Hydrochloric Acid → 7-[4-(1-Amino-cyclobutyl)-phenyl]-2-methyl-8-phenyl-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione hydrochloride

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Reaction Steps

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(2-methyl-3,6-dioxo-8-phenyl-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-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 (0.1 mL) and chromatographed on a 5 g C18 cartridge {30 to 70% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (13.5 mg, 77%). 1H NMR (400 MHz, DMSO-d6): δ 8.62 (br s, 3H), 7.86 (d, J=7.2 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.47-7.37 (m, 5H), 7.30 (d, J=8.3 Hz, 2H), 7.00 (d, J=7.2 Hz, 1H), 3.65 (s, 3H), 2.61-2.49 (m, 4H), 2.23-2.12 (m, 1H), 1.85-1.74 (m, 1H). LCMS (Method E): RT=2.95 min, [M+H]+=439.

Provenance & Evidence