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

Participants

Reaction Steps

2-Amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (5.14 g) and 2.83 g of 1-isopropylpiperidine-4-carboxylic acid were dissolved in 75 ml of N,N-dimethylformamide, then 4.33 g of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride and 3.04 g of 1-hydroxybenzotriazole were added thereto and the mixture was stirred at room temperature for 46 hours. The reaction solution was added to 750 ml of 1% aqueous solution of sodium bicarbonate and 200 ml of ethyl acetate were added thereto. Ethyl acetate was evaporated therefrom in vacuo and the resulting solid was collected by filtration and washed with water. The resulting solid was suspended in 100 ml of methanol and 10 ml of water and the suspension was stirred for one night. The resulting precipitate was collected by filtration and dried in vacuo to give 4.41 g of 4′-bromo-2′-[(5-chloro-2-pyridyl)carbamoyl]-6′-hydroxy-1-isopropylpiperidine-4-carboxanilide.

Provenance & Evidence