Hydrochloric Acid → HCID 67067825, compound

Participants

Reaction Steps

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(1-isopropyl-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 (3 mL), water (7 mL) and 1 M HCl (0.2 mL) and chromatographed on a 5 g C18 cartridge {gradient 30 to 70% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound (26.5 mg, 81%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.55 (br s, 3H), 8.33 (s, 1H), 7.82 (d, J=8.5 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.53-7.39 (m, 7H), 7.32 (d, J=8.2 Hz, 2H), 5.46 (septet, J=6.6 Hz, 1H), 2.62-2.49 (m, 4H), 2.23-2.13 (m, 1H), 1.86-1.74 (m, 1H), 1.59 (d, J=6.6 Hz, 6H). LCMS (Method E): RT=3.81 min, [M+H]+=450.

Provenance & Evidence