Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

To a solution of tert-butyl 1-(4-(4-oxo-2-phenyl-8-vinyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate (15 mg, 0.030 mmol) in DCM was added 4 M HCl in 1,4-dioxane (0.05 mL, 2 mmol). The reaction mixture was stirred at RT for 4 h. The solvents were removed in vacuo. The product was chromatographed on a 5 g C18 cartridge {gradient 10 to 50% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as an HCl salt (5 mg, 38%). 1H NMR (500 MHz, CD3OD): δ 8.61 (d, 1H), 7.95 (d, 1H), 7.51-7.30 (m, 9H), 4.15-4.08 (m, 2H), 3.68-3.60 (m, 2H), 2.75-2.67 (m, 2H), 2.55-2.42 (m, 2H), 2.28-2.12 (m, 1H), 1.98-1.88 (m, 1H). LCMS (Method I): RT=4.49 min, [M+2]+=432.

Provenance & Evidence