Acetic Acid → 2-((2-Chloro-5-cyano-3-(4-(3-hydroxyazetidin-1-yl)butan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Participants

Reaction Steps

2-((2-chloro-5-cyano-3-(4-oxobutan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (23 mg, 0.043 mmol) was taken up in THF (0.3 mL) and a solution of azetidin-3-ol (6.21 mg, 0.085 mmol) in MeOH (0.200 mL) was added. A drop of AcOH was added and the solution was stirred for 10 min. Next, sodium cyanoborohydride (5.34 mg, 0.085 mmol) was added and the reaction was stirred for 1 h. The reaction was diluted with EtOAc and washed with 2M K3PO4 solution. The organic layer was dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-10% MeOH/DCM; 12 g column). 2-((2-chloro-5-cyano-3-(4-(3-hydroxyazetidin-1-yl)butan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (13 mg) was obtained as a yellow glass.

Provenance & Evidence