Dimethylformamide → 2,3-dihydro-1H-1-benzazepine-4-carboxamide dihydrochloride

HRID 586908ノート

反応式

HRID 586908 の反応式
C1(C[N:5]2[C:11]3[CH:12]=[CH:13][C:14](C4C=CC(OCCOCCC)=CC=4)=[CH:15][C:10]=3[CH:9]=[C:8]([C:29]([OH:31])=O)[CH2:7][CH2:6]2)CC1.C(Cl)(=O)C([Cl:35])=O.C[N:39](C=O)C>C1COCC1>[ClH:35].[ClH:35].[NH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]([C:29]([NH2:39])=[O:31])[CH2:7][CH2:6]1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 223290701-cyclopropylmethyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

生成物 1

HCID 867598322,3-dihydro-1H-1-benzazepine-4-carboxamide dihydrochloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In THF (5 ml) was dissolved 1-cyclopropylmethyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.25 g). Under ice-cooling, to the solution were added oxalyl chloride (0.11 ml) and DMF (catalytic amount). The mixture was stirred at room temperature for 1 hour, and the solvent was evaporated under reduced pressure. In THF (25 ml) was dissolved the residue, and the solution was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.14 g) and triethylamine (0.41 ml) in THF (5 ml), under ice-cooling. The mixture was stirred at room temperature overnight under nitrogen atmosphere and the solvent was evaporated under reduced pressure. 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. The solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate/methanol/triethylamine), which was dissolved in ethyl acetate. To the solution was added 4N hydrochloric acid-ethyl acetate, and the solvent was evaporated to give 1-cyclopropylmethyl-7-[4-(2-propoxyethoxy)phenyl]-N-[4-[[N-methyl-N-tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide dihydrochloride (Compound 36) (0.32 g) as pale yellow amorphous.

後処理

  1. temperatureUnder ice-cooling, to the solution
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionIn THF (25 ml) was dissolved the residue
  4. additionthe solution was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.14 g) and triethylamine (0.41 ml) in THF (5 ml), under ice-
  5. temperaturecooling
  6. stirringThe mixture was stirred at room temperature overnight under nitrogen atmosphere
  7. customthe solvent was evaporated under reduced pressure
  8. additionTo the residue was added water
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with water and saturated brine
  11. dry with materialdried with anhydrous magnesium sulfate
  12. customThe solvent was evaporated
  13. customthe residue was purified with silica gel column chromatography (ethyl acetate/methanol/triethylamine), which
  14. dissolutionwas dissolved in ethyl acetate
  15. additionTo the solution was added 4N hydrochloric acid-ethyl acetate
  16. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-96e556dc99b24c93853ac57eae6640ed
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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