Trifluoroacetic acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one

Participants

Reaction Steps

To a solution of {1-[4-(6-fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (22 mg, 0.045 mmol) in DCM (4 mL) was added TFA (1 mL). The mixture was stirred at RT for 1 h and then directly loaded onto an SCX cartridge (2 g, pre-wet using DCM). Impurities were removed by eluting with MeOH:DCM (1:1) and product eluted using NH3 solution (2M in MeOH):DCM (1:1) to give the title compound (14 mg, 82%). LCMS (Method F): RT=9.03 min, [M+H]+=386. 1H NMR (400 MHz, CDCl3): δ 7.92 (dd, J=8.3 and 3.2 Hz, 1H), 7.55 (dd, J=9.5 and 4.7 Hz, 1H), 7.47-7.32 (m, 6H), 7.29 (d, J=7.9 Hz, 2H), 7.19 (d, J=8.3 Hz, 2H), 2.61-2.50 (m, 2H), 2.22-2.00 (m, 3H), 1.82-1.69 (m, 1H).

Provenance & Evidence