixture was stirred at ambient tempe... | CCNC(=O)c1ccc(N2CCN(Cc3cnc4c(c3)NC(=O)[C@@H]3CCCN43)CC2)cc1 | null | 30 | null |
1,648,120 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+].[Br:18][CH2:19][CH2:20][CH2:21]Br>CN(C=O)C.O>[Br:18][CH2:19][CH2:20][CH2:21][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1 | Cc1ccc(O)cc1[N+](=O)[O-] | BrCCCBr | 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 | 100 | null | A solution of 4-methyl-3-nitrophenol (1.00 g, 6.53 mmol) in DMF (6 mL) was treated with K2CO3 (0.903 g, 6.53 mmol) and 1,3-dibromopropane (6.63 mL, 65.3 mmol) and heated to 100° C. for 2.5 h. The cooled mixture was diluted with water and extracted with DCM. The combined organics were dried (MgSO4), filtered and evapora... | Cc1ccc(OCCCBr)cc1[N+](=O)[O-] | null | null | null |
688,798 | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | null | 2005-01-01T00:10:00 | true | [NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[H-].[Na+].[CH:10]1([CH2:16][CH2:17]Br)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH:10]1([CH2:16][CH2:17][N:1]2[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1 | O=Cc1c[nH]cn1 | BrCCC1CCCCC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | Imidazole-4-carboxaldehyde (4.8 g, 50 mmol) was added portionwise to a suspension of sodium hydride (2.20 g, 60% dispersion in mineral oil, 55 mmol) in tetrahydrofuran (150 ml), and the mixture was then stirred at room temperature for 1 hour. 2-Cyclohexylethyl bromide (8.6 ml, 55 mmol) was added, and the mixture was he... | O=Cc1cn(CCC2CCCCC2)cn1 | null | null | null |
1,324,817 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:12][S:13]([NH:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)(=[O:15])=[O:14]>>[NH2:11][C:9]1[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:21]3[CH:22]=[C:17]([NH:16][S:13]([CH3:12])(=[O:14])=[O:15])[CH:18]=[CH:19][CH:20]=3)[N:7]2[N:8]=1 | Nc1nc2cccc(Br)n2n1 | CS(=O)(=O)Nc1cccc(B(O)O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | N-[3-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-phenyl]-methanesulfonamide was prepared from 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.80 g, 8.45 mmol) and 3-methylsulfonylaminophenyl boronic acid (2.0 g, 9.30 mmol), in a manner analogous to Step 73c. The residue was purified on an 80 g Isco silica gel colum... | CS(=O)(=O)Nc1cccc(-c2cccc3nc(N)nn23)c1 | null | 18 | null |
644,942 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1.Cl.[OH-:23].[Na+]>>[NH2:1][C:2]1[NH:3][C:4](=[O:23])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[... | C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc2c(Cl)nc(N)nc21 | [OH-] | null | Cl | [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 | A mixture of product from Step B (90 mg, 0.3 mmol) in aqueous NaOH (2N, 9 mL) was heated at reflux temperature for 5 h, then neutralized at 0° C. with 2 N aqueous HCl and evaporated to dryness. Purification on a silica gel column with CH2Cl2/MeOH, 5/1 as eluent afforded the title compound as a white solid (70 mg). | C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc2c(=O)[nH]c(N)nc21 | null | null | null |
1,328,137 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:16]1([SH:32])[C:29]2[C:30]3=[C:31]4[C:26](=[CH:27][CH:28]=2)[CH:25]=[CH:24][CH:23]=[C:22]4[CH:21]=[CH:20][C:19]3=[CH:18][CH:17]=1>CN(C=O)C>[CH:18]1[C:19]2[C:30]3=[C:31]4[C:22](=[CH:21][CH:20]=2)[CH:23]=[CH:24][CH:25]=[C:26]4[CH:27]=[CH:28... | O=Cc1ccccc1F | Sc1ccc2ccc3cccc4ccc1c2c34 | 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 | 130 | null | 2-fluoro-benzaldehyde (477 mg, 3.8 mmol), potassium carbonate (700 mg, 5.0 mmol) and pyrene-1-thiol (300 mg, 1.28 mmol) were dissolved in 15 mL of dry DMF under dry nitrogen, topped with a reflux condenser. The reaction mixture was heated to 130° C. for 24 h. After cooling the mixture was added to 50 mL of saturated po... | O=Cc1ccccc1Sc1ccc2ccc3cccc4ccc1c2c34 | null | 46.2 | null |
164,122 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH3:19])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[C:20](OC(=O)C)(=[O:22])C>C(O)=O>[CH:20]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH3:19])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)=[O:22] | CC(=O)OC(C)=O | CCOCCON=C(C(=O)OCC)c1csc(N)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | null | null | Ethyl 2-(2-aminothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetate (syn isomer, 11.5 g.), acetic anhydride (8.2 g.) and formic acid (3.7 g.) were treated in a similar manner to that of Example A-(4) to give ethyl 2-(2-formamidothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetate (syn isomer, 8.6 g.). | CCOCCON=C(C(=O)OCC)c1csc(NC=O)n1 | null | 68.1 | null |
330,175 | ord_dataset-2c460e2ef9934444aaf26fec1f75741f | null | 1996-01-01T00:05:00 | true | [OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH:9]2[C:12]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13]2)=[CH:4][C:3]=1[O:25][CH3:26].C=O.[C:29]([BH3-])#N.[Na+].[BrH:33]>CC(O)C.CO>[BrH:33].[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH3:29])[CH:9]2[C... | COc1cc2c(cc1O)C(C1(c3ccccc3Cl)CC(C)(C)C1)NCC2 | [BH3-]C#N | null | Br | C=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | CO | null | null | null | null | null | null | null | null | null | 5 | 1.5 | A mixture of 7-hydroxy-6-methoxy-[1-(2-chlorophenyl)-3,3-dimethylcyclobutyl]-1,2,3,4-tetrahydroisoquinoline (3.7 g), methanol (50 ml) and 37-40% aqueous formaldehyde solution was cooled to 5° C. Sodium cyanoborohydride (1.4 g) was added and the mixture stirred for 1.5 hours. The solvents were removed by evaporation and... | COc1cc2c(cc1O)C(C1(c3ccccc3Cl)CC(C)(C)C1)N(C)CC2 | null | null | null |
1,682,401 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13](Cl)[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].O.[NH2:17][NH2:18]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([NH:17][NH2:18])[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6] | NN | CC(C)(C)OC(=O)c1cc(Cl)nc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 75 | 18 | To a solution of tert-butyl 2,6-dichloroisonicotinate (11.0 g, 44.3 mmol) in ethanol (222 mL) was added hydrazine hydrate (6.46 mL, 133 mmol). The mixture was heated 75° C. After 18 h, the mixture was cooled to ambient temperature. The mixture was concentrate down to half of the volume. The solid crashed out was filter... | CC(C)(C)OC(=O)c1cc(Cl)nc(NN)c1 | null | null | null |
1,581,351 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | Br[C:2]1[CH:3]=[C:4]([S:12]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([N:22]3[CH:26]=[N:25][N:24]=[CH:23]3)[CH2:17]2)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH2:27]([O:31]C=C)[CH2:28]CC.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:27]([C:2]1[CH:3]=[C:4]([S:12]([NH:15][C@H:... | O=S(=O)(N[C@H]1CCC[C@@H](n2cnnc2)C1)c1cc(Br)cc(C(F)(F)F)c1 | C=COCCCC | null | [Pd+2] | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 80 | 6 | Palladium acetate (9.9 mg, 0.044 mmol) was added to a stirred solution of 3a (100 mg, 0.221 mmol), n-butylvinyl ether (221 mg, 2.206 mmol) and triethylamine (92.0 μL, 0.662 mmol) in DMF (2.00 mL), and the resulting mixture was degassed and heated to 80° C. After 6 h, the reaction mixture was cooled to 0° C., 1M HCl was... | CC(=O)c1cc(C(F)(F)F)cc(S(=O)(=O)N[C@H]2CCC[C@@H](n3cnnc3)C2)c1 | null | null | null |
794,440 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [C:1]([O:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:21][CH:22]=2)=[CH:11][C:10]=1[CH:29]=[O:30])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:1... | CC(C)(C)OC(=O)CCc1ccc(OCCc2coc(-c3ccccc3)n2)cc1C=O | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A 100 mL round bottomed flask was charged with 3-{2-formyl-4-[2-(2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester (1.82 g, 4.18 mmol) and absolute ethanol (20 mL). The stirring solution was cooled in an ice/ethanol bath and treated with sodium borohydride (0.31 g, 8.36 mmol). The cold bath was removed,... | CC(C)(C)OC(=O)CCc1ccc(OCCc2coc(-c3ccccc3)n2)cc1CO | null | null | null |
193,981 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | [H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([F:21])[C:10]=1[C:11](OC)=[O:12]>C(OCC)C>[CH3:7][O:8][C:9]1[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([F:21])[C:10]=1[CH2:11][OH:12] | COC(=O)c1c(F)c(F)cc(F)c1OC | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | Lithium aluminium hydride (1.5 g) was added in portions to a stirred mixture of methyl 2-methoxy-3,5,6-trifluorobenzoate (10.9 g) in dry diethyl ether (80 cm3) over a period of 30 minutes at the ambient temperature and the resultant mixture stirred for a further period of 30 minutes. The product, 2-methoxy-3,5,6-triflu... | COc1c(F)cc(F)c(F)c1CO | null | 92.5 | null |
895,570 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]([CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:26]([O:28][C:29](=[O:33])[CH:30](Br)Br)[CH3:27]>CN(C=O)C>[CH2:26]([O:28][C:29]([CH:30]1[O:16][C:13]2[CH:14]=[CH:15][C:10]([CH2:9][CH:8]([NH:7][C:6... | CC(Cc1ccc(O)c(O)c1)NC(=O)OC(C)(C)C | CCOC(=O)C(Br)Br | 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 | 120 | null | To 1.30 g (4.6 mmol) of 3C was added 40 ml of anhydrous DMF followed by 2.5 g (18 mmol) of anhydrous K2CO3, 2.5 g of 3 A° molecular sieves and 2.3 mL (17.7 mmol) of ethyldibromoacetate. The reaction mixture was heated at 120° C. for 3 hours under argon atmosphere and concentrated under reduced pressure. To the residue ... | CCOC(=O)C1Oc2ccc(CC(C)NC(=O)OC(C)(C)C)cc2O1 | null | 25.4 | null |
1,641,894 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][N:3]=1.[CH:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])OCC>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:10]([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19])=[CH:4][N:3]=1 | O=Cc1ccc(Br)nc1 | CCOC(OCC)OCC | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | In ethanol (60 mL) was dissolved 6-bromonicotinaldehyde (2.00 g, 10.8 mmol). Triethyl orthoformate (5.37 mL, 32.3 mmol) and p-toluenesulfonic acid monohydrate (102 mg, 0.538 mmol) were added and the mixture was refluxed for 2 hours. The solvent in the reaction mixture was evaporated under reduced pressure, and a satura... | CCOC(OCC)c1ccc(Br)nc1 | null | 92.2 | null |
426,926 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | S([O-])([O-])(=O)=O.[Mg+2].[CH:7]1[C:12]([C@@H:13](O)[CH2:14]N)=[CH:11][C:10]([OH:17])=[C:9](O)[CH:8]=1.[C:19]([O:22][CH2:23][CH3:24])(=O)[CH3:20]>[Pt]>[CH2:23]([O:22][C:19]1[CH:20]=[CH:11][C:12]([CH2:7][CH2:8][CH2:9][CH:10]=[O:17])=[CH:13][CH:14]=1)[C:24]1[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1 | NC[C@H](O)c1ccc(O)c(O)c1 | CCOC(C)=O | null | [Pt] | O=S(=O)([O-])[O-] | [Mg+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-(4-benzyloxyphenyl)-butanal (52.4 g, 206 mmol) in 150 mL ethyl acetate (1.4M solution) was prepared and set aside. 10% platinum on carbon (3.40 g) was prewetted with ethyl acetate and transferred to the reactor. To this was added magnesium sulfate (60.0 g, 500 mmol), followed by the ethyl acetate soluti... | O=CCCCc1ccc(OCc2ccccc2)cc1 | null | null | null |
882,324 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:25][CH2:24][C:14]2([O:18][C:17](=[O:19])[NH:16][CH:15]2[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:28]1([CH2:34]Br)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13]... | CCCCC1NC(=O)OC12CCN(C(=O)OCc1ccccc1)CC2 | BrCC1CCCCC1 | null | [H-] | [Na+] | 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 | 70 | 0.08 | To a solution of 5.0 g 4-butyl-2-oxo-1-oxa-3,8-diaza-spiro[4.5]decane-8-carboxylic acid benzyl ester (14.4 mmol) in 50 mL DMF was added 994 mg of sodium hydride (21.6 mmol, 60% dispersion in mineral oil). The reaction mixture stirred for five minutes and 2.2 mL of cyclohexylmethyl bromide (15.8 mmol) was then added. Th... | CCCCC1N(CC2CCCCC2)C(=O)OC12CCN(C(=O)OCc1ccccc1)CC2 | null | 64.3 | null |
881,169 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]3[CH2:25][CH2:24][CH2:23]3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1>O1CCCC1.CO.[C].[Pd]>[NH2:30][C:28]1[CH:27]=[CH:26][C:3]([O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7](... | O=C(Nc1cc(Oc2ccc([N+](=O)[O-])cc2F)ncn1)N1CCN(CCN2CCC2)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | 16.5 | 4-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]amide (110 mg) was dissolved in tetrahydrofuran (3 ml) and methanol (3 ml), and then 10% palladium carbon (53 mg) was added, followed by stirring under a hydrogen atmosphere for 16.5 hrs. The catalyst was filtered off and ... | Nc1ccc(Oc2cc(NC(=O)N3CCN(CCN4CCC4)CC3)ncn2)c(F)c1 | null | 31.6 | null |
286,550 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[CH:10]([NH:12][CH:13]([C:19]([O-])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11].C1(N=C=NC2CCCCC2)CCCCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:19](=[O:20])[CH:13]([NH:12][CH:10]=[O:11])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]([Cl:9])[CH:8]=1 | Nc1cc(Cl)cc(Cl)c1 | CCOC(=O)C(NC=O)C(=O)[O-] | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3,5-Dichloroaniline, mono-ethyl formamidomalonate and 1,3-dicyclohexylcarbodiimide were reacted in a manner similer to that described in Example XCI Part B to give ethyl 3-[(3,5-dichlorophenyl)amino]-2-formamido-3-oxopropanoate having a melting point of 147.0° C.-148.0° C. Elemental analysis of the product indicated th... | CCOC(=O)C(NC=O)C(=O)Nc1cc(Cl)cc(Cl)c1 | null | null | null |
1,745,974 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24](C)[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1I.C([Sn](CCCC)(CCCC)[C:34]1[S:35][CH:36]=[CH:37][N:38]=1)CCC.[Cl-].C(N(CC)CC)C>CN(C)C=O.[Cu]I>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4... | CCCC[Sn](CCCC)(CCCC)c1nccs1 | Cc1ccn2nc([C@H](C)Nc3ncnc(N)c3I)n(-c3ccccc3)c(=O)c12 | null | [Cu]I | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 60 mg (0.07 mmol) of (S)-2-(1-((6-amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one, 43 mg (0.11 mmol) of 2-(tributylstannyl)thiazole, 2.0 mg (0.01 mmol) of bis-triphenylphosphinepalladium(II) chloride, 4.4 mg (0.02 mmol) of copper (I) iodide and 32 μl (0.23 mmol) of trieth... | C[C@H](Nc1ncnc(N)c1-c1nccs1)c1nn2cccc2c(=O)n1-c1ccccc1 | null | 13.3 | null |
838,595 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | C[O:2][C:3]([C:5]1([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[K+]>CS(C)=O.O>[F:16][C:14]1[CH:15]=[C:10]([C:5]2([C:3]([OH:4])=[O:2])[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:11]=[C:12]([F:17])[CH:13]=1 | COC(=O)C1(c2cc(F)cc(F)c2)CCCC1 | null | null | [K+] | [OH-] | 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 | 25 | 2.5 | To a solution of 1-(3,5-difluorophenyl)cyclopentanecarboxylic acid methyl ester (Step A, 2.0 g, 8.3 mmol) in dimethylsulfoxide (5 mL) was added potassium hydroxide (1.9 g, 33 mol) in 2 mL of water. After stirring at room temperature for 2.5 h, the reaction mixture was partitioned between ether (50 mL) and saturated aqu... | O=C(O)C1(c2cc(F)cc(F)c2)CCCC1 | null | null | null |
1,074,014 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=2)[CH:7]=1.[N:14]1([C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][NH:26][CH2:27]3)=[CH:22][CH:21]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([N:26]3[CH2:25][CH2:24][C:23]4[C:28](=[CH:29][C:20]... | c1cc2c(cc1N1CCOCC1)CNCC2 | O=C(O)c1cc2ncc(Br)cn2n1 | null | null | null | null | null | null | null | 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 close analogy to the procedure described in Example 1, 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid is reacted with 7-Morpholin-4-yl-1,2,3,4-tetrahydro-isoquinoline to provide the title compound in moderate yield. | O=C(c1cc2ncc(Br)cn2n1)N1CCc2ccc(N3CCOCC3)cc2C1 | null | null | null |
1,323,691 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH2:1]([C:5]1=[CH:6][N:7]([C:24]([CH3:27])([CH3:26])[CH3:25])[S:8]/[C:9]/1=[N:10]\[C:11]([C@:13]1([CH3:23])[CH2:17][CH2:16][C@H:15]([C:18](O)=[O:19])[C:14]1([CH3:22])[CH3:21])=[O:12])[CH2:2][CH2:3][CH3:4].Cl.[CH2:29]([NH2:31])[CH3:30]>>[CH2:1]([C:5]1=[CH:6][N:7]([C:24]([CH3:27])([CH3:25])[CH3:26])[S:8]/[C:9]/1=[N:10]\... | CCN | CCCCc1cn(C(C)(C)C)s/c1=N\C(=O)[C@]1(C)CC[C@H](C(=O)O)C1(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 product from Example 173 and ethylamine hydrochloride (Aldrich) were processed using the method described in Example 178 to afford the title compound. 1H NMR (DMSO-d6) δ 0.48 (s, 3H), 0.90 (t, J=7.0 Hz, 3H), 1.00 (t, J=7.2 Hz, 3H), 1.23 (2, 3H), 1.19 (s, 3H), 1.26-1.44 (m, 3H), 1.57 (s, 9H), 1.57-1.70 (m, 3H), 1.96... | CCCCc1cn(C(C)(C)C)s/c1=N\C(=O)[C@]1(C)CC[C@H](C(=O)NCC)C1(C)C | null | null | null |
1,375,689 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [C:1]([O:5][CH:6]([C:11]1[C:12]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[O:27][CH2:26][CH2:25][CH2:24]3)=[C:13]2[CH:20]=[CH:19][NH:18][C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]1[CH:39]=[C:38]([F:40])[CH:37]=[C:36]([F:41])[C:33]=1[CH2:34]Br>>[C:1]([O:5][CH:6]([C:11]1... | COC(=O)C(OC(C)(C)C)c1c(C)nc2[nH]ccc2c1-c1ccc2c(c1)CCCO2 | Fc1cc(F)c(CBr)c(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a manner similar to that described in Example 27, Step H from methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate and 2,4,6-trifluorobenzyl bromide. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.41 (s, 1 H), 7.20 (d, J=10.0 Hz, 1 H), 7.08 (t, J=4.0 Hz, 1... | Cc1nc2c(ccn2Cc2c(F)cc(F)cc2F)c(-c2ccc3c(c2)CCCO3)c1C(OC(C)(C)C)C(=O)O | null | null | null |
1,512,618 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:5]2=[N:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1 | OCc1ccn2c(I)cnc2c1 | null | null | O=[Ru](=O)(=O)[O-] | CCC[N+](CCC)(CCC)CCC | C[N+]1([O-])CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of (3-Iodo-imidazo[1,2-a]pyridin-7-yl)methanol (1.00 g, 3.65 mmol) and NMO (0.64 g, 5.47 mmol) in CH2Cl2 (30 ml) with sieves (3 g) at 0° C. was added TPAP (0.06 g, 0.18 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 18 h, before being filtered to remove the sieves. The... | O=Cc1ccn2c(I)cnc2c1 | null | 15.1 | null |
804,268 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:9]=2)[C:4](=[O:19])[CH2:3]1.[C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)#[N:22]>>[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:27]3[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=3)[C:21]#[N:22])[CH:9]=2)[C:4](=[O:19])[CH2... | CC1(C)CC(=O)c2ccc(OS(=O)(=O)C(F)(F)F)cc21 | N#Cc1cccc(B(O)O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from trifluoro-methanesulfonic acid 3,3-dimethyl-1-oxo-indan-5-yl ester and 3-cyanophenyl boronic acid according to the procedure described in example 21. MS (ESI) m/z 262; HRMS: calcd for C18H15NO+H+, 262.12264; found (ESI, [M+H]+), 262.1219. | CC1(C)CC(=O)c2ccc(-c3cccc(C#N)c3)cc21 | null | null | null |
1,003,428 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)=O.[C:19]([O:23][C:24](=[O:36])[CH2:25][CH2:26][N:27]([CH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[C:28]([NH2:30])=[S:29])([CH3:22])([CH3:21])[CH3:20]>CN1C(=O)CCC1>[C:19]([O:23][C:24](=[O:36])[CH2:2... | C[C@H]1CC[C@H](Oc2ccc(C(=O)CBr)cc2)CC1 | CC(C)(C)OC(=O)CCN(C(N)=S)C1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | The 2-bromo-1-[4-(trans-4-methyl-cyclohexyloxy)-phenyl]-ethanone (764 mg, 3.44 mmol), 3-(1-cyclopentyl-thioureido)-propionic acid tert-butyl ester (935 mg, 2.46 mmol), NMP (6 mL) were combined as indicated in general procedure B. The reaction was stirred at room temperature overnight. After an aqueous work up, the crud... | CC(C)(C)OC(=O)CCN(c1nc(-c2ccc(O[C@H]3CC[C@H](C)CC3)cc2)cs1)C1CCCC1 | null | null | null |
821,423 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:21])[C@@H:12]([NH2:20])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4].[C:22]([O:26][C:27]([NH:29][C@H:30]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:31](O)=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(C(C)C)CC)(C)C.ON1C2C=CC=CC... | CC(C)(C)OC(=O)N[C@@H](C(=O)O)c1ccccc1 | COC(=O)c1csc(NC(=O)[C@@H](N)Cc2ccccc2)n1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0.08 | A solution of 2-((S)-2-amino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (prepared as described in example 3, step c) (0.61 g, 2.0 mmol), (R)-tert-butoxycarbonylamino-phenylacetic acid (0.55 g, 2.2 mmol), diisopropylethylamine (1.40 mL, 7.88 mmol) and 1-hydroxybenzotriazole (0.324 g, 2.40 mmol) in ... | COC(=O)c1csc(NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](NC(=O)OC(C)(C)C)c2ccccc2)n1 | null | null | null |
1,654,213 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[OH:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1.[O:30]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31]1>C(Cl)Cl>[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])... | C1=COCCC1 | CCOC(=O)C1CCC(O)CC1 | null | Cc1ccc(S(=O)(=O)[O-])cc1 | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | Pyridinium-4-toluenesulfonate (2.57 g, 10.2 mmol) was added to a solution of ethyl 4-hydroxycyclohexanecarboxylate (8.8 g, 51.10 mmol) and 3,4-dihydro-2H-pyran (8.60 g, 102 mmol) in DCM (200 mL). After 16 hours the reaction was quenched with saturated aqueous sodium bicarbonate. The layers were separated and the organi... | CCOC(=O)C1CCC(OC2CCCCO2)CC1 | null | null | null |
1,322,887 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Cl[C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][CH2:9][C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15]([Cl:21])=[CH:16][CH:17]=3)[N:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=2)=[O:7])=[CH:4][N:3]=1.Cl.[CH3:31][S:32]([CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)(=[O:34])=[O:33]>>[Cl:21][C:15]1[CH:14]=[C... | O=C(NCc1cn(-c2ccccc2)c2cc(Cl)ccc2c1=O)c1ccc(Cl)nc1 | CS(=O)(=O)C1CCNCC1 | 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-Methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide was prepared starting from intermediate E and 4-methanesulfonyl piperidine hydrochloride. MS calcd. for C28H27ClN4O4S [(M+H)+] 551.1, obsd. 551. | CS(=O)(=O)C1CCN(c2ccc(C(=O)NCc3cn(-c4ccccc4)c4cc(Cl)ccc4c3=O)cn2)CC1 | null | null | null |
557,756 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:6][C:5]=1[N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])([O-])=O>[Pd].C1(C)C=CC=CC=1.CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:1... | CN(C(=O)OC(C)(C)C)c1cc(Oc2ccc(Oc3ccccc3)cc2)ccc1[N+](=O)[O-] | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | In a similar manner to that described in Reference Example 7, a reaction was carried out using t-butyl N-[2-nitro-5-(4-phenoxyphenoxy)phenyl]-N-methylcarbamate (8.6 g), palladium on carbon (10%, 0.6 g) and toluene/methanol=16/3 (190 ml) and the reaction mixture was purified to give the title compound (7.2 g). | CN(C(=O)OC(C)(C)C)c1cc(Oc2ccc(Oc3ccccc3)cc2)ccc1N | null | 89.9 | null |
1,328,296 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([O:18][C:19](=[O:25])[NH:20][CH:21]1[CH2:24][NH:23][CH2:22]1)([CH3:17])([CH3:16])[CH3:15]>>[C:14]([O:18][C:19](=[O:25])[NH:20][CH:21]1[CH2:24][N:23]([CH:10]2[CH2:11][CH2:12][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[... | O=C1CCC(c2ccccc2)CC1 | CC(C)(C)OC(=O)NC1CNC1 | null | null | null | null | null | null | null | 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 as a white solid by reductive amination of 4-phenyl-cyclohexanone and azetidin-3-yl-carbamic acid tert-butyl ester using the procedure described in Step D of Example 1. | CC(C)(C)OC(=O)NC1CN(C2CCC(c3ccccc3)CC2)C1 | null | null | null |
1,523,831 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[CH3:16][C:17]1[CH:21]=[C:20]([NH2:22])[N:19]([C:23]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:24]=2[CH:25]=[CH:26][CH:27]=[N:28]3)[N:18]=1.ClCCl>N1C=CC=CC=1>[CH3:16][C:17]1[CH:21]=[C:20]([NH:22][S:12]([C:9]2[CH:10]=[CH:... | CCC(C)(C)c1ccc(S(=O)(=O)Cl)cc1 | Cc1cc(N)n(-c2cccc3ncccc23)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of 4-t-pentylbenzenesulfonyl chloride (0.13 g, 0.53 mmol) and 3-methyl-1-(quinolin-5-yl)-1H-pyrazol-5-amine (prepared from Example 4 step b, 0.10 g, 0.44 mmol) in pyridine (1.0 mL) was heated at 80° C. for 3 h with stirring. After cooling to room temperature, dichloromethane was added to the reaction mixture ... | CCC(C)(C)c1ccc(S(=O)(=O)Nc2cc(C)nn2-c2cccc3ncccc23)cc1 | null | 54.5 | null |
80,834 | ord_dataset-f196f0a87dd74fcd82ca019f8ff5cf9c | null | 1981-01-01T00:05:00 | true | [CH2:1]([S:3][C:4]1[C@:5]2([CH2:22][C@H:21]([OH:23])[C@@:20]3([F:24])[C@@H:10]([CH2:11][CH2:12][C:13]4[C@:18]3([CH3:19])[CH:17]=[CH:16][C:15](=[O:25])[CH:14]=4)[C@@H:7]2[CH2:8][CH:9]=1)[CH3:6])[CH3:2].[Br:26]N1C(=O)CCC1=O>ClCCl>[Br:26][C:9]1[CH2:8][C@H:7]2[C@H:10]3[C@:20]([F:24])([C@@H:21]([OH:23])[CH2:22][C@:5]2([CH3:... | O=C1CCC(=O)N1Br | CCSC1=CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of (11β)-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one (181 mg) in dichloromethane (10 ml) containing N-bromosuccinimide (98 mg) is stirred at room temperature for 2 hours and the reaction mixture is subjected to preparative thin layer chromatography on silica gel plates to isolate the title ... | CCSC1=C(Br)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C | null | null | null |
1,138,984 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]2)=[O:10])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].C=O.[C:22]([BH3-])#N.[Na+].O>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[CH3:22])=[O:10])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18] | Nc1ccc(NC(=O)[C@H]2CCCCN2)cc1[N+](=O)[O-] | [BH3-]C#N | null | C=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 1.17 | (R)—N-(4-Amino-3-nitrophenyl)piperidine-2-carboxamide (2.09 g, 7.9 mmol) was dissolved in MeOH (50 mL), and paraformaldehyde (0.95 g) and sodium cyanoborohydride (0.50 g, 8.0 mmol) were added. The mixture was stirred at room temperature for 70 min, and water added dropwise. The solvent was evaporated and the residue pa... | CN1CCCC[C@@H]1C(=O)Nc1ccc(N)c([N+](=O)[O-])c1 | null | 98.7 | null |
1,488,733 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | Cl[C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:12][Si:11]([CH3:14])([CH3:13])[CH... | C[Si](C)(C)CCOCn1c(Cl)nc2ccccc21 | CC(C)(C)OC(=O)Nc1ccc(O)cc1 | null | O=C([O-])[O-] | [Cs+] | 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 | 60 | 24 | A mixture of 2-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole (8.7 g), tert-butyl 4-hydroxyphenylcarbamate (6.4 g) and cesium carbonate (20 g) in DMF (60 mL) was stirred at 60° C. for 24 h. After cooling to room temperature, to the mixture was added SiO2, the mixture was evaporated, and then the residue w... | CC(C)(C)OC(=O)Nc1ccc(Oc2nc3ccccc3n2COCC[Si](C)(C)C)cc1 | null | 100.5 | null |
1,170,581 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(O)(=O)C.[C:26]([O:30][C:31](=[O:37])[N:32]([CH3:36])[CH2:33][CH:34]=O)([CH3:29])([CH3:28])[CH3:27].C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO>[C:26]([O:30][C:31]... | Nc1ccc2nc(N[C@@H]3CCc4ccccc43)ccc2c1 | CN(CC=O)C(=O)OC(C)(C)C | null | O=C([O-])O | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC(=O)O | null | null | null | null | null | null | null | null | null | 23 | 1 | A mixture of (R)—N2-indan-1-yl-quinoline-2,6-diamine (453 mg, 1.645 mmol) in Methanol (10 mL) with acetic acid (0.3 mL, 4.935 mmol) and commercially available methyl-(2-oxo-ethyl)carbamic acid tert-butyl ester (300 mg, 1.731 mmol) was stirred at 23° C. for 1 h. Portionwise addition of sodium cyanoborohydride (286 mg, 4... | CN(CCNc1ccc2nc(N[C@@H]3CCc4ccccc43)ccc2c1)C(=O)OC(C)(C)C | null | 77.3 | null |
1,390,024 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])C.[Li+].[OH-]>CCO>[C:9]1([C@@H:7]2[CH2:8][C@H:6]2[C:4]([OH:5])=[O:3])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1 | CCOC(=O)[C@@H]1C[C@H]1c1ccccc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a stirred mixture of 33 (153 g, 804.25 mmol, 1.00 equiv) in EtOH (1 L) was added 1M aq. LiOH (1 L), and the resultant solution was stirred at reflux for 1 h. Volatile solvent was removed under reduced pressure and the residue diluted with EtOAc (1.5 L). The organic phase was washed with water (3×1 L) and brine (1×1 ... | O=C(O)[C@@H]1C[C@H]1c1ccccc1 | null | 90.1 | null |
1,577,133 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:14][O:13]1.[CH3:15][CH:16]1[CH2:21][NH:20][CH2:19][CH2:18][NH:17]1>CS(C)=O.O>[CH3:15][CH:16]1[CH2:21][N:20]([CH2:14][CH:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[CH3:1])[OH:13])[CH2:19][CH2:18][N:17]1[CH2:... | CC1CNCCN1 | Cc1c(C2CO2)ccc2c1COC2=O | null | null | null | 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 | 150 | null | A mixture of 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one (700 mg, 3.684 mmol) and 2-methylpiperazine (184 mg, 1.842 mmol) in 2 mL DMSO was heated under microwave condition (150° C.) for 1 hr. After cooling to rt., the mixture was diluted with water (50 mL), extracted with EtOAc (3×50 mL). The combined organic layers ... | Cc1c(C(O)CN2CCN(CC(O)c3ccc4c(c3C)COC4=O)C(C)C2)ccc2c1COC2=O | null | null | null |
930,380 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | C([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[C:29]([F:37])[CH:28]=4)[CH:24]=[C:23]([C:38]([F:41])([F:40])[F:39])[N:22]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:37][C:2... | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(-c3nc(-c4ccc(C(F)(F)F)c(F)c4)cc(C(F)(F)F)n3)c2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 15 | To a cooled and stirred solution of 3′-[4-(3-fluoro-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide (0.47 g) in dichloromethane (6 ml) was added TFA (6 ml) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to drynes... | NS(=O)(=O)c1cccc(-c2cccc(-c3nc(-c4ccc(C(F)(F)F)c(F)c4)cc(C(F)(F)F)n3)c2)c1 | null | 63.4 | null |
656,209 | ord_dataset-f5d908a6dcb44353a706166b5e9f7f88 | null | 2004-01-01T00:12:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2(O)[CH2:14][N:13]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CS([Cl:33])(=O)=O>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([Cl:33])[CH2:14][N:13]([CH:15]([C:22]3[CH:27]... | CS(=O)(=O)Cl | CC(C)(C)c1ccc(C2(O)CN(C(c3ccccc3)c3ccccc3)C2)cc1 | 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 | 18 | To a stirred solution of compound (9) (6.23 g) and N,Ndiisopropylethylamine (3.5 mL) in dichloromethane (100 mL) at 0° C. was added, dropwise, methanesulfonyl chloride (1.4 mL). The mixture was stired at 0° C. for 18 hrs, then washed (water, brine), dried (Na2SO4) and concentrated in vacuo. The crude product was recrys... | CC(C)(C)c1ccc(C2(Cl)CN(C(c3ccccc3)c3ccccc3)C2)cc1 | null | null | null |
900,868 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH3:10])[CH:3]=1.[Li]CCCC.C[O:17][B:18](OC)[O:19]C>C1COCC1>[CH2:8]([C:4]1[CH:3]=[C:2]([B:18]([OH:19])[OH:17])[CH:7]=[CH:6][CH:5]=1)[CH2:9][CH3:10] | COB(OC)OC | CCCc1cccc(Br)c1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 0.08 | To a solution of Intermediate 214.1 (130 mg, 0.65 mmol) in 4 mL THF at −78° C., was added BuLi (1.4 M in hexanes, 0.557 mL, 0.78 mmol). The mixture was stirred 5 min at −78° C., then trimethylborate (0.109 mL, 0.975 mmol) was added. The reaction was stirred at −78° C. for 10 min, then was removed from the cooling bath ... | CCCc1cccc(B(O)O)c1 | null | 77.9 | null |
361,027 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [Br:1][CH:2]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:5]=2[NH:4][C:3]1=[O:20].[CH3:21][C:22]1([NH:28][C:29](=[O:32])[CH2:30]I)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:21][C:22]1([NH:28][C:29](=[O:32])[CH2:30][N:4]2[C:5]3[CH:18]=[C:17]([CH3:19])[C... | Cc1ccc2c(c1)NC(=O)C(Br)CC2c1ccccc1 | CC1(NC(=O)CI)CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared as in Example 20I from 3-bromo-5-phenyl-8-methyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one using N-(1-methylcyclohexyl)-iodoacetamide, M.P. x° C., x% yield for the trans isomer. | Cc1ccc2c(c1)N(CC(=O)NC1(C)CCCCC1)C(=O)C(Br)CC2c1ccccc1 | null | null | null |
1,421,611 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | Cl[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][NH2:14]>>[NH:13]([C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[NH2:14] | NN | Cc1cc(Cl)nc2ncccc12 | null | null | null | null | null | 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 | A solution of 2-chloro-4-methyl-1,8-naphthyridine (330 mg, 1.8 mmol) in NH2NH2 was refluxed at 130° C. for 2 hours. The reaction mixture was cooled to room temperature, then excess NH2NH2 was removed on the rotary evaporator. The residue was taken up in 20 mL of CH2Cl2. The mixture was washed with saturated NaHCO3 (3×1... | Cc1cc(NN)nc2ncccc12 | null | null | null |
1,476,149 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [NH2:1][C:2]1[C:3]([C:13]([O:15]C)=[O:14])=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:6][CH:7]=1.[Li+].[OH-].Cl>C1COCC1>[NH2:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:6][CH:7]=1 | COC(=O)c1nc(-c2nccs2)ccc1N | null | null | Cl | [Li+] | [OH-] | 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 | 60 | 4 | To a solution of methyl 3-amino-6-(thiazol-2-yl)picolinate (1.0 equiv) in THF (0.5M), was added 1M LiOH (4.0 equiv). After stirring for 4 hours at 60° C., 1 N HCl (4.0 equiv.) was added and the THF was removed in vacuo. The resulting solid was filtered and rinsed with cold H2O (3×20 mL) to yield 3-amino-6-(thiazol-2-yl... | Nc1ccc(-c2nccs2)nc1C(=O)O | null | 61 | null |
1,333,889 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.C(N(CC)CC)C.[O:26]=[C:27]([C:31]1[N:39]2[C:34]([CH2:35][CH2:36][CH2:37][CH2:38]2)=[CH:33][C:32]=1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:28](Cl)=[O:29]>C(Cl)Cl>[CH3:1][C:2](... | O=C(Cl)C(=O)c1c(-c2ccccc2)cc2n1CCCC2 | CC(C)(C)CN1CCN(c2ccc(N)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To an ice-cold solution of 4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenylamine (prepared as described in Reference Example 93, 300 mg, 1.21 mmol) and triethylamine (0.33 mL, 2.4 mmol) in dry DCM (12 mL) was added a solution of oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride (prepared as described in... | CC(C)(C)CN1CCN(c2ccc(NC(=O)C(=O)c3c(-c4ccccc4)cc4n3CCCC4)cc2)CC1 | null | 36.5 | null |
623,825 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[O:8][C:9]([CH3:28])=[C:10]([CH3:27])[C:11]=2[C:12]([C:14]2[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([OH:23])=[C:16]([CH:24]([CH3:26])[CH3:25])[CH:15]=2)=[O:13])=[CH:4][CH:3]=1.Cl[S:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[C:37]([OH:44])[CH:36]=1)(=[O... | Cc1oc(Cc2ccc(Br)cc2)c(C(=O)c2cc(C(C)C)c(O)c(C(C)C)c2)c1C | O=C(O)c1ccc(S(=O)(=O)Cl)cc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the procedure in Example 4 using [2-(4-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone (1.30 g, 2.77 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (1.00 g, 4.22 mmol). Purification on Dynamax C18 (90% CH3CN/H20) gave 0.98 g (53%) of th... | Cc1oc(Cc2ccc(Br)cc2)c(C(=O)c2cc(C(C)C)c(OS(=O)(=O)c3ccc(C(=O)O)c(O)c3)c(C(C)C)c2)c1C | null | 52.8 | null |
1,305,166 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:33])[C:18]([NH:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:41][CH2:42][C:43](Cl)=[O:44]>C(Cl)Cl>[C:1]1([S:7]([N:... | O=C(Cl)CCl | Nc1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1NC1CCN(Cc2ccccc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 2 | To an ice-cold mixture of 1-benzenesulfonyl-N*4*-(1-benzyl-piperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine 1.30 g, 2.80 mmol) and triethylamine (0.59 mL, 4.20 mmol) in DCM (50 mL) was added chloroacetyl chloride (0.25 mL, 3.10 mmol) and the mixture was stirred 2 h. The reaction mixture was diluted with DCM, washe... | O=C(CCl)Nc1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1NC1CCN(Cc2ccccc2)CC1 | null | 73 | null |
1,184,105 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6]2.[OH-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6]2 | COc1ccc2ncc([N+](=O)[O-])cc2c1 | null | null | Br | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 120 | 16 | 6-Methoxy-3-nitroquinoline (Magnus, P. et al., J. Am. Chem. Soc. 119, 5591, 1997; 100 mg, 0.49 mmol) was dissolved in hydrogen bromide solution (47% aq, 2.5 mL, 0.2 M), heated and stirred at 120° C. for 16 hours. The reaction mixture was cooled to room temperature, neutralized with 6N NaOH, then extracted with EtOAc (1... | O=[N+]([O-])c1cnc2ccc(O)cc2c1 | null | 78.3 | null |
412,751 | ord_dataset-fbdd058349aa456f812e3546c84baab5 | null | 1998-01-01T00:09:00 | true | C([S:4][CH2:5][CH:6]([CH2:10][C:11]([OH:13])=[O:12])[C:7]([OH:9])=[O:8])(=O)C.[OH-].[Na+]>O>[SH:4][CH2:5][CH:6]([CH2:10][C:11]([OH:13])=[O:12])[C:7]([OH:9])=[O:8] | CC(=O)SCC(CC(=O)O)C(=O)O | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 15 | 582 g (2.85 mol) of acetylthiomethylbutanedioic acid (VII) are added, under nitrogen and while cooling with ice, to a solution of 570 g (14.25 mol) of NaOH in 3 litres of water (exothermic reaction). After 15 hours' stirring at room temperature, the reaction mixture is acidified to pH 1 with concentrated hydrochloric a... | O=C(O)CC(CS)C(=O)O | null | 82.3 | null |
1,752,016 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][N:17]=1)=O.P(Cl)(Cl)(Cl)(Cl)[Cl:27]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[N:13]=[C:14]([Cl:27])[C:16]1[C... | ClP(Cl)(Cl)(Cl)Cl | CS(=O)(=O)c1ccc(C(=O)Nc2ccc(OC(F)(F)F)cc2Cl)nc1 | 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 | 5-Methanesulfonyl-pyridine-2-carboxylic acid (2-chloro-4-trifluoromethoxy-phenyl)-amide 7 (1.1 g, 2.79 mmol) in benzene (20 mL) was added to PCl5 (1.26 g, 6.0 mmol) and the mixture was heated to reflux overnight. The solvent was removed and the residue was further dried under high vacuum. Crude N-(2-chloro-4-trifluorom... | CS(=O)(=O)c1ccc(C(Cl)=Nc2ccc(OC(F)(F)F)cc2Cl)nc1 | null | null | null |
936,911 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1>>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:16][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[N:6][CH:7]=1 | Clc1ncc(Br)cn1 | COc1ccc(CN)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 | 2 | 5-Bromo-2-chloropyrimidine (300 mg, 1.55 mmol) was dissolved by heating at 120° C. in 4-methoxybenzylamine (2.10 g, 15.4 mmol), and the solution was stirred at the same temperature for 2 hours. The reaction mixture was directly subjected to silica gel column chromatography (hexane:ethyl acetate=30:1→5:1) for purificati... | COc1ccc(CNc2ncc(Br)cn2)cc1 | null | 97.6 | null |
587,430 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | [CH:1]1([CH2:6][CH2:7][C:8]2[N:16]([C:17]3[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][NH2:23])=[CH:19][CH:18]=3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:26]1[CH2:28][C@H:27]1[CH2:29][O:30][C:31]1[C:39]2[NH:38][C:37](=[O:40])[NH:36][C:35]=2[CH:34]=[CH:33][CH:32]=1>C(Cl)(Cl)Cl.CO>[C... | NCCc1ccc(-n2c(CCC3CCCC3)nc3cccnc32)cc1 | O=c1[nH]c2cccc(OC[C@@H]3CO3)c2[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 4-[2-(2-Cyclopentylethyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenethylamine (0.229 g, 0.68 mmol) was reacted with 4-[(2S)oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-one (0.141 g, 0.68 mmol) according to Procedure G (eluant: 20:1 going to 5:1 chloroform-methanol containing 1% ammonium hydroxide) to give the title compound... | O=c1[nH]c2cccc(OCC(O)CNCCc3ccc(-n4c(CCC5CCCC5)nc5cccnc54)cc3)c2[nH]1 | null | 8.7 | null |
291,797 | ord_dataset-6c3ec086c8c9475e8d31a44641b49e02 | null | 1994-01-01T00:06:00 | true | [CH:1]1([CH2:4][N:5]2[C:14](=[O:15])[C:13]3[N:12](CCC(=O)C)[CH:11]=[N:10][C:9]=3[N:8]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:6]2=[O:7])[CH2:3][CH2:2]1.[OH-].[K+]>C(O)C>[CH:1]1([CH2:4][N:5]2[C:14](=[O:15])[C:13]3[NH:12][CH:11]=[N:10][C:9]=3[N:8]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:... | CC(=O)CCn1cnc2c1c(=O)n(CC1CC1)c(=O)n2CC1CCCCC1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | This was prepared from the compound of Example 21, 900 mg, by treating with 200 mg potassium hydroxide in 10 ml of ethanol for 1 hour at room temperature. The title compound was isolated in an analogous manner to Example 18, m.p. 181° C. | O=c1c2[nH]cnc2n(CC2CCCCC2)c(=O)n1CC1CC1 | null | null | null |
1,193,241 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19]Br)[CH:6]=1.[Cl:22][C:23]1[CH:36]=[CH:35][C:26]([O:27][C@H:28]2[O:32][C:31](=[O:33])[NH:30][C@@H:29]2[CH3:34])=[CH:25][CH:24]=1>>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8... | COC(=O)Cc1cccc(Oc2ccc(Br)cc2CBr)c1 | C[C@H]1NC(=O)O[C@@H]1Oc1ccc(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 | Prepared according to the procedure described in Example 6, Step 5, using the following starting materials: [3-(4-bromo-2-bromomethyl-phenoxy)-phenyl]-acetic acid methyl ester and (4R,5S)-5-(4-chloro-phenoxy)-4-methyl-oxazolidin-2-one. | COC(=O)Cc1cccc(Oc2ccc(Br)cc2CN2C(=O)O[C@H](Oc3ccc(Cl)cc3)[C@H]2C)c1 | null | null | null |
1,113,242 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [C:1]([CH2:3][N:4]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]#[N:11])[CH:5]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:2].[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>>[CH:20](=[N:11][CH2:10][CH2:9][N:6]1[CH2:7][CH2:8][N:4]([CH2:3][CH2:1][N:2]=[CH:22][C:18]2[CH:16]=[CH:15][CH:14]=[CH:20][CH:19]=2)[CH:5]1[C:12]1[CH:17]=[CH:16][CH... | C1CCOC1 | N#CCN1CCN(CC#N)C1c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 40 | null | 1 equal mole of (3-cyanomethyl-2-phenyl-imidazolidin-1-yl) -acetonitrile and THF were mixed in a reactor and the reactor was purged with nitrogen gas. The reaction mixture was then transferred to a feeding vessel. The reactor was washed with THF and the solution was added into the mixture in the feeding vessel. 3 equal... | C(=NCCN1CCN(CCN=Cc2ccccc2)C1c1ccccc1)c1ccccc1 | null | 84.85 | null |
936,079 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Br:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[N:15]... | BrCC1CCCCC1 | CC(C)(C)OC(=O)N1CCC(C(=O)Nc2ccccc2Br)CC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 1 | 4-(2-Bromo-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 2.60 mmol) was dissolved in dry N,N-dimethylformamide (10.0 mL). To the reaction mixture was then added at 0° C. sodium hydride (60% in mineral oil, 127.3 mg, 3.18 mmol) under nitrogen atmosphere and the reaction mixture was stirred at 0°... | CC(C)(C)OC(=O)N1CCC(C(=O)N(CC2CCCCC2)c2ccccc2Br)CC1 | null | null | null |
1,229,407 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].C(OCC)(=O)C.[BrH:25]>C(O)(=O)C.[Cu](Cl)Cl>[Br:25][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6] | Br | COC(=O)c1ccc(C(=O)O)cc1N | null | Cl[Cu]Cl | O=N[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 0.5 | To 3-amino-4-methoxycarbonylbenzoic acid (1.95 g, 10 mmol) suspended in 48% hydrobromic acid (50 mL) and acetic acid (50 mL), an aqueous solution (20 mL) of sodium nitrite (0.69 g, 10 mmol) was added at −10° C., and the resulting solution was stirred for 30 minutes. The solution was added to copper bromide (I) (1.44 g,... | COC(=O)c1ccc(C(=O)O)cc1Br | null | 59 | null |
860,384 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | Cl[C:2]1[C:3]2[CH:17]=[CH:16][C:15](=[O:18])[N:14]([C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=3[F:26])[C:4]=2[N:5]=[C:6]([NH:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])[N:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[OH:41])O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC... | O=c1ccc2c(Cl)nc(NC(CO)CO)nc2n1-c1c(F)cccc1F | CC1(C)OB(c2ccccc2O)OC1(C)C | 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 | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 150 | null | A solution of 4-Chloro-2-(2-hydroxy-1-hydroxymethyl-ethylamino)-8-(2,6-difluoro-phenyl)-8H-pyrido[2,3-d]pyrimidin-7-one (50 mg, 0.13 mmol) in dioxane/H2O (3:1, 4.8 mL) was mixed with 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (44.0 mg, 0.20 mmol) and K2CO3 (71.9 mg, 0.52 mmol). The resultant mixture was bubb... | O=c1ccc2c(-c3ccccc3O)nc(NC(CO)CO)nc2n1-c1c(F)cccc1F | null | 82 | null |
731,393 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [CH2:1]([C:8]1[C:13](I)=[CH:12][CH:11]=[C:10]([N:15]2[CH2:19][C@@H:18]([O:20][CH3:21])[C@H:17]([OH:22])[CH2:16]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([C:25]1([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)#[CH:24]>>[CH2:1]([C:8]1[C:13]([C:24]#[C:23][C:25]2(... | C#CC1(N2CCCCC2)CCCCC1 | CO[C@@H]1CN(c2ccc(I)c(Cc3ccccc3)n2)C[C@H]1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This was synthesized in the same manner as in Example 6 except that 2-benzyl-3-iodo-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine (Production Example 1) and 1-(1-ethynylcyclohexyl)piperidine (Production Example 18) were used. | CO[C@@H]1CN(c2ccc(C#CC3(N4CCCCC4)CCCCC3)c(Cc3ccccc3)n2)C[C@H]1O | null | null | null |
910,366 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH2:1]([CH:8]1[NH:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][N:32]=[C:33]=[O:34]>ClCCl>[CH3:31][NH:32][C:33]([N:13]1[CH2:12][CH2:11][N:10]([CH2:14][... | CN=C=O | FC(F)(F)c1ccccc1-c1ccc(CN2CCNC(Cc3ccccc3)C2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | This compound could be made in the following manner: 100 mg of 3-benzyl-1-(2′-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine would be dissolved in dichloromethane, 1.1 equiv. methylisocyanate would be added. The reaction would be shaken at room temperature overnight. The reaction would be concentrated in vacuo. The re... | CNC(=O)N1CCN(Cc2ccc(-c3ccccc3C(F)(F)F)cc2)CC1Cc1ccccc1 | null | null | null |
667,435 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | B(Br)(Br)Br.[Cl:5][C:6]1[C:16]([Cl:17])=[C:15]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25]C)[CH:14]=[CH:13][C:7]=1[CH:8]=[CH:9][C:10]([OH:12])=[O:11]>C(Cl)Cl>[OH:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[S:18][C:15]1[CH:14]=[CH:13][C:7](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[C:6]([Cl:5])[C:16]=1[C... | COc1ccccc1Sc1ccc(C=CC(=O)O)c(Cl)c1Cl | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 2 | Boron tribromide (84 mL of a 1.0M solution in CH2Cl2) was added to a suspension of Example 310C in CH2Cl2 (85 mL) at 0° C. After addition was completed, the ice-water bath was removed, and the homogeneous dark solution was stirred for 2 hours before the mixture was poured into 1 N aqueous HCl (100 mL) and ice (100 g), ... | O=C(O)/C=C/c1ccc(Sc2ccccc2O)c(Cl)c1Cl | null | null | null |
1,703,106 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([NH:12]C(=O)C)[CH3:11])=[N:8][CH:9]=1>>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([NH2:12])[CH3:11])=[N:8][CH:9]=1 | CC(=O)NC(C)c1ccc(F)cn1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 27.5 | null | A mixture of 5N aqueous NaOH solution (5 mL) and N-(1-(5-fluoropyridin-2-yl)ethyl)acetamide (180 mg, 0.4 mmol) was heated under reflux conditions for 12-16 h. After completion of the reaction, the reaction mixture was cooled to a temperature of 20-35° C. The reaction mixture was extracted with DCM, dried over anhydrous... | CC(N)c1ccc(F)cn1 | null | 80.3 | null |
1,008,248 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [O:1]([C:8]1[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=1)[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]2[CH2:21][C@H:20]2[C:22](O)=[O:23])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:52][C:53]([F:57])([F:56])[CH2:54][NH2:55]>ClCCl.CN(C=O)C>[O:1]([... | NCC(F)(F)F | O=C(O)[C@@H]1C[C@H]1c1ccc(NCc2cccc(Oc3ccccc3)c2)cc1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | null | 0.25 | To a mixture of racemic-(trans)-2-{4-[(3-phenoxybenzyl)amino]phenyl}cyclopropanecarboxylic acid (I-2a) (0.15 g, 0.41 mmol) in dichloromethane (3 mL) and DMF (1 mL) was added HATU (0.23 g, 0.62 mmol). The mixture was stirred for 15 mins followed by addition of 2,2,2-trifluoroethylamine (0.08 g, 0.82 mmol). The solution ... | O=C(NCC(F)(F)F)[C@@H]1C[C@H]1c1ccc(NCc2cccc(Oc3ccccc3)c2)cc1 | null | 55 | null |
914,097 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][C:19]([C:24]([N:26]3[CH2:31][CH2:30][C:29]([F:33])([F:32])[CH2:28][CH2:27]3)=[O:25])=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:34][C:35]([F:46])([F:45])[C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[C... | OB(O)c1cccc(C(F)(F)F)c1 | O=C(c1ccc2[nH]c(C(=O)N3CCC(F)(F)CC3)cc2c1)N1CCC(N2CCCCC2)CC1 | null | [Cu+2] | CC(=O)[O-] | 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 | null | null | The title compound was synthesized in analogy to example 66, from [5-([1,4′]bipiperidinyl-1′-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone (example 168), 3-(trifluoromethyl)phenylboronic acid, copper(II) acetate and pyridine in dichloromethane, to give the desired product as a brown oil (66%). | O=C(c1ccc2c(c1)cc(C(=O)N1CCC(F)(F)CC1)n2-c1cccc(C(F)(F)F)c1)N1CCC(N2CCCCC2)CC1 | null | 66 | null |
1,197,208 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | C(O[C:4](=[O:14])[C:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[CH:6]O)C.[NH:15]([C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=1)[NH2:16]>>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2[C:4](=[O:14])[N:15]([C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:20]=[CH:19][N:18]=3)[NH:16][CH:... | CCOC(=O)C(=CO)c1cccnc1 | NNc1cc(C(F)(F)F)ccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The compound is prepared analogously to Example 2 from 18 mg (0.09 mmol) of the compound from Example 2A and 18 mg (0.10 mmol) 2-hydrazino-4-(trifluoromethyl)pyridine [R. A. Evans, C. Wentrup, J. Chem. Soc. Chem. Commun. 15, 1062-1064 (1992)]. 11.7 mg (41% of th.) of the title compound are obtained as a yellow solid. | O=c1c(-c2cccnc2)c[nH]n1-c1cc(C(F)(F)F)ccn1 | null | null | null |
1,529,412 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]([O:4][CH2:5][C:6]1[C:7]([N:40]2[CH2:51][CH2:50][N:49]3[C:42](=[CH:43][C:44]4[CH2:45][C:46]([CH3:53])([CH3:52])[CH2:47][C:48]=43)[C:41]2=[O:54])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:13]=[C:14]([NH:20][C:21]2[N:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[C:15... | CC(=O)OCc1c(-c2cc(Nc3ccc(N4CCN(C(=O)OC(C)(C)C)CC4)cn3)c(=O)n(C)c2)ccnc1N1CCn2c(cc3c2CC(C)(C)C3)C1=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 4 | A mixture of 339d (130 mg, 0.18 mmol) and HCl/methanol (4.0 mL) was stirred at room temperature for 4 h. It was then concentrated under reduced pressure to afford crude 339e (100 mg, 87%), which was used in the next step without further purification. MS-ESI: [M+H]+ 637.3. | CC(=O)OCc1c(-c2cc(Nc3ccc(N4CCNCC4)cn3)c(=O)n(C)c2)ccnc1N1CCn2c(cc3c2CC(C)(C)C3)C1=O | null | 87.2 | null |
567,400 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | [O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][C:23]=1[CH:24]=O.C(O)=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2... | COc1ccc(C=O)c(OC)c1OC | c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 120 | null | A mixture of 1.27 g of the compound (9) synthesized in Example 2 and 0.8 g of 2,3,4-trimethoxybenzaldehyde was stirred at 120° C., then, 0.18 ml of formic acid was added dropwise. This was stirred for one hour at the same temperature, then ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate were ... | COc1ccc(CN2CCC(c3ccc(Oc4ccccc4)cc3)CC2)c(OC)c1OC | null | 73 | null |
495,553 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [NH2:1][C@@H:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])(OCC)=O>>[C:30]1(=[O:39])[N:1]([C@@H:2]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10... | COC(=O)C[C@@H](N)c1ccc(OC)c(OC)c1 | CCOC(=O)N1C(=O)c2ccccc2C1=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 | null | null | Methyl (3R)-3-amino-3-(3,4-dimethoxyphenyl)propionate (0.25 g, 0.91 mmol), sodium carbonate (0.10 g, 0.91 mmol) and N-carboethoxyphthalimide (0.20 g, 0.91 mmol) were allowed to react according to the procedure of Example 85. Methyl (3R)-3-phthalimido-3-(3,4-dimethoxyphenyl)propionate was obtained as a white powder, 0.2... | COC(=O)C[C@H](c1ccc(OC)c(OC)c1)N1C(=O)c2ccccc2C1=O | null | null | null |
1,152,786 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH:24]1([N:30]=[C:31]=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]([N:17]([C:18]3[CH:19... | O=C=NC1CCCCC1 | Clc1ccc(-n2nc3ccccc3c2Nc2ccccc2)cc1 | 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 | In analogy to the procedure described in example 1.2, [2-(4-chloro-phenyl)-2H-indazol-3-yl]-phenyl-amine was reacted with cyclohexylisocyanate ([3173-53-3]) in toluene for 5 days under reflux conditions to give the title compound as yellow oil. MS: m/e=445.1 [M+H+]. | O=C(NC1CCCCC1)N(c1ccccc1)c1c2ccccc2nn1-c1ccc(Cl)cc1 | null | null | null |
1,492,201 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[N:12][OH:13])=[CH:10][C:5]=2[C:4]([CH3:15])([CH3:14])[O:3]1.C1C(=O)N([Cl:23])C(=O)C1>CN(C=O)C>[OH:13]/[N:12]=[C:11](\[Cl:23])/[C:9]1[CH:8]=[CH:7][C:6]2[B:2]([OH:1])[O:3][C:4]([CH3:15])([CH3:14])[C:5]=2[CH:10]=1 | O=C1CCC(=O)N1Cl | CC1(C)OB(O)c2ccc(C=NO)cc21 | 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 | 45 | 3 | To a solution of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oxime (1.38 g, 6.73 mmol) in DMF (15 mL) at rt was added NCS (1.07 g, 8.03 mmol). The reaction mixture was warmed to 45° C., stirred for 3 h and cooled to rt. The mixture was poured into ice-water (20 mL) and extracted with EA (20 ... | CC1(C)OB(O)c2ccc(/C(Cl)=N/O)cc21 | null | 105.5 | null |
925,254 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [CH2:1]([O:3][C:4](=[O:19])[C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=1[N+:15]([O-])=O)[CH3:2].[H][H]>CCO>[CH2:1]([O:3][C:4]([C:5]1[NH:15][C:8]2[C:7]([CH:6]=1)=[CH:12][CH:11]=[C:10]([C:13]#[N:14])[CH:9]=2)=[O:19])[CH3:2] | [H][H] | CCOC(=O)C(=O)Cc1ccc(C#N)cc1[N+](=O)[O-] | 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 | Add to 1.5 g of 3-(4-cyano-2-nitrophenyl)-2-oxopropionic acid ethyl ester, in EtOH (40 mL) 10% Pd/C (0.45 g) and stir under a hydrogen atmosphere until the theoretical amount of hydrogen is absorbed. Filter the mixture and concentrate the filtrate to afford 1.1 g of crude product. Purify by chromatography on SiO2 and e... | CCOC(=O)c1cc2ccc(C#N)cc2[nH]1 | null | 65.3 | null |
666,328 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31]>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:18][CH2:19][CH2:20][N:21]2[C:25](=[O:26])[C:24]3=[CH:2... | NCCc1ccc(Cl)cc1 | O=C1c2ccccc2C(=O)N1CCCBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | 16 | To a mixture of 2-(4-chlorophenyl)ethylamine (1.56 g, 10 mmol) and potassium carbonate (2.8 g, 20 mmol) in CH3CN (50 ml) was added N-(3-bromopropyl)phthalimide (3.0 g, 11 mmol). The mixture was refluxed under stirring for 16 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the residue wa... | O=C1c2ccccc2C(=O)N1CCCNCCc1ccc(Cl)cc1 | null | 66.5 | null |
20,296 | ord_dataset-2a1960001e7d4e89987253631df1362a | null | 1977-01-01T00:02:00 | true | C(O[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]=1)C.[NH:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][N:17]=1)[NH2:15]>CO>[N:15](=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][NH:5]1)[N:14]=[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[... | NNC1=NCCc2ccccc21 | CCOC1=NCCc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-ethoxy-3,4-dihydroisoquinoline (4.25 g.) and 1-hydrazino-3,4-dihydroisoquinoline (3.9 g.) in methanol (40 ml.) was stirred at room temperature overnight and then at reflux for a day. More 1-ethoxy-3,4-dihydroisoquinoline (1 g.) was added during the reflux period. The solution was stripped of methanol an... | c1ccc2c(c1)CCNC2=NN=C1NCCc2ccccc21 | null | null | null |
1,257,891 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [NH2:1][C:2]([CH:4]1[CH2:9][O:8][CH2:7][CH2:6][N:5]1C(OC(C)(C)C)=O)=[O:3].O1CCOCC1.[ClH:23]>>[ClH:23].[NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH:4]1[C:2]([NH2:1])=[O:3] | CC(C)(C)OC(=O)N1CCOCC1C(N)=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | null | 1,1-Dimethylethyl 3-(aminocarbonyl)morpholine-4-carboxylate (0.48 g, 2.085 mmol) was taken up in 4 M HCl in dioxane (5 mL, 10.00 mmol) and maintained at room temperature overnight. The solvent was removed in vacuo to afford the title compound as a pale yellow solid. | NC(=O)C1COCCN1 | null | null | null |
127,726 | ord_dataset-e61c1950b2fc468dbf0701c65768f73f | null | 1985-01-01T00:03:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]12([NH:18][S:19]([C:22]3[CH:33]=[C:26]4[C:27](OC(=O)[NH:31][C:25]4=[CH:24][CH:23]=3)=[O:28])(=[O:21])=[O:20])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:27](=[O:28])[C:26]2[C:25](=[C... | O=c1[nH]c2ccc(S(=O)(=O)NC34CC5CC(CC(C5)C3)C4)cc2c(=O)o1 | CN1CCNCC1 | 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 | 25 | null | 2.7 g of 1-methylpiperazine are added slowly to a suspension of 10.2 g of 5-[N-(1-adamantyl)-sulfamoyl]-isatoic anhydride in 250 ml of absolute toluene, at 100° with stirring. After the addition is ended, the mixture is stirred for a further 1 hour at 100° and is allowed to cool to room temperature, the precipitate is ... | CN1CCN(C(=O)c2cc(S(=O)(=O)NC34CC5CC(CC(C5)C3)C4)ccc2N)CC1 | null | null | null |
372,905 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | C[O-].[Na+].I.[CH2:5]([S:7][C:8](=[NH:10])[NH2:9])[CH3:6].C(O[CH:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17])C>CCO>[NH2:19][C:18]1[C:15]([C:16]#[N:17])=[CH:14][N:9]=[C:8]([S:7][CH2:5][CH3:6])[N:10]=1 | CCOC=C(C#N)C#N | CCSC(=N)N | null | C[O-] | I | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | A suspension of NaOMe (2.7 g, 50 mmol) in EtOH (200 mL) is added to a mixture of S-ethylisothiourea hydroiodide (11.58 g, 50 mmol), ethoxymethylidenemalononitrile (6.1 g, 50 mmol) and ethanol (250 mL) at 25° C. The reaction mixture is refluxed under N2 for 2 h, and then the solution is concentrated on a hot plate until... | CCSc1ncc(C#N)c(N)n1 | null | 44.6 | null |
1,666,389 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19]1[CH:20]=[C:21]([C:24](Cl)=[O:25])[NH:22][N:23]=1>N1C=CC=CC=1>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][C:24]([C:21]2[NH:22][N:23]=[C:19]([C:13]3[CH:14]=[CH:15][C:16]([Cl:18... | O=C(Cl)c1cc(-c2ccc(Cl)cc2Cl)n[nH]1 | NCCc1ccc(O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | In pyridine (6 ml), 4-(2-amino-ethyl)-phenol (72 mg) was dissolved, and 5-(2,4-dichlorophenyl)-2H-pyrazole-3-carboxylic acid chloride (137 mg) was added thereto under an ice cooling while stirring. Thereafter, the mixture was stirred at a room temperature for 17 hours and then concentrated under a reduced pressure, and... | O=C(NCCc1ccc(O)cc1)c1cc(-c2ccc(Cl)cc2Cl)n[nH]1 | null | 70.6 | null |
809,008 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[NH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:22]=1[F:23]>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[N:13]([C:20]3[CH:19]=[CH:18][C:17]([F:16])=[C:22]([F:23])[CH:21]=3)[CH:14]=2)[CH:5]=... | OB(O)c1ccc(F)c(F)c1 | Cc1nc(C#Cc2ccnc(Cl)c2)c[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, MS: m/e=330.4 (M+H+), was prepared in accordance with the general method of example 7 from 2-chloro-4-(2-methyl-1 H-imidazol-4-ylethynyl)-pyridine and 3,4-difluorobenzene boronic acid. | Cc1nc(C#Cc2ccnc(Cl)c2)cn1-c1ccc(F)c(F)c1 | null | null | null |
429,888 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][C:9]3=[N:12][CH:13]=[CH:14][N:8]3[CH2:7][C:6]=2[CH:15]=1.[CH3:16][C:17]1[CH:34]=[CH:33][CH:32]=[CH:31][C:18]=1[C:19]([NH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)=[O:20].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:26]([C:25]3[CH:24... | Clc1ccc2c(c1)Cn1ccnc1CN2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 3 | As described for Example 125 a mixture of 1 mmol of 7-chloro-10,11-dihydro-5H-imidazo[2,1-c][1,4]benzodiazepine, 1.1 mmol of 4-[(2-methylbenzoyl)amino]benzoyl chloride and 1.5 mmol of triethylamine in 10 ml of dichloromethane is stirred at room temperature for 3 hours and worked up to give the desired product as a soli... | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3nccn3Cc3cc(Cl)ccc32)cc1 | null | null | null |
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