Trifluoroacetic acid → HCID 68227533, compound

Participants

Reaction Steps

To a stirred solution of {1-[4-(4-chloro-3-methyl-6-oxo-8-phenyl-3,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tea-butyl ester and {1-[4-(4-chloro-1-methyl-6-oxo-8-phenyl-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (43 mg, 0.08 mmol) in DCM (1.5 mL) was added TFA (0.5 mL) at RT. After 1 h, the reaction mixture was concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 20% MeOH in DCM) to yield a white solid. This crude residue was dissolved in a mixture of MeOH (0.5 mL), water (1.5 mL) and 1 M HCl (0.1 mL) and chromatographed on a 10 g C18 cartridge {30 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (4.0 mg). LCMS (Method E): RT=3.27 min, [M÷H]+=456/458. 1H NMR (300 MHz, CD3OD): δ 8.40 (s, 1H), 7.99 (s, 1H), 7.60-7.49 (m, 4H), 7.47-7.30 (m, 5H), 4.29 (s, 3H), 2.86-2.58 (m, 4H), 2.36-2.22 (m, 1H), 2.06-1.92 (m, 1H).

Provenance & Evidence