Pyridine → HCID 69521911, compound

Participants

Reaction Steps

In THF (12 ml) was dissolved 7-[4-(2-butoxyethoxy)phenyl]-N-[4-(hydroxymethyl)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide (0.60 g), and pyridine (3 droplets) and thionyl chloride (0.16 ml) were added to the mixture. The solution was stirred at room temperature for 1 hour, and added dropwise to a solution of 1-methyl-1,2,3,4-tetrazole-5-thiol (154 mg) and triethylamine (1.23 ml) in THF (12 ml) at 0° C. The mixture was stirred at room temperature for 2 hours, and stirred for 16 hours at 50° C. After allowing to be cooled to room temperature, the reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 245) (520 mg).

Provenance & Evidence