Ethanol → 7-[4-(2-butoxyethoxy)phenyl]-1-cyclopropyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

HRID 586905ノート

反応式

HRID 586905 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH:12]3[CH2:14][CH2:13]3)[CH2:10][CH2:9][C:8]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH3:32])[CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:20][CH:19]=3)=[O:16])=[CH:7][C:6]=2[CH:33]=1.B([O-])([O-])O[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>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)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:46]([O:45][CH2:44][CH2:43][O:42][C:39]1[CH:38]=[CH:37][C:36]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([CH:12]4[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]([C:15]([NH:17][C:18]4[CH:19]=[CH:20][C:21]([CH2:24][N:25]([CH3:32])[CH:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[CH:22][CH:23]=4)=[O:16])=[CH:7][C:6]=3[CH:33]=2)=[CH:41][CH:40]=1)[CH2:47][CH2:48][CH3:49]

参加物

7

反応物 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223290967-bromo-1-cyclopropyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamideHCID 867568154-Butoxyethoxyphenyl borate

生成物 1

HCID 223288907-[4-(2-butoxyethoxy)phenyl]-1-cyclopropyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide収率 45.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

A mixture of 7-bromo-1-cyclopropyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (0.45 g), 4-(2-butoxyethoxy)phenyl borate (0.23 g), 1M potassium carbonate solution (1.5 ml), ethanol (1.5 ml) and toluene (25 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (0.05 g), and the mixture was refluxed for 3 hours under argon atmosphere and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/methanol/triethylamine) to give crude crystals, which were recrystallized to give 7-[4-(2-butoxyethoxy)phenyl]-1-cyclopropyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 31) (0.25 g) as pale yellow crystals.

後処理

  1. temperaturethe mixture was refluxed for 3 hours under argon atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate/methanol/triethylamine)
  7. customto give crude crystals, which
  8. customwere recrystallized

出典と根拠

ORDレコード
ord-99f8a75b2d69429495eed4b9b2860701
出典データセット
uspto-grants-2005_08
特許番号
US06936602B1

反応ノート

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