Methanol → 3-[4-(1-Amino-cyclobutyl)-phenyl]-8-(3-fluoro-azetidin-1-ylmethyl)-2-phenyl-chromen-4-one

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Reaction Steps

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[8-(3-fluoro-azetidin-1-ylmethyl)-4-oxo-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was subjected to flash chromatography (SiO2, gradient 0 to 15% MeOH in DCM) to afford the title compound as a white solid (13 mg, 57%). 1H NMR (400 MHz, DMSO-d6): δ 7.97 (dd, J=8.0 and 1.7 Hz, 1H), 7.74 (dd, J=7.1 and 1.4 Hz, 1H), 7.47-7.28 (m, 8H), 7.08 (d, J=8.2 Hz, 2H), 5.27-5.06 (m, 1H), 3.94 (s, 2H), 3.65-3.56 (m, 2H), 3.29-3.16 (m, 2H), 2.36-2.27 (m, 2H), 2.11-1.87 (m, 5H), 1.65-1.54 (m, 1H). LCMS (Method E): RT=2.31 min, [M+H]+=455.

Provenance & Evidence