Potassium Carbonate → 7-(4-ethylphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide

HRID 2228245ノート

反応式

HRID 2228245 の反応式
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1.Br[C:14]1[CH:15]=[CH:16][C:17]2[N:23]([CH3:24])[CH2:22][CH2:21][C:20]([C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][N:35]([CH3:42])[CH:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[CH:30][CH:29]=3)=[O:26])=[CH:19][C:18]=2[CH:43]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([C:14]2[CH:15]=[CH:16][C:17]3[N:23]([CH3:24])[CH2:22][CH2:21][C:20]([C:25]([NH:27][C:28]4[CH:29]=[CH:30][C:31]([CH2:34][N:35]([CH3:42])[CH:36]5[CH2:37][CH2:38][O:39][CH2:40][CH2:41]5)=[CH:32][CH:33]=4)=[O:26])=[CH:19][C:18]=3[CH:43]=2)=[CH:4][CH:5]=1)[CH3:10]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 223290367-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamideHCID 867561644-Ethylphenyl borate

生成物 1

HCID 184725257-(4-ethylphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide収率 39.2%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 86587398Ethanol toluene water溶媒

実験手順

In water:ethanol:toluene (1:1:10, 18.0 ml) were dissolved 4-ethylphenyl borate (227 mg) and 7-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]-methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide (611 mg), and to the mixture was added potassium carbonate (418 mg). The mixture was stirred under argon atmosphere for 30 minutes, and to the mixture was added tetrakistriphenylphosphine palladium (59 mg). Under argon atmosphere, the mixture was refluxed for 17 hours, and the mixture was diluted with ethyl acetate (200 ml) and washed with water (50 ml) and saturated brine (50 ml). The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography (75 g, ethyl acetate:ethanol=9:1) and recrystallized from ethanol to give 7-(4-ethylphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide (Compound 307) (252 mg, 39%).

後処理

  1. temperatureUnder argon atmosphere, the mixture was refluxed for 17 hours
  2. washwashed with water (50 ml) and saturated brine (50 ml)
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (75 g, ethyl acetate:ethanol=9:1)
  6. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-35afff30cc294aad902e5a2f329e1575
出典データセット
uspto-grants-2002_07
特許番号
US06413947B1

反応ノート

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