Dimethylformamide → HCID 69522671, compound

Participants

Reaction Steps

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (438 mg) in tetrahydrofuran (10 ml) was added one droplet of DMF. Then, thionyl chloride (0.095 ml) was added to the mixture at 0° C., and the mixture was allowed to be at room temperature under nitrogen atmosphere and the mixture was stirred for 1 hour. This solution was added to a solution of 4-[(thiazol-2-ylmethyl)sulfanyl]aniline (265 mg) and triethylamine (3.6 ml) in tetrahydrofuran (10 ml) at 0° C. The mixture was stirred overnight at room temperature under nitrogen atmosphere, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) and was recrystallized from hexane-ethyl acetate, to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[(thiazol-2-ylmethyl)sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (424 mg) (Compound 316) as yellow crystals.

Provenance & Evidence