Dimethylformamide → HCID 22329109, compound

HRID 586825Notes

Reaction equation

HRID 586825 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:19]([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:18][CH2:17][C:16]([C:24](O)=[O:25])=[CH:15][C:14]=3[CH:27]=2)=[CH:6][CH:5]=1)[CH3:2].S(Cl)(Cl)=O.[CH3:32][N:33]([CH:35]=O)[CH3:34]>>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:19]([S:20]([CH3:23])(=[O:21])=[O:22])[CH2:18][CH2:17][C:16]([C:24]([NH:19][C:13]4[CH:14]=[CH:27][C:10]([CH2:35][N:33]([CH3:32])[CH:34]5[CH2:5][CH2:4][O:3][CH2:1][CH2:2]5)=[CH:11][CH:12]=4)=[O:25])=[CH:15][C:14]=3[CH:27]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24386Thionyl ChlorideHCID 22329072HCID 22329072, compound

Product 1

HCID 22329109HCID 22329109, compound

Procedure

In DMF (12 ml) was suspended 7-(4-ethoxyphenyl)-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.13 g). To the suspension was added, under ice-cooling, thionyl chloride (0.04 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 (0.08 g) and triethylamine (0.14 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-ethoxyphenyl)-1-methanesulfonyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl]amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (0.16 g) as colorless crystals.

Workup

  1. additionTo the suspension was 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 (0.08 g) and triethylamine (0.14 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-2c18ceee11d140edb2b6f7fd6d97e40f
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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