Acetyl chloride → 2-((3-(4-(1-Acetylazetidin-3-yl)piperazin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Participants

Reaction Steps

To a solution of 2-((3-(4-(azetidin-3-yl)piperazin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (100 mg, 0.164 mmol) in DCM (1.0 mL) was added TEA (0.069 mL, 0.492 mmol) followed by acetyl chloride (0.014 mL, 0.197 mmol) in a drop wise manner. The reaction mixture was allowed to warm to room temperature and stirred for overnight. The reaction mixture was diluted with dichloromethane (50 mL) and poured into a separating funnel containing saturated aqueous sodium bicarbonate (10 mL). The aqueous layer was extracted with dichloromethane (2×50 mL). The combined organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude material was precipitated from DCM/Hexane (Dissolved in minimum amount of DCM, precipitated by adding Hexane), filtered and dried to get the 2-((3-(4-(1-acetylazetidin-3-yl)piperazin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (110 mg) as a off white solid.

Provenance & Evidence