1-(N-acetylglycyl)-7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide → 7-[4-(2-butoxyethoxy)phenyl]-1-(2-methyloxazol-5-yl)-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

HRID 586910ノート

反応式

HRID 586910 の反応式
[C:1]([NH:4][CH2:5][C:6]([N:8]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=3)=[CH:18][C:13]=2[CH:12]=[C:11]([C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][N:43]([CH3:50])[CH:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:38][CH:37]=2)=[O:34])[CH2:10][CH2:9]1)=O)(=[O:3])[CH3:2]>P(Cl)(Cl)(Cl)=O>[CH2:29]([O:28][CH2:27][CH2:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[CH:16]=[CH:15][C:14]3[N:8]([C:6]4[O:3][C:1]([CH3:2])=[N:4][CH:5]=4)[CH2:9][CH2:10][C:11]([C:33]([NH:35][C:36]4[CH:37]=[CH:38][C:39]([CH2:42][N:43]([CH3:50])[CH:44]5[CH2:45][CH2:46][O:47][CH2:48][CH2:49]5)=[CH:40][CH:41]=4)=[O:34])=[CH:12][C:13]=3[CH:18]=2)=[CH:20][CH:21]=1)[CH2:30][CH2:31][CH3:32]

参加物

3

反応物 1

HCID 223291241-(N-acetylglycyl)-7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

生成物 1

HCID 223292517-[4-(2-butoxyethoxy)phenyl]-1-(2-methyloxazol-5-yl)-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide収率 53.4%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
50 °C

実験手順

In phosphorus oxychloride (25 ml) was dissolved 1-(N-acetylglycyl)-7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (0.5 g). The solution was heated to stir at room temperature for 7 hours and at 50° C. for 2 hours, and the solvent was evaporated. To the residue was added sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified with basic silica gel column chromatography (ethyl acetate/hexane). The resulting crude crystals were recrystallized from ethyl acetate-hexane to give 7-[4-(2-butoxyethoxy)phenyl]-1-(2-methyloxazol-5-yl)-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 44) (0.26 g) as pale yellow crystals.

後処理

  1. temperatureThe solution was heated
  2. customthe solvent was evaporated
  3. additionTo the residue was added sodium hydrogen carbonate solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified with basic silica gel column chromatography (ethyl acetate/hexane)
  9. customThe resulting crude crystals were recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-d760321bfde14a918232e3c63e002ebe
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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