Dimethylformamide → HCID 22328997, compound

HRID 586824Notes

Reaction equation

HRID 586824 reaction equation
[CH3:1][S:2]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:28]([OH:30])=O)[CH2:7][CH2:6]1)(=[O:4])=[O:3].S(Cl)(Cl)=O.[CH3:35][N:36]([CH:38]=O)[CH3:37]>>[CH3:1][S:2]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:20][CH:21]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:28]([NH:5][C:11]2[CH:12]=[CH:13][C:14]([CH2:38][N:36]([CH3:35])[CH:37]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:15][CH:10]=2)=[O:30])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22329077HCID 22329077, compound

Product 1

HCID 22328997HCID 22328997, compound

Procedure

In DMF (10 ml) was dissolved 1-methanesulfonyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.3 g). To the solution was added, under ice-cooling, thionyl chloride (0.15 ml), and the mixture was stirred at room temperature for 30 minutes. Under reduced pressure, the solvent was evaporated, and the residue was suspended in THF (50 ml). The suspension was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.19 g) and triethylamine (0.5 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/ethanol to give 1-methanesulfonyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide (0.26 g) as pale crystals.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. customUnder reduced pressure, the solvent was evaporated
  4. additionThe suspension was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.19 g) and triethylamine (0.5 ml) in THF (5 ml), under ice-
  5. temperaturecooling
  6. customUnder reduced pressure, the solvent was evaporated
  7. additionTo the residue was added water
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with water and saturated brine
  10. dry with materialdried with anhydrous magnesium sulfate
  11. customthe solvent was evaporated
  12. customto give crude crystals, which
  13. customwere recrystallized from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-e2ac0c8bb8e84f2780724f787e64c188
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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