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

HRID 586884Notes

Reaction equation

HRID 586884 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH:25]=[O:26])[CH2:23][CH2:22][C:21]([C:27](O)=[O:28])=[CH:20][C:19]=3[CH:30]=2)=[CH:11][CH:10]=1)[CH2:7][CH3:8])[CH3:2].S(Cl)(Cl)=O.[CH3:35][N:36]([CH:38]=O)[CH3:37]>>[CH2:1]([O:3][CH2:4][CH2:5][N:6]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:30]=[CH:19][C:18]3[N:24]([CH:25]=[O:26])[CH2:23][CH2:22][C:21]([C:27]([NH:6][C:9]4[CH:14]=[CH:13][C:12]([CH2:38][N:36]([CH3:35])[CH:37]5[CH2:5][CH2:4][O:3][CH2:1][CH2:2]5)=[CH:11][CH:10]=4)=[O:28])=[CH:20][C:17]=3[CH:16]=2)=[CH:13][CH:14]=1)[CH2:7][CH3:8])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 223288977-[4-[N-(2-ethoxyethyl)-N-ethylamino]phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

Product 1

HCID 223290077-[4-[N-(2-ethoxyethyl)-N-ethylamino]phenyl]-1-formyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

Procedure

In DMF (5 ml) was dissolved 7-[4-[N-(2-ethoxyethyl)-N-ethylamino]phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.2 g). To the solution was added, under ice-cooling, thionyl chloride (0.09 ml), and the mixture was stirred at room temperature for 30 minutes. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in THF (25 ml). The solution was added dropwise a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.20 g) and triethylamine (0.35 ml) in THF (5 ml), under ice-cooling, and the mixture was stirred under nitrogen atmosphere stirred at room temperature overnight. 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 to give crude crystals, which were recrystallized from ethyl acetate/hexane to give 7-[4-[N-(2-ethoxyethyl)-N-ethylamino]phenyl]-1-formyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 5) (0.23 g) as pale yellow crystals.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. customUnder reduced pressure, the solvent was evaporated
  4. dissolutionthe residue was dissolved in THF (25 ml)
  5. additionThe solution was added dropwise a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.20 g) and triethylamine (0.35 ml) in THF (5 ml)
  6. temperatureunder ice-cooling
  7. stirringstirred at room temperature overnight
  8. customUnder reduced pressure, the solvent was evaporated
  9. additionTo the residue was added water
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with water and saturated brine
  12. dry with materialdried with anhydrous magnesium sulfate
  13. customthe solvent was evaporated
  14. customto give crude crystals, which
  15. customwere recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-017d096ac9c3483c9acaef460f7ad3e0
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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