1-Hydroxybenzotriazole → N-[4-[N-(2-ethoxycarbonylethyl)-N-methylaminomethyl]phenyl]-7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide

Participants

Reaction Steps

To a solution of 7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (150 mg) and 1-hydroxybenzotriazole (101 mg) in DMF (5 ml) was added at room temperature 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (144 mg), and the mixture was stirred for 2 hours. To the mixture were added a solution of ethyl 3-[N-(4-aminobenzyl)-N-methylamino]propionate (133 mg) and triethylamine (0.1 ml) in DMF (5 ml) and a piece of 4-dimethylaminopyridine, and the mixture was stirred for 20 hours and concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with column chromatography (ethanol/ethyl acetate=1:9) and recrystallized from ethyl acetate/hexane to give yellow crystals of N-[4-[N-(2-ethoxycarbonylethyl)-N-methylaminomethyl]phenyl]-7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 24) (133.6 mg).

Provenance & Evidence