Sodium hydride → 1-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-(3,3,3-trifluoropropyl)imidazolidin-4-one

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Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one (200 mg, 0.38 mmol, 1.00 equiv), N,N-dimethylformamide (5 mL). This was followed by the addition of sodium hydride (46 mg, 1.15 mmol, 3.00 equiv, 60%), in portions at 0° C. The resulting solution was stirred for 30 min at 0° C. To this was added 1,1,1-trifluoro-3-iodopropane (863 mg, 3.85 mmol, 10.00 equiv). The resulting solution was allowed to react, with stirring, for an additional 4 days at 30° C. The reaction was then quenched by the addition of 10 ml of water. The resulting solution was extracted with 3×10 ml of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×20 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a TLC plate with EA/PE (5:1). This resulted in 10.9 mg (4%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-(3,3,3-trifluoropropyl)imidazolidin-4-one as a light yellow semi solid. (ES, m/z): [M+H]+ 616; 1H NMR (300 MHz, CDCl3) δ: 7.97 (s, 1H), 7.88 (d, J=6.0 Hz, 2H), 7.69-7.71 (m, 2H), 7.43 (d, J=7.8 Hz, 1H), 5.12 (s, 1H), 4.69 (s, 1H), 4.05-4.39 (m, 3H), 3.87 (s, 1H), 3.70 (t, J=7.2 Hz, 1H), 3.56 (t, J=7.2 Hz, 1H), 2.46-2.65 (m, 3H), 2.39 (s, 3H).

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