Diisopropylethylamine → N-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanamide

Participants

Reaction Steps

To a solution of 1-(4-fluorophenyl)-5-isopropylpyrazol-4-amine (0.03 g, 0.14 mmol) in DMF (1.0 mL) was added 2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanoic acid (0.031 g, 0.14 mmol), followed by diisopropylethylamine (0.042 g, 0.32 mmol) and HATU (0.057 g, 0.15 mmol). After stirring at room temperature for 1 h, the reaction was diluted with water and the aqueous layer was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude product was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the title compound as a white solid (0.0145 g, 0.034 mmol, 25%). 1H NMR (400 MHz, CDCl3) δ 7.92 (d, J=0.6 Hz, 1H), 7.46 (q, J=1.2 Hz, 1H), 7.33-7.24 (m, 2H), 7.21-7.11 (m, 2H), 6.63 (s, 1H), 4.92 (q, J=7.3 Hz, 1H), 2.93 (m, 1H), 2.49 (s, 3H), 1.89 (d, J=7.3 Hz, 3H), 1.04 (dd, J=10.3, 7.2 Hz, 6H); MS: (ES) m/z calculated for C20H21F4N5O [M+H]+ 424.2, found 424.0.

Provenance & Evidence