Dimethylformamide → HCID 22329102, compound

HRID 586886Notes

Reaction equation

HRID 586886 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[N:22]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:21][CH2:20][C:19]([C:27]([OH:29])=O)=[CH:18][C:17]=3[CH:30]=2)=[CH:9][CH:8]=1)[CH3:2].S(Cl)(Cl)=O.[CH3:35][N:36]([CH:38]=O)[CH3:37]>C1COCC1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[N:22]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:21][CH2:20][C:19]([C:27]([NH:22][C:16]4[CH:17]=[CH:30][C:13]([CH2:38][N:36]([CH3:35])[CH:37]5[CH2:5][CH2:4][O:3][CH2:1][CH2:2]5)=[CH:14][CH:15]=4)=[O:29])=[CH:18][C:17]=3[CH:30]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22328907HCID 22328907, compound

Product 1

HCID 22329102HCID 22329102, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (15 ml) was suspended 7-[4-(2-ethoxyethoxy)phenyl]-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.14 g). To the suspension were added, under ice-cooling, thionyl chloride (0.04 ml) and DMF (catalytic amount), and the mixture was stirred at room temperature for 1.5 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 (15 ml), under ice-cooling, and the mixture was stirred under nitrogen atmosphere at room temperature for 1 hour. 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 7-[4-(2-ethoxyethoxy)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 7) (0.15 g) as colorless amorphous.

Workup

  1. additionTo the suspension 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 (0.08 g) and triethylamine (0.14 ml) in THF (15 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

Sources & evidence

ORD record
ord-0f433cd772094e448136de8f22dc2afb
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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