Dimethylformamide → HCID 22329305, compound

HRID 586887Notes

Reaction equation

HRID 586887 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:23]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:22][CH2:21][C:20]([C:28](O)=[O:29])=[CH:19][C:18]=3[CH:31]=2)=[CH:10][CH:9]=1)[CH3:2].S(Cl)(Cl)=O.[CH3:36][N:37]([CH:39]=O)[CH3:38]>C1COCC1>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:23]([S:24]([CH3:27])(=[O:25])=[O:26])[CH2:22][CH2:21][C:20]([C:28]([NH:23][C:17]4[CH:18]=[CH:31][C:14]([CH2:39][N:37]([CH3:36])[CH:38]5[CH2:5][CH2:4][O:3][CH2:1][CH2:2]5)=[CH:15][CH:16]=4)=[O:29])=[CH:19][C:18]=3[CH:31]=2)=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22329107HCID 22329107, compound

Product 1

HCID 22329305HCID 22329305, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (5 ml) was dissolved 7-[4-(3-ethoxypropoxy)phenyl]-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.20 g). To the solution were added, under ice-cooling, thionyl chloride (0.06 ml) and DMF (catalytic amount), and the mixture was stirred at room temperature for 2 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in THF (15 ml). The solution was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.11 g) and triethylamine (0.19 ml) in THF (5 ml), under ice-cooling, and the mixture was stirred under nitrogen atmosphere 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-(3-ethoxypropoxy)phenyl)-1-methanesulfonyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 8) (0.22 g) as colorless crystals.

Workup

  1. additionTo the solution were added, under ice-
  2. temperaturecooling
  3. customUnder reduced pressure, the solvent was evaporated
  4. dissolutionthe residue was dissolved in THF (15 ml)
  5. additionThe solution was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.11 g) and triethylamine (0.19 ml) in THF (5 ml), under ice-
  6. temperaturecooling
  7. customUnder reduced pressure, the solvent was evaporated
  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. customto give crude crystals, which
  14. customwere recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2cd9b9fc22524a7881235abaef36a526
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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