Methanol → (R)-2-(3,4-Dichlorophenyl)-N-(2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

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Reaction Steps

To a solution of (R)-2-(5-amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate (100 mg, 0.0004 mol) in methylene chloride (2 mL, 0.03 mol) was added 3,4-dichlorophenyl acetic acid (120 mg, 0.00058 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (360 mg, 0.00096 mol) and N,N-diisopropylethylamine (300 μL, 0.002 mol). The reaction mixture was stirred overnight at room temperature. The mixture was then purified by column chromatography using an ethyl acetate:hexane (0-40%) gradient. The combined pure fractions were reduced in vacuo and taken up in methanol (3 mL, 0.07 mol), potassium carbonate (200 mg, 0.001 mol) and a few drops of water were added, and the mixture was stirred at room temperature for one hour. This was followed by purification using column chromatography (ethyl acetate:hexane, 0-100%) thus producing the title compound.

Provenance & Evidence