Example 14
To a solution of trans-1-(−4-(4-hydroxy-phenoxy)cyclohexyl)-3-(4-(trifluoromethoxy)phenyl)urea (104 mg, 0.25 mmol) in DCM (5 mL) was added acetyl chloride (71 mg, 0.90 mmol) and pyridine (23 mg, 0.29 mmol). After 30 minutes, additional pyridine (60 mg) and acetyl chloride (40 mg) were added. After an hour, the reaction mixture was diluted with EtOAc, extracted 3 times with K2CO3 (1M), dried over MgSO4 and evaporated. The resulting mixture was purified by flash chromatography over a gradient of 1:1 Hexanes:EtOAc to 100% EtOAc. The product was recrystallized in Hex:EtOAc to give a light brown solid (21 mg, 0.05 mmol, 20% yield). MP=204.1-209.0° C. (206.2° C.) 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s, 1H), 7.47 (d, J=9.0 Hz, 2H), 7.21 (d, J=8.7 Hz, 2H), 6.98 (q, J=9.0 Hz, 4H), 6.19 (d, J=7.6 Hz, 1H), 4.34-4.26 (b, 1H), 3.56-3.48 (b, 1H), 2.23 (s, 3H), 2.03 (d, J=12.3 Hz, 2H), 1.92 (d, J=12.7 Hz, 2H), 1.46 (q, J=11.6 Hz, 2H), 1.34 (q/=11.7 Hz, 2H).
