3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-7-chloro-2-phenyl-pyrano[2,3-b]pyridin-4-one hydrochloride

Participants

Reaction Steps

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(7-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-b]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as the free base. The residue was dissolved in a mixture of MeOH (1 mL), water (4 mL) and 1 M HCl (0.15 mL) and chromatographed on a 2 g C18 cartridge {gradient 30 to 90% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)} to give the title compound (3.7 mg, 50%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.61 (d, J=8.3 Hz, 1H), 7.67 (d, J=8.0 Hz, 1H), 7.49-7.47 (m, 4H), 7.43-7.30 (m, 5H), 2.81-2.74 (m, 2H), 2.63-2.56 (m, 2H), 2.29-2.19 (m, 1H), 2.02-1.91 (m, 1H). LCMS (Method F): RT=8.90 min, [M+Na]+=418/420.

Provenance & Evidence