Dimethyl Sulfoxide → (5-Fluoro-2-trifluoromethylphenyl)-{4-[5-(5-propyl-1H-imidazol-2-YL)pyridin-2-YL]piperazin-1-YL}methanone

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Reaction Steps

To a stirred solution of oxalyl chloride (0.029 g, 0.228 mmol) in CH2Cl2 (1.5 mL) was added dropwise DMSO (0.028 g, 0.358 mmol) at −78° C. under nitrogen. The resulting mixture was stirred for 10 minutes. To this mixture was added dropwise a solution of (5-fluoro-2-trifluoromethylphenyl)-{4-[5-(5-propyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl]piperazin-1-yl}methanone (0.052 g, 0.112 mmol) in dichloromethane (1.5 mL). The resulting mixture was stirred for 10 minutes followed by the addition of triethylamine (0.056 g, 0.553 mmol). The reaction mixture was stirred at −78° C. for 1 h, and then allowed to warm to ambient temperature and quenched with water. The aqueous phase was extracted with dichloromethane. The combined organic layers were dried over Na2SO4 and then concentrated. The crude product was purified by preparative TLC to afford the title compound in 10% yield (0.005 g). 1H NMR (300 MHz, CDCl3) δ 8.58 (s, 1H), 8.07 (dd, J=1.0, 9.0 Hz, 1H), 7.75 (dd, J=5.1, 8.8 Hz, 1H), 7.08 (dd, J=2.3, 7.9 Hz, 1H), 6.81 (s, 1H), 6.67 (d, J=9.0 Hz, 1H), 4.01-3.64 (m, 4H), 3.58-3.51 (m, 2H), 3.35-3.27 (m, 2H), 2.64-2.55 (m, 2H), 1.74-1.61 (m, 2H), 0.96 (t, J=7.3 Hz, 3H). MS (ES+) m/z 462 (M+1).

Provenance & Evidence