Methanol → HCID 86671027, compound

Participants

Reaction Steps

A solution of 3-[4-(1-amino-cyclobutyl)-phenyl]-8-methoxy-2-phenyl-pyrano[2,3-c]pyridin-4-one hydrochloride (22 mg, 0.051 mmol) in 33% hydrogen bromide solution in AcOH (0.5 mL) was heated in a microwave oven at 100° C. for 30 min. The reaction mixture was added to a mixture of MeOH (3 mL) and water (3 mL), the pH adjusted to ˜4 by addition of aqueous sodium hydroxide, and chromatographed on a 5 g C18 cartridge {gradient 35 to 70% MeOH in water+1 M HCl (0.12 mL in each 10 mL of eluent)}. Fractions containing product were concentrated in vacuo. The resultant residue was chromatographed on a 5 g C18 cartridge {gradient 35 to 70% MeOH in water+1 M HCl (0.06 mL in each 5 mL of eluent)} to give the title compound (15.1 mg, 71%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.33 (br s, 1H), 8.51 (br s, 3H), 7.48-7.33 (m, 8H), 7.28-7.26 (m, 2H), 6.61 (d, J=6.7 Hz, 1H), 2.60-2.49 (m, 4H), 2.23-2.12 (m, 1H), 1.85-1.74 (m, 1H). LCMS (Method F): RT=6.59 min, [M−H]−=383.

Provenance & Evidence