Potassium Carbonate → HCID 86598044, compound

Participants

Reaction Steps

To a solution of 8-(trifluoromethyl)isoquinolin-5-amine (Description 93; 150 mg, 0.708 mmol) in CDCl3 (10 ml) was added [4-(trifiuoromethyl)benzyl]isocyanate (Description 58) [0.506M soln in DCM; 1.403 ml, 0.71 mmol) and the resulting mixture heated at reflux overnight. NMR analysis showed a deficit of the [4-(trifluoromethyl)benzyl]isocyanate in comparison to remaining 8-(trifluoromethyl)isoquinolin-5-amine so a further portion of [4-(trifluoromethyl)benzyl]isocyanate [0.506M solution in DCM] (1.403 ml; 0.71 mmol) was added and refluxing continued for 2 days. The cooled reaction mixture was evaporated to dryness and purified by column chromatography on silica elution with 1% MeOH in DCM+0.5% NH4OH. NMR showed the product was the bis acylated urea. This material was dissolved in methanol (5 ml) and K2CO3 (500 mg, 3.6 mmol) added and the mixture stirred at room temperature for 2.5 hours. The mixture was filtered and the residue purified by preparative TLC eluting with 10% MeOH in DCM+0.5% NH4OH to give the title compound (100 mg, 34%) as a white solid. m/z (ES+) 414 (M+H)+.

Provenance & Evidence