Trifluoroacetic acid → 2-((2-Chloro-5-cyano-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (42.6 mg, 0.120 mmol), 3-amino-4-chloro-5-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzonitrile, TFA (45 mg, 0.120 mmol), palladium acetate (8.09 mg, 0.036 mmol), DPPF (6.66 mg, 0.012 mmol), Xantphos (6.95 mg, 0.012 mmol), and cesium carbonate (117 mg, 0.360 mmol) were combined in a vial and dioxane (801 μl) was added. The vial was evacuated and backfilled with nitrogen (3×), then heated at 100° C. 4 h. The reaction mixture was diluted with ethyl acetate and vacuum filtered through a pad of Celite. The filtrate was concentrated in vacuo and the crude material purified by column chromatography on the ISCO system (12 g, 0-5% MeOH/CH2Cl2). 2-((2-Chloro-5-cyano-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (30 mg) was isolated as a pale yellow solid.

Provenance & Evidence