Triethylamine → HCID 89923852, compound

Participants

Reaction Conditions

Reaction Steps

3-(5-chloro-2-cyano-4-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)propyl methanesulfonate (45 mg, 0.074 mmol) was taken up in acetonitrile (1 mL) and Et3N (0.015 mL, 0.111 mmol) and azetidin-3-ol (6.50 mg, 0.089 mmol) were added. The reaction was heated at 60° C. overnight. A mixture of product and SM detected by LCMS. An additional 1.2 eq of amine in 0.2 ml of DMF was added, and the reaction was heated at 60° C. overnight. The reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed 2× with water and once with brine, then dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-10% MeOH/DCM; 24 g column). 2-((2-chloro-5-cyano-4-(3-(3-hydroxyazetidin-1-yl)propyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (13 mg) was obtained as a purple glass.

Provenance & Evidence