Dimethylformamide → 1-methoxycarbonyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide

HRID 586826ノート

反応式

HRID 586826 の反応式
[CH3:1][O:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:28]([OH:30])=O)[CH2:7][CH2:6]1)=[O:4].S(Cl)(Cl)=O.[CH3:35][N:36]([CH:38]=O)[CH3:37]>>[CH3:1][O:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[CH:20][CH:21]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:28]([NH:5][C:11]2[CH:12]=[CH:13][C:14]([CH2:38][N:36]([CH3:35])[CH:37]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:15][CH:10]=2)=[O:30])[CH2:7][CH2:6]1)=[O:4]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 223292091-methoxycarbonyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

生成物 1

HCID 223290211-methoxycarbonyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide

実験手順

In DMF (8 ml) was dissolved 1-methoxycarbonyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.15 g). To the solution was added, under ice-cooling, thionyl chloride (0.07 ml), and the mixture was stirred at room temperature for 30 minutes. Under reduced pressure, the solvent was evaporated, and the residue was suspended in THF (25 ml). The suspension was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.12 g) and triethylamine (0.26 ml) in THF (5 ml), under ice-cooling, and the mixture was stirred under nitrogen atmosphere at room temperature for 4 hours. Under reduced pressure, the solvent was evaporated. To the residue was added water, and the mixture was 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. The residue was purified with silica gel column chromatography (elution solvent: methanol/triethylamine/ethyl acetate) to give crude crystals, which were recrystallized from ethyl acetate/hexane to give 1-methoxycarbonyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide (0.14 g) as colorless crystals.

後処理

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. customUnder reduced pressure, the solvent was evaporated
  4. additionThe suspension was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.12 g) and triethylamine (0.26 ml) in THF (5 ml), under ice-
  5. temperaturecooling
  6. customUnder reduced pressure, the solvent was evaporated
  7. additionTo the residue was added water
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with water and saturated brine
  10. dry with materialdried with anhydrous magnesium sulfate
  11. customthe solvent was evaporated
  12. customThe residue was purified with silica gel column chromatography (elution solvent: methanol/triethylamine/ethyl acetate)
  13. customto give crude crystals, which
  14. customwere recrystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-3ccf28fd92ee465b8e336b5752eaaf20
出典データセット
uspto-grants-2005_08
特許番号
US06936602B1

反応ノート

読み込み中…