Methanol → HCID 86671022, compound

Participants

Reaction Steps

A solution of 3-[4-(1-amino-cyclobutyl)-phenyl]-7-methoxy-2-phenyl-pyrano[2,3-b]pyridin-4-one hydrochloride (20 mg, 0.046 mmol) in 33% hydrogen bromide solution in AcOH (0.5 mL) was heated in a microwave oven at 100° C. for 30 minutes. The reaction mixture was added to a mixture of MeOH (10 mL) and water (5 mL) and the resultant solution passed through a 2 g SCX cartridge. The product was not retained by the cartridge. The washings containing the product were concentrated, the pH of the mixture was adjusted to ˜4 by addition of aqueous sodium hydroxide solution, and chromatographed on a 5 g C18 cartridge {gradient 20 to 70% MeOH in water+1M HCl (0.12 mL in each 10 mL of eluent)}. Fractions containing product were combined and concentrated in vacuo. The resulting residue was chromatographed on a 2 g C18 cartridge {gradient 20 to 60% MeOH in water+1M HCl (0.06 mL in each 5 mL of eluent)} to give the title compound (17.7 mg, 91%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.30 (d, J=9.2 Hz, 1H), 7.50-7.47 (m, 2H), 7.45-7.38 (m, 3H), 7.34-7.29 (m, 4H), 6.73 (d, J=9.0 Hz, 1H), 2.80-2.73 (m, 2H), 2.66-2.59 (m, 2H), 2.31-2.20 (m, 1H), 2.01-1.90 (m, 1H). LCMS (Method F): RT=6.97 min, [M−H]+=383.

Provenance & Evidence