Dimethylformamide → tert-Butyl 2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)ethyl(methyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A reaction vial was charged with tert-butyl 2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)ethyl(methyl)carbamate (150 mg, 0.00041 mol), 2-(3-fluoro-4-(trifluoromethyl)phenyl)acetic acid (200 mg, 0.0009 mol), N,N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (700 mg, 0.002 mol), N,N-diisopropylethylamine (0.3 mL, 0.002 mol), N,N-dimethylformamide (4 mL, 0.05 mol) and the reaction was stirred at 45° C. overnight. The reaction was then quenched with water, extracted with warm ethyl acetate, and the solvent removed under reduced pressure. The residue was purified by flash chromatography and then by reversed phase preparative HPLC to afford the product as an off white solid.

Provenance & Evidence