2,6-Lutidine → HCID 89923475, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl-4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-2-(dimethylcarbamoyl)piperazine-1-carboxylate (200 mg, 0.275 mmol) was taken up in DCM (2 mL) and cooled to 0° C. 2,6-Lutidine (0.096 mL, 0.826 mmol) was added, followed by drop wise addition of TMS-OTf (0.149 mL, 0.826 mmol). The reaction was stirred at 0° C. for 10 min, then brought to room temperature and stirred for 20 min. The reaction was quenched with 2M K3PO4 solution and extracted 2× with DCM. The organic layers were combined, dried over Na2SO4, filtered, and concentrated to give 188 mg of a yellow solid. The material was purified by flash column chromatography (0-70% 10% MeOH/DCM; 24 g column). 4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-N,N-dimethylpiperazine-2-carboxamide (133 mg) was obtained as a yellow solid.

Provenance & Evidence