Triethylamine → N-[1-(4-chlorophenyl)-5-isopropyltriazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanamide

Participants

Reaction Steps

A mixture of 1-(4-chlorophenyl)-5-isopropyltriazol-4-amine (from step f, 0.025 g, 0.11 mmol), 2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanoic acid (0.031 g, 0.13 mmol), HATU (0.057 g, 0.13 mmol), and 100 μL of Et3N in 1 mL of CH2Cl2 was stirred at room temperature. After 30 minutes, the reaction mixture was diluted with 10 mL of aqueous saturated sodium bicarbonate and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) provided the title compound as a colorless solid (0.0051 g, 0.011 mmol, 10%). 1H NMR (400 MHz, CDCl3) δ 9.14 (s, 1H), 7.65 (s, 1H), 7.54 (d, J=8.3 Hz, 2H), 7.34 (d, J=8.3 Hz, 2H), 5.26 (q, J=7.4 Hz, 1H), 3.0-2.98 (m, 1H), 2.62 (s, 3H), 1.86 (d, J=7.4 Hz, 3H), 1.14 (t, J=6.4 Hz, 6H). MS: (ES) m/z calculated for C19H20ClF3N6O [M+H]+ 441.1, found 441.2.

Provenance & Evidence