Trifluoroacetic acid → HCID 57920202, compound

Participants

Reaction Steps

Crude 3-(4-(benzyloxy)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate from example 24, step F (85% pure, approximately 80 mg) was taken up in methanol (2 mL), and a catalytic amount of Pearlman's catalyst was added. The system was hydrogenated at 60 psi for 24 hours, after which a small amount of product was observed. Trifluoroacetic acid (0.1 mL) was added, and the hydrogenation was continued at 60 psi H2 for 3 days, after which the reaction was approximately one third of the way completed. The reaction was filtered, and the product was isolated by prep HPLC (30×100 mm C18 column, 10-100% acetonitrile:water (10 mM ammonium acetate), 15 min, 45 mL/min) to afford the title compound (9.6 mg) as a white solid.

Provenance & Evidence