To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-trifluoroacetyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.5 g), 1-hydroxybenzotriazole (0.28 g), (4-aminophenyl)(5-methylpyridin-2-yl)methanol (0.29 g) and triethylamine (0.60 ml) in DMF (10 ml) were added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.40 g) and 4-dimethylaminopyridine (1 flake) at room temperature and the mixture was stirred for 3 days. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:1→2:1) and further recrystallized to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[hydroxy(5-methylpyridin-2-yl)methyl]phenyl]-1-trifluoroacetyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 103) (529.9 mg) as pale yellow crystals.
