Imidazole → HCID 54674967, compound

Participants

Reaction Conditions

Reaction Steps

A 4 mL vial was charged with (3aR,4R,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl 4-bromobenzenesulfonate (100 mg, 0.204 mmol) from Example 39 and 1H-imidazole (55.4 mg, 0.814 mmol) in toluene (0.5 mL). The reaction was heated at 90° C. for 24 hours, and then the reaction mixture was concentrated. The residue was purified by silica gel chromatography using 0-4% methanol (2 N ammonia)/dichloromethane as eluent to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 7.98 (s, 1H), 7.55 (d, J=8.1, 1H), 7.43 (s, 1H), 7.28 (t, J=1.2, 1H), 7.03 (d, J=7.3, 1H), 6.53 (d, J=8.6, 1H), 4.29 (dt, J=8.5, 6.6, 1H), 3.57-3.44 (m, 2H), 3.39 (dd, J=11.2, 7.2, 1H), 3.27 (dd, J=10.9, 4.2, 1H), 2.89-2.72 (m, 2H), 2.12 (dtd, J=11.3, 7.1, 3.8, 1H), 2.03-1.94 (m, 1H), 1.87 (ddd, J=17.3, 12.6, 8.6, 1H), 1.49-1.32 (m, 1H); MS (ESI+) m/z 323 (M+H)+.

Provenance & Evidence