Trifluoroacetic acid → 7-[4-(1-Amino-cyclobutyl)-phenyl]-3-chloro-1-methyl-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-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-(3-chloro-1-methyl-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was dissolved in a mixture of MeOH (1.5 mL), water (3.5 mL) and 1 M HCl (0.15 mL) and chromatographed on a 2 g C18 cartridge {gradient 30 to 65% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)} to give the title compound (10 mg, 36%, 2 steps) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.38 (br s, 3H), 7.82 (d, J=8.6 Hz, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.56-7.53 (m, 2H), 7.51-7.44 (m, 3H), 7.41-7.37 (m, 2H), 7.31 (d, J=8.2 Hz, 2H), 4.38 (s, 3H), 2.62-2.49 (m, 4H), 2.22-2.12 (m, 1H), 1.86-1.75 (m, 1H). LCMS (Method E): RT=3.51 min, [M+H]+=456/458.

Provenance & Evidence