Dichloromethane → (R)-2-(6-Chloro-1-oxo-5-(2-adamantylacetamido)isoquinolin-2(1H)-yl)propanamide

Participants

Reaction Steps

To a solution of 1-adamantaneacetic acid (600 mg, 0.003 mol) in methylene chloride (5 mL, 0.08 mol) was added oxalyl chloride (0.3 mL, 0.003 mol) and a drop of N,N-dimethylformamide at 0° C. The reaction was stirred at that temperature for 1 h. the solvent was removed under reduced pressureunder reduced pressure and dried under nitrogen. The residue was redissolved in methylene chloride (5 mL, 0.08 mol) and added to a solution of (R)-2-(5-amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propanamide (420 mg, 0.0016 mol) in methylene chloride (5 mL, 0.08 mol) and N,N-dimethylformamide (2 mL, 0.02 mol), and stirred for 2 hours. the solvent was removed under reduced pressure and the residue was dissolved in 1:3 isopropyl alcohol/chloroform and washed with 1N hydrochloric acid. the solvent was removed under reduced pressure and the residue was purified by flash chromatography to afford the product as an off white solid.

Provenance & Evidence