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Potassium Carbonate → 7-[4-(3-ethoxypropoxy)phenyl]-1-methyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

HRID 586890
ノート
印刷プレビュー

反応式

HRID 586890 の反応式
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15])=[CH:5][CH:4]=1.Br[C:19]1[CH:20]=[CH:21][C:22]2[N:28]([CH3:29])[CH2:27][CH2:26][C:25]([C:30]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([CH2:39][N:40]([CH3:47])[CH:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)=[CH:35][CH:34]=3)=[O:31])=[CH:24][C:23]=2[CH:48]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C1(C)C=CC=CC=1.C(OCC)(=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>[CH2:14]([O:13][CH2:12][CH2:11][CH2:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:19]2[CH:20]=[CH:21][C:22]3[N:28]([CH3:29])[CH2:27][CH2:26][C:25]([C:30]([NH:32][C:33]4[CH:34]=[CH:35][C:36]([CH2:39][N:40]([CH3:47])[CH:41]5[CH2:46][CH2:45][O:44][CH2:43][CH2:42]5)=[CH:37][CH:38]=4)=[O:31])=[CH:24][C:23]=3[CH:48]=2)=[CH:4][CH:5]=1)[CH3:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

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 867568164-(3-Ethoxypropoxy)phenyl borate

生成物 1

HCID 223291327-[4-(3-ethoxypropoxy)phenyl]-1-methyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide収率 66.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 86587398Ethanol toluene water溶媒

実験手順

In a mixture of water ethanol:toluene (1:1:10, v/v, 18.0 ml) were dissolved 4-(3-ethoxypropoxy)phenyl borate (250 mg) and 7-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (450 mg). To the solution was added potassium carbonate (308 mg), and the mixture was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakistriphenylphosphinepalladium (43 mg), and the mixture was refluxed under argon atmosphere for 10 hours. The mixture was diluted with ethyl acetate, and washed with water and saturated brine, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (25 g, ethyl acetate:ethanol:triethylamine=100:10:1) and recrystallized from ethanol/hexane to give 7-[4-(3-ethoxypropoxy)phenyl]-1-methyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 13) (359 mg, 66%) as yellow crystals.

後処理

  1. temperaturethe mixture was refluxed under argon atmosphere for 10 hours
  2. washwashed with water and saturated brine
  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 (25 g, ethyl acetate:ethanol:triethylamine=100:10:1)
  6. customrecrystallized from ethanol/hexane

出典と根拠

ORDレコード
ord-9c03fd21e1a24f22bf29f6f2ef477361
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06936602B1

反応ノート

読み込み中…

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