2-((2-chloro-5-cyano-4-(3-oxopropyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (40 mg, 0.076 mmol) was taken up in THF (0.5 mL) and a solution of 3-methoxyazetidine (9.92 mg, 0.114 mmol) in MeOH (0.2 mL) was added, followed by a drop of AcOH and sodium cyanoborohydride (9.54 mg, 0.152 mmol). The reaction was stirred at room temperature for 1 h. The reaction was diluted with EtOAc and washed with water, then brine. The organic layer was 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-methoxyazetidin-1-yl)propyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (30 mg) was obtained as a colorless glass.
