1-Hydroxybenzotriazole → 4'-Bromo-2'-[(5-chloro-2-pyridyl)carbamoyl]-6'-hydroxy-1-isopropylpiperidine-4-carboxanilide hydrochloride

Participants

Reaction Steps

2-Amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (2.39 g) and 1.32 g of 1-isopropylpiperidine-4-carboxylic acid were dissolved in 35 ml of N,N-dimethylformamide, then 2.02 g of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride, 1.42 g of 1-hydroxybenzotriazole and 1.46 ml of triethylamine were added thereto and the mixture was stirred at room temperature for 22 hours. To the reaction solution were added 105 ml of water and 105 ml of ethyl acetate, the mixture was stirred at room temperature for 3 hours and the resulting precipitate was filtered, washed with ethyl acetate and water and dried in vacuo. The resulting solid was suspended in 60 ml of ethanol, 5 ml of 1N hydrochloric acid were added thereto and the mixture was stirred at room temperature for 30 hours. The resulting precipitate was filtered, washed with ethanol and dried in vacuo to give 1.35 g of 4′-bromo-2′-[(5-chloro-2-pyridyl)carbamoyl]-6′-hydroxy-1-isopropylpiperidine-4-carboxanilide hydrochloride.

Provenance & Evidence