p-(Trifluoromethoxy)phenyl isocyanate → 1-Propan-2-yl-1-[3-(1,3-thiazol-2-yl)benzyl]-3-[4-(trifluoromethoxy)phenyl]urea

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[3-(1,3-thiazol-2-yl)benzyl]propan-2-amine (35 mg, 0.15 mmol, 1.0 eq) in dichloromethane (2.5 mL) was added 1-isocyanato-4-(trifluoromethoxy)benzene (30 mg, 0.15 mmol, 1.0 eq) and the reaction was stirred at 23° C. for 16 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by reverse phase liquid chromatography (Gemini-NX C18, 5 μm, 30×100 mm column; 0-100% CH3CN/H2O gradient w/0.10% TFA present) to yield 1-propan-2-yl-1-[3-(1,3-thiazol-2-yl)benzyl]-3-[4-(trifluoromethoxy)phenyl]urea as a white solid. 1H NMR (500 MHz, DMSO): δ 8.58 (s, 1 H); 7.93-7.88 (m, 2 H); 7.80-7.75 (m, 2 H); 7.56 (d, J=8.7 Hz, 2 H); 7.45 (t, J=7.7 Hz, 1 H); 7.38 (d, J=7.7 Hz, 1 H); 7.22 (d, J=8.6 Hz, 2 H); 4.63 (s, 2 H); 4.54-4.48 (m, 1 H); 1.12 (d, J=6.6 Hz, 6 H). LRMS m/z (M+H) 436.1 found, 436.1 required.

Provenance & Evidence