Dimethylformamide → HCID 69521974, compound

Participants

Reaction Steps

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.50 g) in THF (10 ml) were added thionyl chloride (0.12 ml) and DMF (1 droplet) at room temperature and the mixture was stirred for 2 hours. The reaction solution was concentrated under reduced pressure, a solution of the residue in THF (20 ml) was added dropwise at 0° C. to a solution of (S)-(+)-(4-aminophenyl)(2-pyridyl)methanol (0.24 g) and triethylamine (0.6 ml) in THF (5 ml), and the mixture was stirred for 18 hours at room temperature. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-diisopropylether to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[(S)-hydroxy(2-pyridyl)methyl]phenyl]-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 93) (542.7 mg) as colorless crystals.

Provenance & Evidence