Cesium carbonate → 2-((2-Chloro-5-cyano-3-(4-(2-hydroxyethyl)-2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Participants

Reaction Steps

To a solution of 2-((2-chloro-5-cyano-3-(2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (10 mg, 0.018 mmol) in DMF (0.5 mL) was added cesium carbonate (25 mg, 0.077 mmol) followed by (2-bromoethoxy)(tert-butyl)dimethylsilane (8 mg, 0.033 mmol). The reaction mixture was stirred at room temperature overnight. LC-MS indicated desired product. It was then filtered through a pad of Celite, rinsed with EtOAc. The crude was dissolved in DCE (1 mL), anisole (7.68 μl, 0.070 mmol) (one drop) was added followed by TFA (0.5 mL, 6.49 mmol). The resulting reaction mixture was heated at 60° C. for 1 h. LC-MS indicated completion, and then it was cooled and concentrated. The crude was dissolved in methanol and neutralized with 7N ammonia in methanol. After stirring for 10 min it was concentrated, purification via preparative HPLC gave the title compound as a yellow solid (3.4 mg).

Provenance & Evidence