Cesium carbonate → 2-((2-chloro-5-cyano-3-(1,1-dioxidotetrahydro-2H-isothiazolo[2,3-a]pyrazin-5 (3H)-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (40.2 mg, 0.113 mmol), 3-amino-4-chloro-5-(1,1-dioxidotetrahydro-2H-isothiazolo[2,3-a]pyrazin-5(3H)-yl)benzonitrile (37 mg, 0.113 mmol), palladium(II) acetate (6.74 mg, 0.030 mmol), XANTPHOS (6.55 mg, 0.011 mmol), DPPF (6.28 mg, 0.011 mmol) and cesium carbonate (96 mg, 0.294 mmol) in Dioxane (2 ml) was evacuated and back filled with nitrogen three time and was heated at 80° C. for 3 h. The reaction mixture was filtered through a celite pad and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (24 g column, eluting with 0-5% Methanol/DCM). 2-((2-chloro-5-cyano-3-(1,1-dioxidotetrahydro-2H-isothiazolo[2,3-a]pyrazin-5(3H)-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (21 mg) was obtained as a light brown solid

Provenance & Evidence