Triethylamine → N-[2-(4-Chlorophenyl)-3-isopropyl-imidazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanamide

Participants

Reaction Steps

A mixture of 2-(4-chlorophenyl)-3-isopropyl-imidazol-4-amine (0.10 g, 0.43 mmol), 2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanoic acid (0.09 g, 0.43 mmol), HATU (0.16 g, 0.43 mmol), and Et3N (200 μL, 1.4 mmol) in CH2Cl2 (1 mL) was stirred at room temperature for 30 min. The reaction mixture was then diluted with 10 mL of saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic layer was subsequently washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude product was purified by flash chromatography (SiO2, 100% EtOAc-30% MeOH/EtOAc) to afford the titled compound as a white solid (0.046 g, 0.10 mmol, 23% yield). 1H NMR (400 MHz, CDCl3) 7.52 (s, 1H), 7.44 (d, J=8.0 Hz, 2H), 7.32 (d, J=8.0 Hz, 2H), 7.07 (s, 1H), 5.18 (q, J=7.1 Hz, 1H), 4.36 (q, J=7.0 Hz, 1H), 2.42 (s, 3H), 1.78 (d, J=7.1 Hz, 3H), 1.33 (d, J=7.0 Hz, 6H). MS: (ES) m/z calculated for C20H21ClF3N5O [M+H]+ 440.1, found 440.4.

Provenance & Evidence