Dimethylformamide → HCID 24760964, compound

Participants

Reaction Conditions

Reaction Steps

Into a 20 ml reaction vial was combined N-(2-(5-amino-1-oxoisoquinolin-2(1H)-yl)ethyl)acetamide (20 mg, 0.00008 mol), 2-(4-chloro-3-fluorophenyl)acetic acid (30.55 mg, 0.0001620 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (72.66 mg, 0.0001911 mol) N,N-diisopropylethylamine (61.6 μL, 0.000353 mol), and N,N-dimethylformamide (1 mL, 0.02 mol). The mixture was heated at 50° C. for two hours, allowed to cool and poured onto sat sodium bicarbonate (200 ml). The mixture was extraced with methylene chloride (3×100 ml). The combined extracts were dried over sodium sulfate and reduced in vacuo. The mixture was purified by reverse phase prep HPLC using an acetonitrile:water gradient at pH 10. The combined pure fractions were reduced in vacuo to yield the compound as an off white solid.

Provenance & Evidence