Trifluoroacetic acid → HCID 89923044, compound

Participants

Reaction Steps

To a solution of 2-((2-chloro-5-cyano-3-((3-hydroxypropyl)amino)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (15 mg, 0.028 mmol) in dichloroethane (1 mL) was added Hunig's Base (0.048 mL, 0.276 mmol) followed by triphosgene (40.9 mg, 0.138 mmol). After stirring at room temperature for 1 h, LC-MS indicated the desired peak. After concentration, purification via flash chromatography (0-10% MeOH in DCM, 12 g) gave 15 mg of the PMB protected product. This was dissolved in 1 mL of dichloroethane and then 1 drop of anisole was added followed by 0.5 mL of TFA. The solution 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 (4.2 mg).

Provenance & Evidence