Dimethylformamide → N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-7-(4-propylphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide

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Reaction Steps

To a solution of 7-(4-propylphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (200 mg) in THF (5 ml) were added at room temperature thionyl chloride (0.09 ml) and a drop of DMF, and the mixture was stirred for 1 hour. The solvent was evaporated under reduced pressure, and the residue was dissolved in THF (12 ml). The solution was added dropwise at 0° C. to a solution of 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline[122 mg (0.55 mmol)] and triethylamine (0.14 ml) in THF (2 ml), and the mixture was stirred at room temperature for 4 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give pale yellow crystals, which were recrystallized from ethanol to give colorless crystals of N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-7-(4-propylphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 27) (195.0 mg).

Provenance & Evidence