original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,449,262 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].[OH:17][C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[O:24][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[... | Oc1cccc(O)c1 | CO/C=C(/C(=O)OC)c1ccccc1CBr | 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 | null | To a solution of (E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate (0.5 g, 1.7 mmol) and 3-hydroxyphenol (0.2 g, 2.1 mmol) in 20 mL of acetonitrile (CH3CN) was added potassium carbonate (0.35 g, 2.6 mmol). The reaction mixture was stirred under reflux and concentrated in a vacuum to remove the solvent. The residue... | CO/C=C(/C(=O)OC)c1ccccc1COc1cccc(O)c1 | null | 74.9 | null |
1,346,567 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[NH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=1.CC(O)C.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[CH3:17][O:16][C:13]1[N:14]=[CH:15][C:10]([NH:9][C:2]2[CH:3]=[C:4]([NH2:8])[N:5]=[CH:6][N:7]=2)=[CH:11][CH:12]=1 | Nc1cc(Cl)ncn1 | COc1ccc(N)cn1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 90 | 36 | A mixture of 6-chloro-pyrimidin-4-ylamine (0.65 g, 5 mmol), 5-amino-2-methoxypyridine (0.62 g, 5 mmol) and 2-propanol (5 mL) is shaken for 36 h at 90° C. After cooling to room temperature, the reaction mixture is distributed between half-saturated Na2CO3-solution and ethyl acetate. The organic layer is dried over Na2SO... | COc1ccc(Nc2cc(N)ncn2)cn1 | null | null | null |
1,767,760 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | FC1C(C(O)=O)=C([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)C(C)=CC=1.[F:17][C:18]1[C:19]([CH3:28])=[C:20]([C:24](I)=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22]>>[F:17][C:18]1[C:19]([CH3:28])=[C:20]([C:24]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22] | Cc1c(F)ccc(I)c1C(=O)O | Cc1ccc(F)c(C(=O)O)c1-n1nccn1 | null | null | null | null | null | null | null | 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 following the same general protocol as described for 6-fluoro-3-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid in Example A352 using 3-fluoro-6-iodo-2-methylbenzoic acid. MS (ESI) 222 (M+H). | Cc1c(F)ccc(-n2nccn2)c1C(=O)O | null | null | null |
333,690 | ord_dataset-ba1248d90e3e465693710bbc45866f37 | null | 1996-01-01T00:07:00 | true | [CH2:1]([O:3][C:4](=[O:27])[CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16]([NH:17][C:18](=O)[CH2:19][CH2:20]1)=[CH:15][CH2:14]3)[CH3:2]>C(O)(=O)C.[Pt]=O>[CH3:9][C@:8]12[CH2:25][CH2:24][C@H:23]3[C@@H:13]([CH2:14][CH2:15][C@@H:16]4[C@:21]3([CH3:22])[... | CCOC(=O)CO[C@H]1CC[C@H]2[C@@H]3CC=C4NC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | null | null | O=[Pt] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | The product of Step D, above, and platinum oxide (35 mg) in glacial acetic acid (2 ml) was hydrogenated at 40 psi for 22.5 hours. The mixture was filtered through a pad,of celite. The filtrate was concentrated and the residue purified via preparative TLC using one silica gel plate (1000μ) developed with EtOAc to give t... | CCOC(=O)CO[C@H]1CC[C@H]2[C@@H]3CC[C@H]4N=CCC[C@]4(C)[C@H]3CC[C@]12C | null | null | null |
295,723 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | [CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:26])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[C:14]([O:24][CH3:25])[CH:13]=2)[CH2:4][CH2:3]1.[H][H]>CO.[C].[Pd]>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9](=[O:26])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15](... | COc1cc(C=CC(=O)N[C@H]2CC[C@@H](C)CC2)ccc1OCCN(C)C | [H][H] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 0.05 g of 10% palladium-carbon was added to a solution of 1 g of N-(cis-4-methylcyclohexyl)-4-(2-dimethylaminoethoxy)-3-methoxycinnamamide (Example 107) in 50 ml of methanol. The solution was vigorously stirred for 16 hours under normal-pressure hydrogen gas. After reaction, the catalyst was filtered out, and the solve... | COc1cc(CCC(=O)N[C@H]2CC[C@@H](C)CC2)ccc1OCCN(C)C | null | null | null |
1,623,557 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | C(OC([NH:8][CH2:9][C@H:10]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH3:22])[CH2:17][CH2:16]1)[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C.[ClH:23].Cl.Cl.NC[C@H](N1CCN(CC2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)CC1)C(O)=O>>[ClH:23].[ClH:23].[ClH:23].[NH2:8][CH2:9][C@H:10]([N:15]1[CH2:16][CH2:17][N:18]([CH2:21][C:22]2[... | CCN1CCN([C@@H](CNC(=O)OC(C)(C)C)C(=O)OC)CC1 | NC[C@@H](C(=O)O)N1CCN(Cc2ccc(F)cc2)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In a manner similar to example 2-3, starting from 5.3 g (13.4 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-(4-ethylpiperazin-1-yl)propanoate, 5.4 g (100%) of (S)-3-amino-2-[4-(4-fluorobenzyl)piperazin-1-yl]propanoate trihydrochloride are obtained in the form of a beige solid. | COC(=O)[C@H](CN)N1CCN(Cc2ccc(F)cc2)CC1 | null | null | null |
1,654,026 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:12][CH2:13][C:14](OC)=O)[CH:6]=[N:7][C:8]=1[O:9][CH3:10].CC(C)([O-])C.[K+].BrC[C:26]1C=C[CH:29]=[C:28]([Cl:32])[CH:27]=1>C1COCC1>[Cl:32][C:28]1[CH:29]=[C:13]([CH:14]=[CH:26][CH:27]=1)[CH2:12][S:11][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[N:7][CH:6]=1 | COC(=O)CCSc1cnc(OC)c(OC)c1 | Clc1cccc(CBr)c1 | null | CC(C)(C)[O-] | [K+] | 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 | -45 | 0.33 | To a cooled solution of methyl 3-[(5,6-dimethoxypyridin-3-yl)sulfanyl]propanoate (Intermediate 7, 257 mg, 1 mmol) in THF (6 ml) at −45° C. was added potassium tert-butoxide (123 mg, 1.10 mmol). After stirring at −45° C. for 20 minutes, 1-(bromomethyl)-3-chlorobenzene (0.16 ml, 1.20 mmol) was added and the reaction mixt... | COc1cc(SCc2cccc(Cl)c2)cnc1OC | null | 82.5 | null |
1,141,807 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[C:15]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:14]=3[O:13][CH2:12]2)=[O:10])=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].[Cl:25][C:26]1[N:31]=[C:30](Cl)[CH:29]=[CH:28][N:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN1C(=O)CCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]... | Clc1ccnc(Cl)n1 | O=C(Nc1ccc(Cl)c(C(F)(F)F)c1)N1COc2cc(O)ccc21 | null | O=P([O-])([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | null | To a solution of 290 mg (0.81 mMol) 6-hydroxy-benzooxazole-3-carboxylic acid (4-chloro-3-trifluoromethyl-phenyl)-amide (Step 1.3) and 134 mg (0.90 mMol) 2,4-dichloropyrimidine in 15 ml NMP, 377 mg (1.78 mMol) K3PO4 are added. After 2 h at rt the reaction mixture is dissolved in EtOAc and water, the aq. phase separated ... | O=C(Nc1ccc(Cl)c(C(F)(F)F)c1)N1COc2cc(Oc3ccnc(Cl)n3)ccc21 | null | null | null |
1,272,266 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18](B(O)O)[CH:17]=[CH:16]2.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C... | COc1ccc2cc(B(O)O)ccc2c1 | O=[N+]([O-])c1ccccc1I | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 110 | 7 | To a suspension of 2-iodo-1-nitrobenzene (2.5 g), (6-methoxynaphthalen-2-yl)boronic acid (2.9 g) and tetrakis(triphenylphosphine)palladium(0) (600 mg) in toluene (50 ml) was added an aqueous solution of 2N sodium carbonate (15 ml) under a nitrogen atmosphere, and the solution was stirred for 7 hours at 110° C. Ethyl ac... | COc1ccc2cc(-c3ccccc3[N+](=O)[O-])ccc2c1 | null | 42.8 | null |
755,740 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | Br[C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)... | Cc1oc(-c2cccc(Br)c2)nc1CCO | OB(O)c1ccc(F)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCO | null | null | null | null | null | null | null | null | null | null | 85 | 0.5 | 2-[2-(3-Bromo-phenyl)-5-methyloxazol-4-yl]ethanol (1.0 g, 3.54 mmol) (see Ex. 2, Part D) and para-fluorophenyl boronic acid (744 mg, 5.32 mmol) were stirred in n-PrOH (10 mL) under nitrogen, to which 2M Na2CO3 (3.54 mL) was added. The mixture was heated at 85° C., and after Pd(PPh3)4 (41 mg, 0.0354 mmol) was added, the... | Cc1oc(-c2cccc(-c3ccc(F)cc3)c2)nc1CCO | null | 35.6 | null |
1,157,427 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:6]=CNN=1.CO[C:9]([C:11]1[S:12][C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:14][CH:15]=1)=[O:10]>>[C:16]([C:13]1[S:12][C:11]([C:9](=[O:10])[CH2:6][C:2]#[N:1])=[CH:15][CH:14]=1)([CH3:19])([CH3:18])[CH3:17] | Nc1cc[nH]n1 | COC(=O)c1ccc(C(C)(C)C)s1 | null | null | null | null | null | null | null | 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 was prepared according to the general procedure for aminopyrazole synthesis (route A1) from 5-tert-Butyl-thiophene-2-carboxylic acid methyl ester (3.0 g, 15.0 mmol, 1.0 eq). The crude product was extracted with DCM and used in the following step without further purification (2.7 g, yield: 86%). | CC(C)(C)c1ccc(C(=O)CC#N)s1 | null | 86 | null |
1,370,747 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([NH:15][C:16](=[O:20])OCC)=[N:5]2.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([O:13][CH3... | COc1cc(OC)cc(N2CCNCC2)c1 | CCOC(=O)Nc1nc2cc(F)c(F)cc2nc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Ethyl N-(6,7-difluoro-2-methoxyquinoxalin-3-yl)carbamate and 1-(3,5-dimethoxyphenyl)piperazine were reacted by the same way with the example 169 to obtain the titled compound (yield, 70%). MS (ESI) m/z 460 ([M+H]+). | COc1cc(OC)cc(N2CCN(C(=O)Nc3nc4cc(F)c(F)cc4nc3OC)CC2)c1 | null | 70 | null |
53,483 | ord_dataset-3d470a6df4a04b1996e024a38c53e818 | null | 1979-01-01T00:03:00 | true | [CH2:1]([NH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:39][CH2:40][CH:41](CO)[OH:42]>>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O... | OCC(O)CO | CCCCCCCCCCCCCCCCNc1ccc(C(=O)OC)cc1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 180 | null | A mixture of 2.25 g of methyl 4-(n-hexadecylamino)benzoate, 280 mg of glycerol, and 1.37 g of p-toluenesulfonic acid is heated at 180° C. for 18 hours and then is partitioned between ether and 3% aqueous sodium carbonate solution. The ether layer is separated, dried, and evaporated to yield 2,3-dihydroxypropyl 4-(n-hex... | CCCCCCCCCCCCCCCCNc1ccc(C(=O)OCC(O)CO)cc1 | null | null | null |
875,701 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:21]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][C:19]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)=[N:18]3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:37][CH2:38][C:39]([O:41]CC)=[O:40].[OH-].[Na+].Cl... | CCOC(=O)CCc1ccc(OCc2ccc(Cn3nc(-c4ccc(F)cc4)cc3CCc3ccccc3)cc2)cc1F | null | null | Cl | [Na+] | [OH-] | 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 | 25 | 1 | The oil obtained in Example 142 was dissolved in methanol (5 mL) and tetrahydrofuran (5 mL), and 2 N aqueous sodium hydroxide solution (2 mL) was added. The mixture was stirred at room temperature for 1 hr. The reaction mixture was neutralized with 6 N hydrochloric acid, and the mixture was extracted with ethyl acetate... | O=C(O)CCc1ccc(OCc2ccc(Cn3nc(-c4ccc(F)cc4)cc3CCc3ccccc3)cc2)cc1F | null | 11 | null |
822,883 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [F:1][C:2]([F:26])([F:25])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12](O)=[O:13])=[C:7]2[N:6]=[C:5]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH:4]=1.[NH2:27][C:28]1[CH:29]=[C:30]([S:34]([N:37]([CH3:39])[CH3:38])(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1>>[CH3:38][N:37]([CH3:39])[S:34]([C:30... | CN(C)S(=O)(=O)c1cccc(N)c1 | O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | null | null | null | null | null | null | null | 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 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) and 3-amino-N,N-dimethyl-benzenesulfonamide [CAS 6274-18-6; commercially available] according to general procedure II. Yellow solid. MS (ISP) 558.3 [(M+H)+]; mp 210° C. | CN(C)S(=O)(=O)c1cccc(NC(=O)c2cnn3c(C(F)(F)F)cc(-c4ccc(C(F)(F)F)cc4)nc23)c1 | null | null | null |
1,316,029 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:14]=[C:5]2[N:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[C:9]([CH3:10])[N:4]2[N:3]=1.O[N:16]=[C:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=1.N>>[CH3:1][C:2]1[CH:14]=[C:5]2[N:6]=[CH:7][C:8]([C:11]3[O:13][N:24]=[C:17]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[N:16]=3)=[C:9]([CH3:10])[N:4]2[N:3]... | NC(=NO)c1cccnc1 | Cc1cc2ncc(C(=O)O)c(C)n2n1 | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according Method C using 2,7-dimethylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (Maybridge) and N′-hydroxynicotinimidamide (Tyger). 1H NMR (300 MHz, DMSO-d6) δ2.52 (s, 3 H), 3.27 (s, 3 H), 6.77 (s, 1 H), 7.67 (ddd, J=8.0, 4.9, 0.7 Hz, 1 H), 8.48 (dt, J=8.6, 1.9 Hz, 1 H), 8.84 (dd, J=4.7... | Cc1cc2ncc(-c3nc(-c4cccnc4)no3)c(C)n2n1 | null | null | null |
479,350 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Cl[C:8]1[N:9]=[C:10]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]3[O:26][CH2:27][O:28][C:22]=3[CH:21]=2)[C:11]2[C:16]([CH3:17])=[CH:15][S:14][C:12]=2[N:13]=1>>[CH3:1][C:2]1[N:3]([C:8]2[N:9]=[C:10]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]4[O:26][CH2:27][O:28][C:22]=4[CH:21]=3)[C... | Cc1csc2nc(Cl)nc(NCc3ccc4c(c3)OCO4)c12 | Cc1ncc[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 | Following the procedure of Example 97, the reaction of 2-methylimidazole with 2-chloro-5-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine gives 2-(2-methylimidazol-1-yl)-5-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine. | Cc1csc2nc(-n3ccnc3C)nc(NCc3ccc4c(c3)OCO4)c12 | null | null | null |
218,485 | ord_dataset-640d007e35e243a286c8b7dd2b77ac1b | null | 1990-01-01T00:11:00 | true | O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[C:14]1([N:20]2[CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:23](=[O:31])[NH:22][C:21]2=[O:32])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:32]=[C:21]1[N:20]([C:14]2[CH:19]=[CH... | COC(=O)CCCCCCCCO | O=C1NC(=O)N(c2ccccc2)C1c1ccccc1 | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 25 | 72 | Diethyl axodicarboxylate (1.39 g, 8 mmol) in THF (5 mL, was added dropwise to a stirred solution of methyl 9-hydroxynonanoate (1.50 g, 8 mmol), 3,4-diphenylimidazolidine-2,5-dione (2.02 g, 8 mmol) obtained according to the procedure of K. C. Joshi, et al., J. Het. Chem., 18, 1651-1653 (1981) and triphenylphosphine (2.1... | COC(=O)CCCCCCCCN1C(=O)C(c2ccccc2)N(c2ccccc2)C1=O | null | 82.2 | null |
559,079 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | C([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH2:13])[C:8]([F:11])=[N:9][CH:10]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[CH:12]([C:7]1[C:8]([F:11])=[N:9][CH:10]=[C:5]([OH:4])[CH:6]=1)=[CH2:13] | C=Cc1cc(OC(C)=O)cnc1F | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a stirred solution of the 5-acetoxy-2-fluoro-3-ethenylpyridine from b above (1.40 g, 7.70 mmol) in MeOH (50 mL) was added K2CO3 (0.53 g, 3.90 mmol). The reaction mixture was allowed to stir at room temperature 24 h. The solvent was evaporated and the residue was diluted with Et2O (100 mL) and water (100 mL). The pha... | C=Cc1cc(O)cnc1F | null | 76 | null |
331,516 | ord_dataset-1558660634294cc8ad7e01746e9083fd | null | 1996-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:14][C:15]([O:17][CH3:18])=[O:16]>>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[N:10]=[N:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1 | COC(=O)CCl | Cc1cccc(-c2nnn[nH]2)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 | Feed materials: 5-(3-methylphenyl)tetrazole and methyl chloroacetate. | COC(=O)Cn1nnnc1-c1cccc(C)c1 | null | null | null |
1,513,069 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [CH3:1][C@@:2]12[O:9][C@@H:6]([CH2:7][CH2:8]1)[C:5](=[O:10])[CH2:4][C:3]2=[O:11].C(Cl)(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:28][C:29]1[CH:34]=[C:33]([CH2:35][CH3:36])[C:32]([Pb+3])=[C:31]([CH2:38][CH3:39])[CH:30]=1.Cl>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[Br:28][C:29]1[CH:34]=[C:33]([CH2:35][CH3:36])[C:32]([CH:4... | C[C@]12CC[C@H](O1)C(=O)CC2=O | CCc1cc(Br)cc(CC)c1[Pb+3] | null | CC(=O)[O-] | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 80 | null | (1R*,5S*)-1-Methyl-8-oxabicyclo[3.2.1]octane-2,4-dione (1 g, 6.5 mmol) and 4-dimethylamino-pyridine (3.96 g, 32.5 mmol) are added to a mixture of chloroform (20 ml) and toluene (5 ml). The reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature. 4-Bromo-2,6-diethylphenyllead triacetate (4.25 g, ... | CCc1cc(Br)cc(CC)c1C1C(=O)[C@@H]2CC[C@@](C)(O2)C1=O | null | 4.2 | null |
1,381,294 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH:1]1([C:5]2[CH:9]=[C:8]([NH:10][C:11](=[O:19])OC3C=CC=CC=3)[N:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[N:34]=[CH:33][N:32]=[C:31]2[S:40][C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][CH:47]=1)[NH2:44]>>[CH:1]1([... | COc1cc2ncnc(Sc3cccc(N)c3)c2cc1OC | O=C(Nc1cc(C2CCC2)nn1-c1ccccc1)Oc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1-(3-cyclobutyl-1-phenyl-1H-pyrazol-5-yl)-3-(3-(6,7-dimethoxyquinazolin-4-ylthio)phenyl)urea was prepared from phenyl 3-cyclobutyl-1-phenyl-1H-pyrazol-5-ylcarbamate and 3-(6,7-dimethoxyquinazolin-4-ylthio)aniline (prepared as described in Example 115B) according to the procedure given in Example 352B. 1H NMR (400 MHz, ... | COc1cc2ncnc(Sc3cccc(NC(=O)Nc4cc(C5CCC5)nn4-c4ccccc4)c3)c2cc1OC | null | null | null |
52,688 | ord_dataset-3d470a6df4a04b1996e024a38c53e818 | null | 1979-01-01T00:03:00 | true | [CH3:1][CH2:2][C:3]1[C@H:8]2[N:9]3[CH2:11][CH2:12][C:13]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[NH:15][C:14]=4[C@@:7]2([C:22]([O:24][CH3:25])=[O:23])[CH2:6][C@@H:5]([CH2:10]3)[CH:4]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl>[CH3:1][CH2:2][C:3]1[C@H:8]2[N@+:9]3([O-:34])[CH2:11][CH2:12][C:13]4[C:21]5[C:16](=[CH:17][... | CCC1=C[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@](C(=O)OC)(C2)[C@@H]13 | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 0.25 | To a solution of catharanthine (201 mg, 0.60 mmol) in methylene chloride (40 ml) at -15° C. was added a solution of m-chloroperbenzoic acid (111 mg, 0.65 mmol) and the solution stirred for 15 min. To the catharanthine N-oxide thus formed was added a solution of vindoline (270 mg, 0.59 mmol) in methylene chloride. The a... | CCC1=C[C@H]2C[C@]3(C(=O)OC)c4[nH]c5ccccc5c4CC[N@+]([O-])(C2)[C@H]13 | null | null | null |
172,859 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | [CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:2].C(=O)(O)[O-].[Na+].[CH2:21](I)[CH3:22].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[C:11]([C:12]([O:14][CH2:21][CH3:22])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:2] | CCOC(=O)Cc1ncccc1C(=O)O | CCI | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 50 | 24 | To a mixture of 54 g (0.26 mole) of 3-carboxy-2-pyridineacetic acid ethyl ester* and 24.4 g (0.29 mole) of sodium bicarbonate in 300 ml of dimethylformamide was added 60.8 g (0.39 mole) of ethyliodide. The mixture was stirred at 50° C. for 24 hr; cooled to 25° C. and treated with 300 ml of water. The aqueous solution w... | CCOC(=O)Cc1ncccc1C(=O)OCC | null | null | null |
791,098 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | C([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.C[O-].[Na+].Cl>O1CCCC1.CO>[CH3:20][O:19][C:18]1[C:13]([NH:12][C:10]([NH2:9])=[S:11])=[CH:14][C:15]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[N:16][CH:17]=1 | COc1cnc(N2CCOCC2)cc1NC(=S)NC(=O)c1ccccc1 | null | null | C[O-] | Cl | [Na+] | 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 | 2 | To a stirred solution of 5.80 g (15.6 mmol) 1-benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea in 100 ml tetrahydrofuran and 25 ml methanol heated at 60° C. was added dropwise 1.15 ml (6.23 mmol) 5.4 M sodium methylate solution and stirring continued for 2 h at 60° C. 1.2 ml concentrated hydrochloric acid w... | COc1cnc(N2CCOCC2)cc1NC(N)=S | null | 83.9 | null |
1,614,805 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([O:24][CH3:25])[CH:16]=2)[N:10]=1>Cl.[Fe].CO>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([N:11]2[C:12](=[O:14])[NH:13][C:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:10]2)=[C... | COc1cc(-n2nc(-c3c(F)cccc3Cl)[nH]c2=O)ccc1[N+](=O)[O-] | null | null | [Fe] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the procedure described in step-2 of Intermediate-28 by using 3-(2-chloro-6-fluorophenyl)-1-(3-methoxy-4-nitrophenyl)-1H-1,2,4-triazol-5(4H)-one (0.100 g), iron powder (catalytic), conc.HCl (5-6 drops) and methanol (5 mL) to afford 0.070 g of desired product. 1H NMR (300 MHz... | COc1cc(-n2nc(-c3c(F)cccc3Cl)[nH]c2=O)ccc1N | null | 76.3 | null |
899,163 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[C:17]([O:25][C:26]2[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=2)[CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[ClH:66]>C1COCC1.O1CCOCC1>[ClH:66].[F:22][C:21]([F... | CC(C)(C)OC(=O)N1CCC(O)CC1 | Oc1ccc(Oc2ccc(C(F)(F)F)cc2)cc1 | null | CC(C)OC(=O)N=NC(=O)OC(C)C | Cl | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a solution of t-butyl-4-hydroxy-1-piperidine carboxylate (1.0 g, 5.0 mmol) in anhydrous THF (5 mL) was added 4-[(4-trifluoromethyl)phenoxy]phenol (1.65 g, 6.5 mmol) in THF (5 mL) and triphenyl phosphine (1.57 g, 6 mmol) in THF (5mL). The resulting mixture was cooled to 0° C. using ice-water bath and purged with nitr... | FC(F)(F)c1ccc(Oc2ccc(OC3CCNCC3)cc2)cc1 | null | 65 | null |
422,302 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [BH4-].[Na+].[CH2:3]([C:5]1([CH2:17][CH3:18])[CH2:10][O:9][C:8]2([CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[O:7][CH2:6]1)[CH3:4]>C(O)C>[CH2:17]([C:5]1([CH2:3][CH3:4])[CH2:6][O:7][C:8]2([CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[O:9][CH2:10]1)[CH3:18] | CCC1(CC)COC2(CCC(=O)CC2)OC1 | 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 | 1 | 820 mg (21.5 mmol) of sodium borohydride were added to a solution of 13 g (57.4 nmol) of 3,3-diethyl-1,5-dioxaspiro[5.5]undecan-9-one in 200 ml of ethanol and the mixture was stirred at room temperature for 1 hour. To complete the reaction, the mixture was heated at 40° C. for a further 15 hours. To destroy excess sodi... | CCC1(CC)COC2(CCC(O)CC2)OC1 | null | null | null |
1,760,429 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH2:1]([NH:7][C:8]([N:10]1[CH:15]=[C:14]([NH:16][CH3:17])[C:13](=[O:18])[NH:12][C:11]1=[O:19])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:20]([N:16]([CH3:17])[C:14]1[C:13](=[O:18])[NH:12][C:11](=[O:19])[N:10]([C:8]([NH:7][CH2:1][CH2:2][CH2... | O=C(Cl)c1ccccc1 | CCCCCCNC(=O)n1cc(NC)c(=O)[nH]c1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 18 | N-hexyl-5-methylamino-2,4-dioxo-pyrimidine-1-carboxamide (0.08 g, 0.30 mmol) was dissolved in dry pyridine (4 mL). To the resulting solution, benzoyl chloride (0.04 mL, 0.39 mmol) was added. The reaction was stirred at room temperature under nitrogen atmosphere for 18 hrs, then concentrated under reduced pressure. The ... | CCCCCCNC(=O)n1cc(N(C)C(=O)c2ccccc2)c(=O)[nH]c1=O | null | 44.8 | null |
766,290 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:2]1[O:4][CH2:3]1.[SH-:10].[Na+].[NH4+].[Cl-]>C(O)(C)C.O>[S:10]([CH2:3][CH:2]([OH:4])[CH2:1][O:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][CH:2]([OH:4])[CH2:1][O:5][CH2:6][CH2:7][CH2:8][CH3:9] | CCCCOCC1CO1 | [SH-] | null | [Cl-] | [NH4+] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | O | null | null | null | null | null | null | null | null | null | 90 | 3 | A solution of butyl glycidyl ether (2.91 g, 22.39 mmol) in isopropanol (5 mL) and H2O (1 mL) was added to sodium bisulfide (0.628 g, 11.20 mmol) under nitrogen in a 100 mL 3-neck round bottom flask equipped with a N2 inlet, a rubber septum, glass stopper and a magnetic stir bar. The mixture was heated at 90° C. and mon... | CCCCOCC(O)CSCC(O)COCCCC | null | null | null |
1,233,746 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | FC(F)(F)C(O)=O.[CH:8]1([CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:29]=[CH:28][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[C:19]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH:18]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:29]=[CH:28][C:20]([C:21]([OH:23])=[O:22])=[C:19]... | CC(C)(C)OC(=O)c1ccc(/C=C/CC2CCCCC2)cc1Nc1ccc(F)cc1 | 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 | Trifluoroacetic acid 15 mL solution of the obtained tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 70-100%... | O=C(O)c1ccc(/C=C/CC2CCCCC2)cc1Nc1ccc(F)cc1 | null | null | null |
503,719 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][O:16][CH2:17][CH3:18].[I-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:14][CH2:15][O:16][CH2:17][CH3:18])=[C:4]([CH3:10])[CH:3]=1 | Cc1cc(Br)cc(C)c1O | CCOCCBr | null | [H-] | [I-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of 4-bromo-2,6-dimethylphenol (20 g) in DMF (10 ml) was added dropwise to a suspension of 60% sodium hydride (4.4 g) in DMF (50 ml) under ice-cooling, and the mixture was stirred under nitrogen atmosphere at room temperature for 2 hours. To the mixture were added bromoethylethyl ether (12.3 ml) and sodium io... | CCOCCOc1c(C)cc(Br)cc1C | null | null | null |
959,231 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[N:17]1([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(OCC)C>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5... | CO/C=C1/C(=O)NC(=O)c2ccc(I)cc21 | Nc1ccc(CN2CCCCC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOCC | null | null | null | null | null | null | null | null | null | 120 | 8 | To a solution of 0.2 g (0.60 mmol) of (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione in 2 mL of N,N′-dimethylformamide is added 4-piperidin-1-ylmethyl-phenylamine (0.127 mL, 0.67 mmol). The reaction mixture is heated at 120° C. under N2 for 1.5 h. After cooling, ethyl ether is added and left in refrigera... | O=C1NC(=O)c2ccc(I)cc2/C1=C/Nc1ccc(CN2CCCCC2)cc1 | null | 48.9 | null |
1,444,975 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][C:2](=[O:20])[CH2:3][CH2:4][NH:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:17][CH2:16][C:15](=O)[CH2:14]2)=[CH:9][CH:8]=1.Cl.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C@H:29]([NH2:31])[CH3:30])=[CH:25][C:24]=1[O:32][CH3:33]>>[NH2:1][C:2](=[O:20])[CH2:3][CH2:4][NH:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:... | COc1cc([C@@H](C)N)ccc1F | NC(=O)CCNC(=O)c1ccc([C@H]2CCC(=O)C2)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | General procedure B was followed using N-(3-amino-3-oxo-propyl)-4-[(1S)-3-oxocyclopentyl]benzamide as the ketone and (1R)-1-(4-fluoro-3-methoxyphenyl)-ethylamine hydrochloride as the amine. 1H NMR (600 MHz, DMSO) δ 8.39 (t, J=5.6 Hz, 1H), 7.74 (d, J=8.3 Hz, 2H), 7.37-7.31 (m, 3H), 7.16 (dd, J=8.6, 1.8 Hz, 1H), 7.10 (dd... | COc1cc([C@@H](C)NC2CC[C@H](c3ccc(C(=O)NCCC(N)=O)cc3)C2)ccc1F | null | null | null |
1,683,811 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH:24]3[CH2:28][O:27]C(C)(C)[O:25]3)[CH:23]=2)=[N:4][N:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][NH2:38]>C1(C)C=CC=CC=1.C(Cl)Cl>[C:12]1([C:10]2[CH:9]=[CH:8][CH:7]=[... | CC1(C)OCC(c2cncc(-c3nnc(Cl)c4c(-c5ccccc5)cccc34)c2)O1 | NCc1ccccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 100 | null | To a solution of 4-chloro-1-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5-phenylphthalazine (1.00 g, 2.39 mmol) in toluene (5 mL) was added pyridin-2-ylmethanamine (5.00 mL, 48.5 mmol) the contents were heated at 100° C. for 12 h. The reaction mixture was diluted with DCM (200 mL) and washed with 1.5N HCl (2 ×20 m... | OCC(O)c1cncc(-c2nnc(NCc3ccccn3)c3c(-c4ccccc4)cccc23)c1 | null | 5.1 | null |
102,500 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | [CH2:1]([O:3][C:4](=[O:21])[C@H:5]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:19]#[N:20])[NH:12][CH:11]=1)[NH:6][CH:7]=O)[CH3:2]>P(Cl)(Cl)(Cl)=O>[CH2:1]([O:3][C:4]([CH:5]1[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[C:19]#[N:20])[NH:12][C:11]=2[CH2:7][NH:6]1)=[O:21])[CH3:2] | CCOC(=O)[C@H](Cc1c[nH]c2cccc(C#N)c12)NC=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | 7.8 g of 4-cyano-N-formyltryptophan ethyl ester is dissolved at 0° C. in 40 ml of phosphorus oxychloride and stirred for 18 hours at room temperature. The solution is then concentrated by evaporation in vacuo, the residue partitioned between water and chloroform and the aqueous phase then extracted. The organic phases ... | CCOC(=O)C1Cc2c([nH]c3cccc(C#N)c23)CN1 | null | 4.1 | null |
1,280,280 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=1)[C:13]([O:15][CH3:16])=[O:14]>CO.[Pt](=O)=O>[ClH:2].[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[CH2:11][CH:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:17][CH2:18][NH:19]1 | COC(=O)c1ccnc(-c2ccc(Cl)cc2Cl)c1 | null | null | O=[Pt]=O | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 1.5 | Methyl 2-(2,4-dichlorophenyl)isonicotinate hydrochloride (2.60 g, 8.15 mmol) was dissolved in MeOH (50 mL), added platinum(IV) oxide (0.019 g, 0.08 mmol) and hydrogenated in a Büchi hydrogenator at 5 bar for 90 min. The reaction mixture was filtered and evaporated to give crude methyl 2-(2,4-dichlorophenyl)piperidine-4... | COC(=O)C1CCNC(c2ccc(Cl)cc2Cl)C1 | null | 211.7 | null |
834,704 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | Cl.Cl.[CH3:3][CH:4]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)=[O:18]>>[CH3:3][CH:4]([N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:19]2[CH:27]=[CH:26][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)=[O:18])[CH2:1... | CCCCCCC(C)N1CCNCC1 | O=Cc1ccc(C(=O)O)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from the product of Example 9 and 4-formylbenzoic acid. | CCCCCCC(C)N1CCN(C(=O)c2ccc(C=O)cc2)CC1 | null | null | null |
55,256 | ord_dataset-159c363342e44b539e7a5975c873e30d | null | 1979-01-01T00:05:00 | true | [O:1]1[CH2:6][CH2:5][N:4]([C:7]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH2:23])[CH2:12][CH2:11]2)=[O:8])[CH2:3][CH2:2]1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]([CH2:9][N:10]2[CH2:11][CH2:12][N:13]([... | O=C(Cl)c1ccccc1 | Nc1ccccc1CN1CCN(CC(=O)N2CCOCC2)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 | 8 | To a solution of 0.1 part of N1 -(morpholinocarbonylmethyl)-N4 -(2-aminobenzyl)piperazine in 3 volume parts of pyridine is added 0.062 part of benzoyl chloride, and the mixture is kept standing at room temperature overnight. Then the pyridine is distilled off under reduced pressure, and resultant residue is chromatogra... | O=C(Nc1ccccc1CN1CCN(CC(=O)N2CCOCC2)CC1)c1ccccc1 | null | null | null |
184,061 | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | null | 1989-01-01T00:02:00 | true | Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[OH:20][CH:21]1[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24][CH2:23][CH:22]1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.N12CCN(CC1)CC2>CS(C)=O>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]... | O=C(O)c1cn(C2CC2)c2cc(Cl)c(F)cc2c1=O | CC1(C)OCC(O)C(N2CCNCC2)CO1 | null | C1CN2CCN1CC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | 2.8 g (10 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are heated at 140° in 30 ml of dimethyl sulphoxide with 2.5 g (11 mmol) of 1-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine and 2.25 g (20 mmol) of 1,4-diazabicyclo[2.2.2]octane for 4 hours, the reaction mixture is co... | CC1(C)OCC(O)C(N2CCN(c3cc4c(cc3F)c(=O)c(C(=O)O)cn4C3CC3)CC2)CO1 | null | 10.5 | null |
1,492,442 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:7]1[CH:6]=[C:5]([C:8](=[O:10])[CH3:9])[CH:4]=[C:3]([C:11]([F:12])([F:13])[F:14])[C:2]=1[OH:1] | CC(=O)c1ccc(O)c(C(F)(F)F)c1 | O=C1CCC(=O)N1Br | 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 | -10 | 8 | 1-(4-Hydroxy-3-trifluoromethylphenyl)ethanone (5 g) was initially charged in acetonitrile (150 ml) at RT while stirring, and cooled to −10° C. At this temperature, N-bromosuccinimide (4.5 g, dissolved in 100 ml of acetonitrile) was added dropwise. Then the cooling bath was removed and the mixture was stirred for a furt... | CC(=O)c1cc(Br)c(O)c(C(F)(F)F)c1 | null | 99.5 | null |
1,420,261 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | C(N(CC)CC)C.[C:8](Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[NH2:15][C:16]1[N:21]=[C:20]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([F:30])[CH:23]=2)[CH:19]=[C:18]([N:31]2[C@H:36]([CH3:37])[CH2:35][O:34][C@H:33]([CH2:38][NH2:39])[CH2:32]2)[N:17]=1>C1COCC1>[NH2:15][C:16]1[N:17]=[C:18]([N:31]2[C@H:36]([CH3:37... | CC(C)(C)C(=O)Cl | C[C@@H]1CO[C@H](CN)CN1c1cc(-c2ccc(C#N)c(F)c2)nc(N)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.75 | Triethylamine (0.05 mL, 0.36 mmol) and pivaloyl chloride (0.04 mL, 0.33 mmol) were added to a solution of 4-{2-amino-6-[(2R,5R)-2-(aminomethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (99 mg, 0.29 mmol) in THF (5 mL), and the mixture was stirred at room temperature under nitrogen for 45 minutes. The... | C[C@@H]1CO[C@H](CNC(=O)C(C)(C)C)CN1c1cc(-c2ccc(C#N)c(F)c2)nc(N)n1 | null | 124.5 | null |
943,789 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | C([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:5])C.[OH-].[K+]>CO.O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][C:10]2[S:9][CH:8]=[N:7][C:6]=2[C:4]([OH:5])=[O:3])[CH:13]=1 | CCOC(=O)c1ncsc1Nc1cccnc1 | null | null | [K+] | [OH-] | 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 | 65 | 0.75 | A solution of 5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester (2.90 g, 11.63 mmol) in methanol (24.00 ml) was treated at room temperature with a solution of KOH (1.95 g, 34.90 mmol) in water (18 ml) and stirred at 65° C. for 2 h 45 min. The methanol was evaporated and the residual slurry acidified to pH 5 ... | O=C(O)c1ncsc1Nc1cccnc1 | null | 92.1 | null |
1,594,970 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[C:3](=O)[NH:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:3]1[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([S:8][CH3:9])[N:4]=1 | CSc1ncc(Cl)c(=O)[nH]1 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | A suspension of 5-chloro-2-(methylthio)pyrimidin-4(3H)-one (24 g, 0.136 mol) in POCl3 (200 mL) was heated at reflux for 2 hrs. The reaction mixture was then cooled to room temperature and was concentrated to remove excessive of POCl3. The residue was then treated with H2O (150 mL) and was adjusted to pH=7˜8 with aq. K2... | CSc1ncc(Cl)c(Cl)n1 | null | 86 | null |
1,321,562 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | Br[C:2]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:3]=1[CH2:4][N:5]1[C@@H:9]([CH3:10])[C@@H:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:7][C:6]1=[O:17].[CH3:26][O:27][C:28](=[O:47])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=1>>[CH3:26][O:27][C:28]... | COC(=O)Cc1ccc(OC)c(B2OC(C)(C)C(C)(C)O2)c1 | C[C@H]1[C@@H](c2ccccc2)OC(=O)N1Cc1cc(C(F)(F)F)ccc1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the procedure described in Example 1, Step 4, using the following starting materials: (4S,5R)-3-(2-bromo-5-trifluoromethyl-benzyl)-4-methyl-5-phenyl-oxazolidin-2-one and [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester. | COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN2C(=O)O[C@H](c3ccccc3)[C@@H]2C)c1 | null | null | null |
910,093 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([N:22](CC)CC)C.ClC(OCC)=O.[NH4+].[OH-]>O1CCCC1>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH2:22])=[O:19])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])... | CCN(CC)CC | CC(C)(C)[Si](C)(C)Oc1ccc(CCC(=O)O)cc1 | null | CCOC(=O)Cl | [NH4+] | [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 | null | 0.5 | 3-(4-tert-butyldimethylsilyloxyphenyl)propionic acid (2.13 g, 7.71 mmol) prepared in 3) was dissolved in tetrahydrofuran (32 ml) in nitrogen atmosphere, and triethylamine (1.16 ml, 8.41 mmol) and ethyl chloroformate (0.726 ml, 8.41 ml) were dropwise added under cooling with ice, followed by stirring for 30 minutes. The... | CC(C)(C)[Si](C)(C)Oc1ccc(CCC(N)=O)cc1 | null | 74.3 | null |
1,015,841 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | C([O:3][C:4]([O:6][N:7]=[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:9])=O)C.[OH-].[Na+].Cl>O.C(O)C>[C:10]1([C:8]2[NH:9][C:4](=[O:3])[O:6][N:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1 | CCOC(=O)ON=C(N)c1ccccc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | A solution of N′-[(ethoxycarbonyl)oxy]benzenecarboximidamide (17.0 g, 81.6 mmol) and sodium hydroxide (6.28 g, 157 mmol) in water (380 ml) and ethanol (95 ml) was stirred at room temperature for 3 hours. Thereto 1 N hydrochloric acid (157 ml) was added, and a precipitated solid was collected by filtration and washed wi... | O=c1[nH]c(-c2ccccc2)no1 | null | 53.3 | null |
972,189 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([C:14]2[CH2:18][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[N:15]=2)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.C[CH2:40][N:41](C(C)C)C(C)C>ClCCl.CN.ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=... | O=C(NS(=O)(=O)c1ccc(Cl)cc1)C1=NN(c2ccc(Cl)cc2)C(c2ccccc2)C1 | CCN(C(C)C)C(C)C | null | CN | Cl | ClP(Cl)(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | Clc1ccccc1 | null | null | null | null | null | null | null | null | null | 140 | null | Part B: A stirred mixture of N-[(4-chlorophenyl)sulfonyl]-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide (2.36 gram, 5 mmol), PCl5 (1.15 g, 5.5 mmol) and chlorobenzene (50 ml) is heated for 90 minutes at 140° C. After cooling the mixture to room temperature the residue is dissolved in dichlorometha... | CN=C(NS(=O)(=O)c1ccc(Cl)cc1)C1=NN(c2ccc(Cl)cc2)C(c2ccccc2)C1 | null | 14.8 | null |
1,074,414 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [CH3:1][N:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]34[CH2:29][CH:17]5[CH2:18][C:19]([NH:21]C(=O)OC(C)(C)C)([CH2:20]3)[CH:15]([CH2:16]5)[CH2:14]4)=[CH:9][CH:8]=2)[C:3]1=[O:30].C(Cl)Cl>[Pd].CO>[NH2:21][C:19]12[CH2:18][CH:17]3[CH2:29][C:13]([C:10]4[CH:9]=[CH:8][C:7]([N:4]5[CH2:5][CH2:6][N:2]([CH3:1])[C:3]5... | CN1CCN(c2ccc(C34CC5CC(C3)C(NC(=O)OC(C)(C)C)(C5)C4)cc2)C1=O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | To a stirred solution of the compound obtained from step I (0.25 g, 0.56 mmol) in a 1:1-mixture of CH2Cl2 and MeOH (10 mL) was added Pd/C (10% w/w, 0.1 g) and stirred at room temperature under H2 atmosphere for 2 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduce... | CN1CCN(c2ccc(C34CC5CC(C3)C(N)(C5)C4)cc2)C1=O | null | 86 | null |
1,741,605 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Br:1][C:2]1[CH:13]=[C:12]([O:14]C)[C:5]2[N:6]([CH:9]3[CH2:11][CH2:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1.B(Br)(Br)Br.N.CO>ClCCl>[Br:1][C:2]1[CH:13]=[C:12]([OH:14])[C:5]2[N:6]([CH:9]3[CH2:11][CH2:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1 | COc1cc(Br)cc2ncn(C3CC3)c12 | null | null | BrB(Br)Br | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | 35 | 5 | 5-bromo-1-cyclopropyl-7-methoxy-1H-benzo[d]imidazole (0.54 g, 2.01 mmol) was dissolved in dichloromethane (12 mL) under N2. A 1M BBr3 solution in DCM (12 mL, 12 mmol) was added dropwise over 1 min. The resulting stirred suspension was heated to 35° C. After 5 h, the reaction mixture was cooled in an ice water bath. A 7... | Oc1cc(Br)cc2ncn(C3CC3)c12 | null | null | null |
1,118,275 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | C(NC(C)C)(C)C.C([Li])CCC.[Li+].CC([N-]C(C)C)C.[F:21][C:22]1[CH:23]=[C:24]([N:28]2[C:32]([N:33]([CH3:37])[C:34](=[O:36])[CH3:35])=[C:31]([C:38]([O:40]CC)=O)[CH:30]=[N:29]2)[CH:25]=[CH:26][CH:27]=1>C1COCC1>[F:21][C:22]1[CH:23]=[C:24]([N:28]2[C:32]3[N:33]([CH3:37])[C:34](=[O:36])[CH:35]=[C:38]([OH:40])[C:31]=3[CH:30]=[N:2... | CCOC(=O)c1cnn(-c2cccc(F)c2)c1N(C)C(C)=O | null | null | CC(C)[N-]C(C)C | [Li+] | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)NC(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A solution of diisopropylamine (3.45 mL, 24.4 mmol) in 15 mL THF under argon at 0° C. was treated with n-butyllithium (14.7 mL of 1.6 M solution in hexanes, 23.5 mmol) and stirred at this temperature for 30 min. The freshly prepared LDA was added dropwise to a solution of ethyl 1-(3-fluorophenyl)-5-(N-methylacetamido)-... | Cn1c(=O)cc(O)c2cnn(-c3cccc(F)c3)c21 | null | null | null |
520,855 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+].[OH-].[Na+]>C(O)C>[CH2:16]([N:13]1[CH2:12][CH:11]=[C:10]([CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:15][CH2:14]1)[C... | c1ccc(CCCc2ccncc2)cc1 | BrCc1ccccc1 | null | [BH4-] | [Na+] | [OH-] | 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 | 0 | null | A solution of 1.7 g (8.6 mmol) of 4-(3-phenylpropyl)pyridine and 1.5 mL of benzylbromide in 5 mL of ethanol was stirred at rt for 0.5 h. To the reaction mixture was added 10 mL of ethanol and the mixture was cooled to 0° C. To this mixture was added 0.5 g (13.2 mmol) of NaBH4 small portions over a period of 1 h. To the... | C1=C(CCCc2ccccc2)CCN(Cc2ccccc2)C1 | null | null | null |
1,262,323 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | C([O:3][C:4](=[O:31])[CH2:5][C:6]1[O:10][N:9]=[C:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][C:13]=2[CH2:25][S:26][C:27]([CH3:30])([CH3:29])[CH3:28])[N:7]=1)C.[Li+].[OH-]>CO.O>[C:27]([S:26][CH2:25][C:13]1[CH:14]=[C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])(... | CCOC(=O)Cc1nc(Cc2ccc(NC(=O)C(C)(C)C)cc2CSC(C)(C)C)no1 | null | null | [Li+] | [OH-] | 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 | 6 | {3-[2-tert-Butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-benzyl]-[1,2,4]oxadiazol-5-yl}-acetic acid ethyl ester (0.28 mmol) in MeOH (5 mL) was treated with 1N aqueous LiOH (0.5 mL), and the reaction was stirred for 6 hours at room temperature. The mixture was diluted with H2O and extracted with EtOAc. The combine... | CC(C)(C)SCc1cc(NC(=O)C(C)(C)C)ccc1Cc1noc(CC(=O)O)n1 | null | null | null |
1,345,784 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7] | O=C1CCC(=O)N1Cl | CCOc1ccccc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 70 | To a solution of 2-ethoxybenzoic acid (4.4 g, 26.6 mmol) in 80 mL of acetonitrile at 0° C. was added N-chlorosuccinimide (3.7 g, 28 mmol) in 20 mL of acetonitrile dropwise over 30 minutes. The reaction mixture was warmed to ambient temperature and the mixture was allowed to stir for 70 hours. The mixture was quenched w... | CCOc1ccc(Cl)cc1C(=O)O | null | null | null |
1,072,289 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [CH2:1]([O:3][P:4]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:39][C:40]1[CH:45]=[C:44]([C:46]2[S:47][CH:48]=[CH:49][CH:50]=2)[CH:43]=[CH:42][C:41]=1[NH:51]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>CN(C=O)C>[NH2:51][C:41]1[CH:42]=[C... | CCOP(=O)(OCC)c1ccc(C(=O)O)cc1 | CC(C)(C)OC(=O)Nc1ccc(-c2cccs2)cc1N | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 16 | A mixture of 4-(diethoxyphosphoryl)benzoic acid (commercially available, 50 mg, 0.194 mmol), EDCI (44.6 mg, 0.233 mmol), HOBT (31.5 mg, 0.233 mmol) and tert-butyl [2-amino-4-(2-thienyl)phenyl]carbamate (67.7 mg, 0.233 mmol) were taken into DMF (0.58 mL) and stirred for 16 h. Approximately 5 mL of TFA was added to the m... | CCOP(=O)(OCC)c1ccc(C(=O)Nc2cc(-c3cccs3)ccc2N)cc1 | null | null | null |
930,451 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]([OH:23])=[O:22])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH2:30](Cl)Cl>>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH:20]([C:24]3[CH:25]=[CH:26][CH... | ClCCl | O=C(O)C(c1ccccc1)C1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 8 | Thionyl chloride (0.01 mol) was added to a mixture of intermediate (16) (0.0029 mol) in DCM (10 ml). The mixture was stirred overnight and then the solvent was evaporated. The residue was dissolved in DCM (10 ml). Methanol (10 ml) was added. The mixture was allowed to stand for 4 hours, then poured out into a NaHCO3 so... | COC(=O)C(c1ccccc1)C1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | null |
1,403,280 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | Cl[C:2]1[N:7]=[C:6]2[S:8][C:9]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:21](=[O:33])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=4)[CH:17]=[CH:16][C:15]=3[CH3:34])=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:35][NH2:36].CO>CC(O)CC>[C:31]([C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH... | CN | Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1NC(=O)c1cc2ncc(Cl)nc2s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCC(C)O | null | null | null | null | null | null | null | null | null | null | null | A solution of 3-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 95 (0.049 mmol, 24 mg) and methylamine 33% in MeOH (0.049 mmol, 500 μL, 4.61 mg) in butan-2-ol (500 μL) was stirred at 150° C. for 5 h. The reaction mixture was concentrated under reduced pressure and purifi... | CNc1cnc2cc(C(=O)Nc3cc(NC(=O)c4cccc(C(C)(C)C#N)c4)ccc3C)sc2n1 | null | 12 | null |
1,589,386 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14](O)=[O:15])=[CH:11][CH:12]=2)[C@H:7]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2].[NH3:31]>>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH2:31])=[O:15])=[CH:11][CH:12]=2)[C@H:... | CC(=O)N1c2ccc(C(=O)O)cc2[C@H](Nc2ccc(N3CCOCC3)cc2)C[C@@H]1C | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | [Step 1] Reactions and treatments were carried out in the same manner as in Example 118, using 122.8 mg of (2S,4R)-1-acetyl-2-methyl-4-[(4-morpholinophenyl)amino]-1,2,3,4-tetrahydroquinoline-6-carboxylic acid instead of (2S,4R)-1-acetyl-2-methyl-4-(4-morpholinophenoxy)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, and... | CC(=O)N1c2ccc(C(N)=O)cc2[C@H](Nc2ccc(N3CCOCC3)cc2)C[C@@H]1C | null | 100 | null |
1,013,619 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH:11]=O)[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[S:13]1[CH2:17][C:16](=[O:18])[NH:15][C:14]1=[O:19]>>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH:11]=[C:17]3[S:13][C:14](=[O:19])[NH:15][C:16]3=[O:18])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1 | O=C1CSC(=O)N1 | Cc1coc2ccc(C=O)cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the general method as outlined in Example 1, starting from 3-Methyl-benzofuran-5-carbaldehyde (intermediate 57) and 1,3-thiazolidine-2,4-dione, the title compound was obtained. | Cc1coc2ccc(C=C3SC(=O)NC3=O)cc12 | null | null | null |
47,915 | ord_dataset-b43eb0158fd54801957aaa07bbdf3057 | null | 1978-01-01T00:11:00 | true | [C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17]>C(=S)=S>[CH2:14]([C:18]1[CH:23]=[CH:22][C:21]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17] | CCCCc1ccccc1 | O=C(Cl)c1ccccc1 | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | S=C=S | null | null | null | null | null | null | null | null | null | null | null | 18 | A 2.8 g (0.02 mole) of benzoic acid chloride was dissolved in 30 ml of carbon disulfide and then, 4.0 g (0.03 mole) of anhydrous aluminum chloride was added to the solution. A 2.68 g (0.02 mole) of n-butyl benzene was further added to the mixture with stirring, and the reaction was carried out at room temperature for 1... | CCCCc1ccc(C(=O)c2ccccc2)cc1 | null | 96.5 | null |
192,802 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | [Cl:1][CH:2]([C:6]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[O:7])[CH2:3][CH2:4]Cl>C(O)(C)(C)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:2]2([Cl:1])[CH2:4][CH2:3]2)=[O:7])=[CH:9][CH:10]=1 | O=C(c1ccc(F)cc1)C(Cl)CCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | 40 | 2 | 233 g (0.99 mol) of 4-fluorophenyl 1,3-dichloropropyl ketone are dissolved in 300 ml of tert.-butanol and 135 g of potassium tert.-butylate are added in portions. The mixture is substantially stirred at 40° C. for 2 hours and concentrated in vacuo. The residue is taken up in methylene chloride and water. The organic ph... | O=C(c1ccc(F)cc1)C1(Cl)CC1 | null | 73.7 | null |
1,749,237 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:20]=3[N:19]=[C:18]([O:21][C@@H:22]3[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]3)[CH:17]=[CH:16]4)[NH:10][C:6]=2[CH2:5][CH2:4][NH:3]1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=... | CC(C)(C)OC(=O)N1CCC[C@@H](Oc2ccc3cccc(-c4cc5c([nH]4)CCNC5=O)c3n2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.33 | To a solution of (R)-tert-butyl 3-((8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinolin-2-yl)oxy)piperidine-1-carboxylate (117 mg, 0.25 mmol) in DCM (3.0 mL) at 0° C. was added TFA (0.5 mL, 6.73 mmol). The reaction was stirred at RT for 20 min. The solution was concentrated, the residue was dissolved in ... | O=C1NCCc2[nH]c(-c3cccc4ccc(O[C@@H]5CCCNC5)nc34)cc21 | null | 13.2 | null |
897,110 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=O)[C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.[F:15][C:16]([F:38])([F:37])[C:17]1[CH:18]=[C:19]([CH2:23][CH2:24][NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Si:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)[CH:20]=[CH:21][CH:22]=1>>[F:38][C:16]([F:15])([F:37])[C:17]1[CH... | C[Si](C)(C)c1ccc(CNCCc2cccc(C(F)(F)F)c2)cc1 | O=C(O)c1c(F)c(Cl)cc2cc[nH]c12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5-Chloro-6-fluoro-1H-indole-7-carboxylic acid [2-(3-trifluoromethyl-phenyl)-ethyl]-(4-trimethylsilanyl-benzyl)-amide was prepared in analogy to example 1 from 5-chloro-6-fluoro-1H-indole-7-carboxylic acid and [2-(3-trifluoromethyl-phenyl)-ethyl]-(4-trimethylsilanyl-benzyl)-amine. MS (ISP) 547.3/549.4 (100/33) (M+H)+. | C[Si](C)(C)c1ccc(CN(CCc2cccc(C(F)(F)F)c2)C(=O)c2c(F)c(Cl)cc3cc[nH]c23)cc1 | null | null | null |
1,452,589 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH2:11])[C:3]=1[NH2:12].[CH:13]1([C:16](O)=O)[CH2:15][CH2:14]1.Cl.[OH-].[Na+]>>[Br:1][C:2]1[C:3]2[N:12]=[C:16]([CH:13]3[CH2:15][CH2:14]3)[NH:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1 | Nc1cc([N+](=O)[O-])cc(Br)c1N | O=C(O)C1CC1 | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 105 | null | In a 250 mL round-bottom flask a mixture of 3-bromo-5-nitrobenzene-1,2-diamine (4 g, 17.24 mmol) and cyclopropanecarboxylic acid (14.06 ml, 155 mmol) in 3M HCl (40 ml, 120 mmol) was heated to 105° C. for 5 days. The mixture was allowed to cool to room temperature and was poured into chilled 5M NaOH (25 ml, 125 mmol) so... | O=[N+]([O-])c1cc(Br)c2nc(C3CC3)[nH]c2c1 | null | 88.4 | null |
664,417 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | [C:1]([O:5][CH2:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[C:1]([O:5][CH2:6][CH:7]([OH:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])([CH3:3])([CH3:4])[CH3:2] | CCOC(=O)CC(=O)COC(C)(C)C | null | null | [BH4-] | [Na+] | 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 | 1 | Ethyl 4-t-butoxyacetoacetate (20.0 g) synthesized according to the method described in Heterocycles 26, 2841 (1987) was dissolved in methanol (150 mL) and sodium borohydride (1.68 g) was added at a temperature of from 5° C. to 15° C. The mixture was stirred for 1 hr and water (100 mL) was added. The solvent was mostly ... | CCOC(=O)CC(O)COC(C)(C)C | null | 83.7 | null |
1,144,561 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [NH2:1][C:2]1[C:3]2[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=2[Se:5][C:6]=1[C:7]([NH2:9])=[O:8].[N:14]([O-])=O.[Na+]>S(=O)(=O)(O)O>[N:1]1[C:2]2[C:3]3[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=3[Se:5][C:6]=2[C:7](=[O:8])[NH:9][N:14]=1 | O=N[O-] | NC(=O)c1[se]c2ccccc2c1N | null | O=S(=O)(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 | 0 | 2 | To an ice cold (0° C.) solution of 3-aminobenzo[b]selenophene-2-carboxamide (1.0 g, 4.16 mmol) in concentrated sulfuric acid (25 mL) was added a cold (0° C.) solution of sodium nitrite (0.316 g, 4.58 mmol) in concentrated sulfuric acid (10 mL) for 10 min (while adding, the temperature should keep between −5-0° C.). Aft... | O=c1[nH]nnc2c1[se]c1ccccc12 | null | 19.2 | null |
259,512 | ord_dataset-b17fdf55f5f945a48d47a588fc255573 | null | 1992-01-01T00:12:00 | true | Cl[CH2:2][C:3]([C:5]1[S:26][C:8]2[S:9][CH2:10][CH2:11][C:12]3[C:13](=[N:14][N:15]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=4)[C:16](=[O:18])[CH:17]=3)[C:7]=2[CH:6]=1)=[O:4].[C:27]([O-:30])(=[O:29])[CH3:28].[K+].O>C(O)(=O)C>[C:27]([O:30][CH2:2][C:3]([C:5]1[S:26][C:8]2[S:9][CH2:10][CH2:11][C:12]3[C:13](=[N:14... | CC(=O)[O-] | O=C(CCl)c1cc2c(s1)SCCc1cc(=O)n(-c3ccc(Cl)cc3)nc1-2 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | To a suspension of 3.2 g of 9-chloroacetyl-2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one obtained in Example 47 in 40 ml of acetic acid is added 6.0 g of potassium acetate and the mixture is refluxed under heating for 3 hours with stirring. After cooling, to the mixture is added wate... | CC(=O)OCC(=O)c1cc2c(s1)SCCc1cc(=O)n(-c3ccc(Cl)cc3)nc1-2 | null | null | null |
1,025,359 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH:14]([C:19](=O)[CH2:20][CH3:21])[C:15](=O)[CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:24][NH2:25]>C(O)C>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][C:14]1[C:19]([CH2:20][CH3:21])=[N:24][NH:25][C:15]=1[CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH... | CCC(=O)C(Cc1nccn1Cc1ccccc1)C(=O)CC | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | To a solution of 140 mg (0.47 mmol) 4-(1-benzyl-1H-imidazol-2-ylmethyl)-heptane-3,5-dione in 1.5 ml ethanol was added a solution of 24 mg (0.48 mmol) hydrazine monohydrate in 0.5 ml ethanol and the mixture heated to reflux for 10 min. The reaction mixture was evaporated under reduced pressure, the residue dissolved in ... | CCc1n[nH]c(CC)c1Cc1nccn1Cc1ccccc1 | null | null | null |
24,998 | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | null | 1977-01-01T00:05:00 | true | [C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[N:24]=[C:25]=[S:26])(=[O:3])[CH3:2].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C(C)=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](... | NCc1ccccc1 | CC(=O)OC[C@H]1OC(N=C=S)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | 0.5 | To 10 ml of anhydrous xylene were added 390 mg (1 mmol) of 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl isothiocyanate and then slowly added 110 mg (1 mmol) of benzylamine (MW 107) under ice-cooling and stirring over 30 minutes. The mixture was then stirred at room temperature for 1.5 hours, during which crystals were depos... | CC(=O)OC[C@H]1O[C@@H](NC(=S)NCc2ccccc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | null |
404 | ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad | null | 1976-01-01T00:01:00 | true | Cl.[NH2:2][C:3]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24]Br>C(O)C>[Cl:19][C:15]1[CH:14]=[C:13]([C:11]2([OH:12])[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]3[CH2:21][CH2:22][CH2:23][CH2:24][N:2]=[C:3]23)[CH... | NC1=Nc2ccccc2C1(O)c1cccc(Cl)c1 | BrCCCCBr | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 2-Amino-3-(m-chlorophenyl)-3H-indol-3-ol hydrochloride (8.66 g) was converted to its oily base then heated under reflux with 1,4-dibromobutane (6.35 g) in ethanol (20 ml) for 4 hours. On cooling the title compound was obtained as its hydrobromide salt (2.41 g) m.p. 270°-275° C (decomp.) after recrystallization from met... | OC1(c2cccc(Cl)c2)C2=NCCCCN2c2ccccc21 | null | null | null |
1,115,150 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[C:11](=S)[NH:10][C@@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[Br:20])[CH2:8][C:6]=2[N:7]=1.[CH3:22][C:23]1([CH3:31])[O:27][C@@H:26]([CH2:28][O:29][NH2:30])[CH2:25][O:24]1>O1CCOCC1>[CH3:22][C:23]1([CH3:31])[O:27][C@@H:26]([CH2:28][O:29]/[N:30]=[C:11]2\[NH:10][C@@H... | Cc1nc(N)nc2c1C(=S)N[C@@H](c1ccc(F)cc1Br)C2 | CC1(C)OC[C@H](CON)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 100 | null | A 4 mL vial charged with (R)-2-amino-7-(2-bromo-4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-pyrido[4,3-d]pyrimidine-5-thione (31I (Example 31), 107 mg, 0.28 mmol), (R)—O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine (247 mg, 1.68 mmol), and dioxane (2 mL) was heated to 100° C. for 12 h. The crude mixture was purif... | Cc1nc(N)nc2c1/C(=N/OC[C@H]1COC(C)(C)O1)N[C@@H](c1ccc(F)cc1Br)C2 | null | 30 | null |
169,235 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[C:15](O)(=O)/[CH:16]=[CH:17]/[CH3:18].N>O>[CH:16]([C:15]1[NH:11][C:10]2[CH:9]=[C:8]3[NH:7][C:6](=[O:12])[C:5]([CH3:14])([CH3:13])[C:4]3=[CH:3][C:2]=2[N:1]=1)=[CH:17][CH3:18] | CC1(C)C(=O)Nc2cc(N)c(N)cc21 | C/C=C/C(=O)O | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | Analogously to Example 11, 0.95 g. 5,6-diamino-3,3-dimethylindolin-2-one and 0.43 g. crotonic acid are heated with 10 ml. polyphosphoric acid for 30 minutes at 170° C. (bath temperature). The cooled reaction mixture is dissolved in 40 ml. water and neutralised with concentrated aqueous ammonia solution. Insoluble mater... | CC=Cc1nc2cc3c(cc2[nH]1)NC(=O)C3(C)C | null | null | null |
371,697 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:23]OS(C)(=O)=O)[C:13]([NH:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH:12]([CH2:23][N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[C... | c1c[nH]cn1 | COC(=O)CCCNC(=O)C(COS(C)(=O)=O)NS(=O)(=O)c1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The procedure described in Example 79 was repeated, except that (RS)-2-(4-chlorobenzenesulfonylamino)-3-methanesulfonyloxy-N-(3-methoxycarbonylpropyl)propanamide (107.6 mg) was reacted with imidazole to obtain the desired (RS)-2-(4-chlorobenzenesulfonylamino)-3-(1H-imidazol-1-yl)-N-(3-methoxycarbonylpropyl)propanamide ... | COC(=O)CCCNC(=O)C(Cn1ccnc1)NS(=O)(=O)c1ccc(Cl)cc1 | null | null | null |
386,707 | ord_dataset-d330662edaed408d950898172aba7a4c | null | 1997-01-01T00:12:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([CH3:13])([CH3:12])[C:6]=2[CH:14]=1.I[CH2:16][CH2:17][CH2:18][CH3:19]>[Cu]I.O1CCCC1>[CH2:16]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([CH3:13])([CH3:12])[C:6]=2[CH:14]=1)[CH2:17][CH2:18][CH3:19] | CCCCI | CC1(C)CCCCc2ccc(Br)cc21 | null | [Cu]I | 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 | -15 | null | The corresponding Grignard compound was prepared under argon from 304 mg of Mg shavings and 2.50 g of 2-bromo-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene in 25 ml of abs. tetrahydrofuran. After cooling to -15° C. 206 mg of CuI and 1.78 ml of 1-iodobutane were added in succession. The mixture was left to react ... | CCCCc1ccc2c(c1)C(C)(C)CCCC2 | null | null | null |
1,174,244 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][CH:20]=2)=[N:16][CH:17]=1.[BH4-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH:11][C:12]1[C... | CCOC(=O)CCc1ccc(Oc2ccc(N)cn2)cc1 | O=Cc1ccc(Cl)c(Cl)c1 | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 40 | 2 | A solution of 3,4-dichlorobenzaldehyde (1.28 g, 7.3 mmol) was added to a solution of ethyl 3-[4-(5-aminopyridin-2-yloxy)phenyl]propionate (2.1 g, 7.3 mmol) in ethanol (20 mL), and the resulting solution was stirred for 2 hours at 40° C. To the resulting reaction solution was added sodium borohydride (0.55 g, 15.7 mmol)... | CCOC(=O)CCc1ccc(Oc2ccc(NCc3ccc(Cl)c(Cl)c3)cn2)cc1 | null | null | null |
947,492 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [F:1][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=O.P(Br)(Br)[Br:21].C(=O)(O)[O-].[Na+]>CN(C=O)C.O>[Br:21][C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[C:4]([O:18][CH3:19])[CH:5]=2)[N:10]=[CH:9][C:8]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13] | CCOC(=O)c1c[nH]c2c(F)cc(OC)cc2c1=O | BrP(Br)Br | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of ethyl 8-fluoro-6-(methoxy)-4-oxo-1,4-dihydro-3-quinolinecarboxylate (12 g, 45 mmol) in DMF (56 ml) was added dropwise phosphorus tribromide (4.5 ml, 47 mmol) over fifteen minutes (slightly exothermic). The reaction was held at 0° C., with an ice bath, for one hour and allowed to warm to room temperatur... | CCOC(=O)c1cnc2c(F)cc(OC)cc2c1Br | null | 82.6 | null |
1,080,213 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [OH-].[Na+].CO.[C:5]([NH:13][C:14]1[CH:23]=[C:22]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18]C)=[O:17])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1>[C:5]([NH:13][C:14]1[CH:23]=[C:22]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]... | COC(=O)c1ccc(SCc2ccccc2)cc1NC(=O)c1ccccc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 18 | 0.43 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise to a mixed solution of 1.5 mL of methanol and 1.5 mL of tetrahydrofuran containing 0.16 g of methyl 2-(benzamido)-4-(benzylthio)benzoate while ice-cooled and stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and w... | O=C(Nc1cc(SCc2ccccc2)ccc1C(=O)O)c1ccccc1 | null | null | null |
98,672 | ord_dataset-b37811c5ed724c3b844cc4d2b5640398 | null | 1982-01-01T00:09:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]=[C:13]=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[C:17](=[O:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=1>CN(C)C(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([N:20]1[CH:21]=[C:16]([F:15])[C:17](=[O:23])[NH:18][C:19]1=[O:22])=[O... | CC(C)(C)OC(=O)NCCCN=C=O | O=c1[nH]cc(F)c(=O)[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 3 | To the above solution of 3-t-butoxycarbonylaminopropyl isocyanate was added a solution of 5-fluorouracil (2.60 g.) in N,N-dimethylacetamide (20 ml.) at 80° C. and stirred for further 3 hours at the same temperature. The resultant mixture was diluted with ethyl acetate (200 ml.), washed with water (each 30 ml., 3 times)... | CC(C)(C)OC(=O)NCCCNC(=O)n1cc(F)c(=O)[nH]c1=O | null | null | null |
1,497,317 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[C:14]4[C@:19]([C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=5)=[O:22])([CH2:20][C:11]=3[CH:10]=[N:9]2)[CH2:18][NH:17][CH2:16][CH2:15]4)=[CH:4][CH:3]=1.ClCCl.[F:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1.C(N(C(C)C)CC)(C)C>>[F:1][C... | O=S(=O)(Cl)c1ccc(F)cc1 | O=C(c1ccccn1)[C@@]12CNCCC1=Cc1c(cnn1-c1ccc(F)cc1)C2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | null | 1.25 | A solution of (R)-(1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinolin-4a-yl)(pyridin-2-yl)methanone in dichloromethane (2.5 ml) (2.7 mL, ˜0.2 mmol) containing disiopropylethylamine (174 μL, 1 mmol) was added to 4-fluoro-phenyl sulfonyl chloride (48 mg, 0.25 mmol) and diisopropylethylamine (100 μL, ... | O=C(c1ccccn1)[C@]12Cc3cnn(-c4ccc(F)cc4)c3C=C1CCN(S(=O)(=O)c1ccc(F)cc1)C2 | null | null | null |
1,739,846 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)(=[O:17])=[O:16])=[CH:11][C:10]=2[C:24]#[N:25])=[C:4]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH:3]=1.[F:32][C:33]1[C:38](B(O)O)=[CH:37][CH:36]=[C:35]([F:42])[N:34]=1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C)C... | N#Cc1cc(S(=O)(=O)Nc2nccs2)ccc1Oc1cnc(Cl)cc1-c1ccncc1 | OB(O)c1ccc(F)nc1F | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | 0.17 | 10 mg (0.02 mmol) of 4-((6-chloro-[4,4′-bipyridin]-3-yl)oxy)-3-cyano-N-(thiazol-2-yl)benzenesulfonamide was dissolved in 3 mL of N,N-dimethylformamide, and 5 mg (0.03 mmol) of (2,6-difluoropyridin-3-yl)boronic acid was added thereto, and then 2.4 mg (10 mol %) of Pd(PPh3)4, 6.7 mg (0.6 mmol) of Na2CO3, and 1 mL of H2O ... | N#Cc1cc(S(=O)(=O)Nc2nccs2)ccc1Oc1cnc(-c2ccc(F)nc2F)cc1-c1ccncc1 | null | 18.2 | null |
1,171,991 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[CH:21](Br)([CH3:23])[CH3:22].C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:14][CH:15]1[CH2:16][CH2:17][N:18]([... | CC(C)Br | Cc1c[nH]c(=O)c2cc(F)c(OC3CCNCC3)cc12 | null | null | 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 | null | null | By alkylation of 50 mg of 7-fluoro-4-methyl-6-(piperidin-4-yloxy)-2H-isoquinolin-1-one (22) with isopropylbromide in the presence of triethylamine in DMF at 60° C. 31 mg of 7-Fluoro-6-(1-isopropyl-piperidin-4-yloxy)-4-methyl-2H-isoquinolin-1-one were obtained. | Cc1c[nH]c(=O)c2cc(F)c(OC3CCN(C(C)C)CC3)cc12 | null | null | null |
1,593,393 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]([O:5][C:6]([N:8]1[C@H:20]([C:21]([OH:23])=[O:22])[CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C@H:20]([C:21]([OH:23])=[O:22])[CH2:19... | Fc1ccc(CBr)cc1 | CC(C)(C)OC(=O)N1Cc2[nH]c3ccccc3c2C[C@H]1C(=O)O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 1 | The acid 2 (20.0 g, 63.2 mmol) in DMF (630 mL) was degassed and the flask was cooled in ice water bath. NaH (60% in mineral oil; 7.8 g, 196.0 mmol) was slowly added portionwise over 45 min at 0° C. and stirred for 1 hr. 4-fluorobenzyl bromide (8.7 mL, 69.5 mmol) was added dropwise over 45 min at 0° C. and stirred for 1... | CC(C)(C)OC(=O)N1Cc2c(c3ccccc3n2Cc2ccc(F)cc2)C[C@H]1C(=O)O | null | 72.7 | null |
245,085 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | C(N(CC)CC)C.Cl.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=O.Cl.[C:20]1([C:26]2([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:34]3[CH:30]([CH2:31][NH:32][CH2:33]3)[C:29](=[O:35])[CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:36]1([C:26]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH... | O=C(O)Cc1ccccn1 | O=C1CCC(c2ccccc2)(c2ccccc2)C2CNCC12 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | 0.25 | Triethylamine (1.4 cc) is added to a suspension of 2-(2-pyridyl)acetic acid hydrochloride (1.73 g) in dry dichloromethane (30 cc). The solution is cooled to +5° C. and then treated with N,N'-carbonyldiimidazole (1.62 g). The mixture is stirred for 15 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhyd... | O=C1CCC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccccn3)CC12 | null | 39.1 | null |
932,741 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [CH3:1][C:2]([NH:5][S:6]([C:9]1[C:10]([F:19])=[CH:11][C:12]([F:18])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)(=[O:8])=[O:7])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.ClC1C(C([N:62]2[CH2:67][CH2:66][C:65]([C:88]3[CH:93]=[CH:92][CH:91]=[C:90]([F:94])[CH:89]=3)([CH2:68][CH2:69][N:70... | CC(C)(C)NS(=O)(=O)c1cc(C(=O)O)c(F)cc1F | CNS(=O)(=O)c1ccc(Cl)c(C(=O)N2CCC(CCN3C4CCC3CC(n3c(C)nc5ccccc53)C4)(c3cccc(F)c3)CC2)c1Cl | 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 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from a mixture of 5-{[(1,1-dimethylethyl)amino]sulfonyl}-2,4-difluorobenzoic acid 882-3b 1-(8-{2-[4-(3-fluorophenyl)-4-piperidinyl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole (100 mg, 0.16 mmol, 1 equiv), DIEA (117 μL, 0.66 mmol, 4 equiv) and HATU (62 mg, 0.16 mmol, 1 equiv) following the gen... | Cc1nc2ccccc2n1C1CC2CCC(C1)N2CCC1(c2cccc(F)c2)CCN(C(=O)c2cc(S(=O)(=O)NC(C)(C)C)c(F)cc2F)CC1 | null | 40 | null |
1,504,430 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | Br[C:2]([CH3:16])([CH3:15])[C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(COC)OC>[C:7]1([CH3:14])[CH:8]=[C:9]([CH3:13])[CH:10]=[C:11]([CH3:12])[C:6]=1[NH:5][CH2:3][C:2]([CH3:16])([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:15] | Cc1cc(C)c(NC(=O)C(C)(C)Br)c(C)c1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of the amide (100 mg, 0.337 mmol) in dry dimethoxyethane (2 ml) was added lithium aluminum hydride (80 mg, 2.1 mmol), and the mixture was refluxed for 1 day. After cooling to room temperature, the reaction was quenched by adding H2O (0.08 ml), 15% aqueous NaOH (0.08 ml), and H2O (0.24 ml) successively. The w... | Cc1cc(C)c(NCC(C)(C)Nc2ccccc2)c(C)c1 | null | null | null |
1,702,135 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([F:17])[CH:3]=1.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1B(O)O>>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[C:7]([CH3:16])[... | OB(O)c1ccc(F)cc1F | Cc1c2n(c3c(Br)cc(F)cc13)CCNC2=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, white solid (32 mg, 39%), MS (ISP) m/z=331.4 [(M+H)+], mp 204° C., was prepared in accordance with the general method of example 1 from 6-bromo-8-fluoro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (intermediate 14) (74.3 mg, 0.25 mmol) and commercially available 2,4-difluoro-phenylboronic ac... | Cc1c2n(c3c(-c4ccc(F)cc4F)cc(F)cc13)CCNC2=O | null | null | null |
857,024 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH:10]([CH2:19][CH2:20]Cl)[C:9]2=[O:22])=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=1.C(N(CC)CC)C>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:... | Fc1ccc(S)cc1 | O=C1C(CCCl)C(c2ccc(O)cc2)N1c1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 20 | To a stirring solution of 1-(4-fluorophenyl)-3-(2-chloroethyl)-4-(4-hydroxyphenyl)azetidin-2-one (Method 12; 0.750 g, 2.35 mmol) in MeCN (10 ml) was added 4-fluorothiophenol (0.500 ml, 4.60 mmol) and triethylamine (0.500 ml, 3.59 mmol) at room temperature. After 20 hours there were still start materiel left (approximat... | O=C1C(CCSc2ccc(F)cc2)C(c2ccc(O)cc2)N1c1ccc(F)cc1 | null | null | null |
528,358 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | CN(C=O)C.[H-].[Na+].[C:8]1([CH3:15])[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.[NH2:16][C:17]1[N:25]=[C:24](Cl)[N:23]=[C:22]2[C:18]=1[N:19]=[CH:20][N:21]2[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>[Cl-].[Na+].O>[NH2:16][C:17]1[N:25]=[C:24]([S:14][C:11]2[CH:12]=[CH:13][C:8]([CH3:15])=[CH:9][CH:10]=2)[N:2... | Nc1nc(Cl)nc2c1ncn2Cc1ccccc1 | Cc1ccc(S)cc1 | null | [Cl-] | [H-] | [Na+] | 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 | To DMF suspension (10 ml) containing sodium hydride (300 mg, 7.5 mmol, 60% in mineral oil) were added p-toluenethiol (1.9 g, 15 mmol) and 6-amino-9-benzyl-2-chloropurine (100 mg, 0.39 mmol) in order. The mixture was stirred under heating at 100° C. for 3 hours. Brine was added thereto and the mixture was extracted with... | Cc1ccc(Sc2nc(N)c3ncn(Cc4ccccc4)c3n2)cc1 | null | 91.5 | null |
1,245,445 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | I[C:2]1[C:7]([NH2:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[C:4]([CH3:12])[CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=1)#[CH:14]>>[CH3:12][C:4]1[CH:3]=[C:2]2[C:7](=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=1)[NH:8][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=1)=[CH:14]2 | C#Cc1cccc(C)n1 | Cc1cc(I)c(N)c([N+](=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 | 6-Iodo-4-methyl-2-nitroaniline (500 mg, 1.8 mmol) and 2-ethinyl-6-methylpyridine (210 mg, 1.8 mmol) were reacted according to the same procedure as Preparation 19 to give the title compound (170 mg, Yield 35%). | Cc1cc([N+](=O)[O-])c2[nH]c(-c3cccc(C)n3)cc2c1 | null | 35.3 | null |
140,912 | ord_dataset-343f84c5bd164b25aeae96e1d828e768 | null | 1986-01-01T00:03:00 | true | Cl.[NH2:2][C:3]1[S:16][C:6]2[CH2:7][CH2:8][N:9]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:10][CH2:11][C:5]=2[CH:4]=1.[S-:17][C:18]#[N:19].[K+].BrBr>>[NH2:19][C:18]1[S:17][C:4]2[C:5]3[CH2:11][CH2:10][N:9]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:8][CH2:7][C:6]=3[S:16][C:3]=2[N:2]=1 | N#C[S-] | CCC(=O)N1CCc2cc(N)sc2CC1 | null | BrBr | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared from 2-amino-6-propionyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine hydrochloride, potassium thiocyanate and bromine analogous to Example 1. | CCC(=O)N1CCc2sc3nc(N)sc3c2CC1 | null | null | null |
383,567 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [NH2:1][C@@H:2]([CH2:21][C:22]1[N:23]=[CH:24][N:25]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=1)[C:3]([NH:5][C@@H:6]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C@@H:7]([OH:13])[C@H:8]([CH:1... | N[C@@H](Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)C1CC1 | O=C(O)c1nc2ccccc2[nH]1 | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)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 | CC#N | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 20 | A mixture of 355 mg (0.58 mmol) of (S)-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-tritylimidazole-4-propionamide, 95 mg (0.58 mmol) of benzimidazole-2-carboxylic acid [Chem. Ber. 45, 3489 (1912)], 256 mg (0.58 mmol) of BOP and 0.12 ml (0.58 mmol) of Hunig base in 50 ml of acetonitri... | O=C(N[C@@H](Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)C1CC1)c1nc2ccccc2[nH]1 | null | 87 | null |
500,049 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [BH4-].[Na+].[CH2:3]([C:5]1[S:6][C:7]2[CH:14]=[CH:13][C:12]3[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:11]=3[C:10](=[O:20])[C:8]=2[N:9]=1)[CH3:4]>ClCCl.C(O)C>[CH2:3]([C:5]1[S:6][C:7]2[CH:14]=[CH:13][C:12]3[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:11]=3[CH:10]([OH:20])[C:8]=2[N:9]=1)[CH3:4] | CCc1nc2c(=O)c3ccc(C)cc3ccc2s1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCO | null | null | null | null | null | null | null | null | null | 25 | 2.5 | Sodium borohydride (78 mg) was added to a stirred solution of the product from step (ii) (0.87 g) in dichloromethane (4 ml) and ethanol (16 ml) at 5° C. The reaction mixture was stirred for 2.5 h, warmed to room temperature and left for 2 h before a further 200 mg of sodium borohydride was added. The reaction mixture w... | CCc1nc2c(s1)C=Cc1cc(C)ccc1C2O | null | null | null |
847,978 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1>C(#N)C>[Br:22][C:10]1[C:11]([NH2:14])=[N:12][CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:9]=1 | O=C1CCC(=O)N1Br | Nc1ccc(-c2ccc(Cl)cc2)cn1 | 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 | null | null | Prepared from crude 5-(4-chloro-phenyl)-pyridin-2-ylamine (example C.27 step 1) (ca. 50 mmol) in acetonitrile (100 mL) and NBS (9.34 g, 53 mmol) as described in example C.25 step 2. Obtained the crude 3-bromo-5-(4-chloro-phenyl)-pyridin-2-ylamine a dark brown solid (76% pure). | Nc1ncc(-c2ccc(Cl)cc2)cc1Br | null | null | null |
1,644,268 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [C:1]([C:4]1[C:5]([OH:28])=[C:6]([C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=1)[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)(=[O:3])[CH3:2].[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:29]([O:28][C:5]1[C:4]([C:1](=[O:3])[CH3:2]... | CC(=O)OC(C)=O | COc1cc(C(C)=O)c(O)c(CN2CCN(C(=O)OC(C)(C)C)CC2)c1OC | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 15 | A solution of tert-butyl 4-(3-acetyl-2-hydroxy-5,6-dimethoxybenzyl)piperazine-1-carboxylate (0.20 g, 0.50 mmol) in pyridine (1.0 mL) was successively added with acetic anhydride (1.0 mL) and 4-dimethylaminopyridine (0.010 g), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was added w... | COc1cc(C(C)=O)c(OC(C)=O)c(CN2CCN(C(=O)OC(C)(C)C)CC2)c1OC | null | 70 | null |
1,335,921 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[C:33]([C:38]([O:40][CH3:41])=[O:39])[CH:34]=[CH:35][CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:42])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[ClH:43].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:43].[O... | COC(=O)c1cccc2c1ccc(=O)n2CCN1CCC(N(Cc2ccc3c(c2)OCCO3)C(=O)OC(C)(C)C)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 42 | To 0.2 mL of an ethyl acetate solution containing 9.0 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-methoxycarbonyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 2 mL of 4 mol/L hydrogen chloride/ethyl acetate was added, and stirred at room temperature for 42 hours. The solvent was removed ... | COC(=O)c1cccc2c1ccc(=O)n2CCN1CCC(NCc2ccc3c(c2)OCCO3)CC1 | null | null | null |
1,658,773 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [OH:1][N:2]=[C:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[Cl:11][C:12]1[C:20]([F:21])=[CH:19][C:15]([C:16](O)=O)=[C:14]([F:22])[CH:13]=1.N>>[Cl:11][C:12]1[C:20]([F:21])=[CH:19][C:15]([C:16]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[N:10]=2)=[C:14]([F:22])[CH:13]=1 | NC(=NO)c1cccnc1 | O=C(O)c1cc(F)c(Cl)cc1F | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the procedure of Example 8 using N′-hydroxynicotinimidamide (Aldrich) and 4-chloro-2,5-difluorobenzoic acid (Aldrich). 1H NMR (300 MHz, CD3OD) δ 7.65 (ddd, J=8.0, 4.9, 1.0 Hz, 1H), 7.73 (dd, J=9.7, 5.9 Hz, 1H), 8.18 (dd, J=8.8, 6.1 Hz, 1H), 8.57 (dt, J=8.1, 1.9 Hz, 1H), 8.75... | Fc1cc(-c2nc(-c3cccnc3)no2)c(F)cc1Cl | null | null | null |
1,729,123 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [F:1][C:2]([F:31])([F:30])[C:3]([N:5]([CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)=[O:4].[CH3:32][N:33]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[N:34]1.C(=O)([O-])[O-].[K+].[K+... | CC(C)(C)OC(=O)N1CCC(CN(C(=O)C(F)(F)F)[C@@H]2C[C@H]2c2ccc(I)cc2)CC1 | Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1 | 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 | CC#N | O | null | null | null | null | null | null | null | null | null | 85 | 4 | To a 10-mL microwave tube were added tert-butyl 4-((2,2,2-trifluoro-N-(trans-2-(4-iodophenyl)cyclopropyl)acetamido)methyl)piperidine-1-carboxylate (300 mg, 0.543 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (136 mg, 0.652 mmol), potassium carbonate (263 mg, 1.901 mmol), acetonitrile (2 mL... | Cn1cc(-c2ccc([C@@H]3C[C@H]3N(CC3CCN(C(=O)OC(C)(C)C)CC3)C(=O)C(F)(F)F)cc2)cn1 | null | 43.6 | null |
733,355 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [CH:1]1([C:4]2[C:9]([CH2:10]O)=[C:8]([CH2:12][O:13][CH3:14])[N:7]=[C:6]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:5]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:27])=O>ClCCl>[Cl:27][CH2:10][C:9]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][C:6]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:... | COCc1nc(-c2ccc(C(F)(F)F)cc2)nc(C2CC2)c1CO | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of 1.29 g (3.8 mmol) [4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol in 12 ml dichloromethane was treated with 0.29 ml (3.99 mmol) thionylchloride. After 2 h stirring at RT, the mixture was partitioned between ether and water. The ether-phase was concentrated under reduce... | COCc1nc(-c2ccc(C(F)(F)F)cc2)nc(C2CC2)c1CCl | null | 99.6 | null |
1,150,059 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[O:7][C:6]1=[O:17].[CH3:18][O:19][CH2:20][CH2:21][OH:22]>>[CH3:18][O:19][CH2:20][CH2:21][O:22][C:6]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[O:7][CH2:2][CH2:3][CH2:4]1)=[O:17] | COCCO | O=c1oc2cc([N+](=O)[O-])ccc2n1CCCCl | null | null | null | null | null | null | null | 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-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid 2-methoxy-ethyl ester was prepared from 3-(3-chloro-propyl)-6-nitro-3H-benzoxazol-2-one and 2-methoxyethanol in an analogous manner to Example 1426a. Product isolated as a yellow oil (175 mg, 25%). LCMS (m/e) 297 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 7.8... | COCCOC(=O)N1CCCOc2cc([N+](=O)[O-])ccc21 | null | null | null |
129,773 | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | null | 1985-01-01T00:05:00 | true | [CH:1]([NH:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=2)[C:7](=[O:15])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]1)=O.[C:21](=O)([O-])[O-:22].[K+].[K+].CI>CN(C)C=O>[CH:21]([CH2:1][NH:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=2)[C:7](=[O:15])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[... | O=C([O-])[O-] | CCOC(=O)c1cn(NC=O)c2nc(C)ccc2c1=O | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 0.5 | Ethyl 1-(formylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate (11.8 g, 0.043 m) was added to a stirred mixture of 20.3 g (0.136 m) of anhydrous, milled potassium carbonate and 103 ml of dimethylformamide. The mixture was stirred for 30 minutes, and 20.3 ml (0.33 m) of methyl iodide was then added. Th... | CCOC(=O)c1cn(NCC=O)c2nc(C)ccc2c1=O | null | null | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.