Triethylamine → 4-[4-(pyrimidin-2-ylmethoxy)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid adamantan-2-ylamide

Participants

Reaction Steps

0.095 g of 1-[4-(pyrimidin-2-ylmethoxy)phenyl]-1,2,3,4-tetrahydroquinoxaline is placed in 3 ml of dichloromethane at 0° C. under nitrogen. 0.09 ml of triethylamine and 0.031 g of triphosgene are added. The mixture is stirred at ambient temperature for 2 h 30, 0.01 g of triphosgene is then added and stirring is maintained for 2 h. 0.12 ml of triethylamine and 0.062 g of adamantan-2-ylamine hydrochloride are then added. Stirring is maintained at ambient temperature for 1 h. After hydrolysis, the reaction medium is extracted with ethyl acetate until the aqueous phase has been completely extracted. The organic phases are combined, washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of methanol in dichloromethane varying from 0% to 9/1. 0.03 g of 4-[4-(pyrimidin-2-ylmethoxy)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid adamantan-2-ylamide is obtained, which is triturated from a mixture of ethyl acetate and diisopropyl ether.

Provenance & Evidence