Morpholine → HCID 89922660, compound

Participants

Reaction Steps

2-((2-chloro-5-cyano-4-(3-oxobutyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (38 mg, 0.070 mmol) and morpholine (9.2 mg, 0.10 mmol) was taken up in THF (0.2 mL) and MeOH (0.2 mL). Trimethyl orthoformate (0.078 mL, 0.070 mmol) and sodium cyanoborohydride (8.8 mg, 0.14 mmol) was then added. The reaction was stirred at room temperature overnight. The reaction was diluted with EtOAc and washed with aq. NaHCO3, then brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The material was taken up in DCM (0.25 mL) and anisole (0.025 mL) was added, followed by TFA (0.25 mL). The reaction was stirred at room temperature overnight. The reaction was then concentrated in vacuo and purified by preparative HPLC to provide 2-((2-chloro-5-cyano-4-(3-morpholinobutyl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (15.3 mg, 0.030 mmol, 42.5% yield).

Provenance & Evidence