Dimethylformamide → HCID 178450536, compound

Participants

Reaction Steps

In THF (8.1 ml) was dissolved 7-[4-(2-butoxyethoxy)phenyl]-1-(tetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.27 g). To the solution was added DMF (two droplets), followed by addition of thionyl chloride (51 μl) and stirring at room temperature for 1 hour, to give a solution, which was added dropwise to a solution of 4-[methyl(tetrahydropyranyl-4-yl)aminomethyl]aniline (145 mg) and triethylamine (1.62 ml) in THF (8.1 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was dissolved in ethanol. To the solution was added ethyl acetate, and the precipitates were collected by filtration, which was recrystallized from hexane/ethanol to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-1-(tetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 100) (42 mg).

Provenance & Evidence