Diisopropylethylamine → N-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-2-[5-methyl-3-(trifluoromethyl)-1,2,4-triazol-1-yl]propanamide

Participants

Reaction Steps

To a solution of 1-(4-fluorophenyl)-5-isopropylpyrazol-4-amine (0.050 g, 0.23 mmol) in DMF (1.0 mL) was added 2-[5-methyl-3-(trifluoromethyl)-1,2,4-triazol-1-yl]propanoic acid (0.051 g, 0.23 mmol), followed by diisopropylethylamine (0.059 g, 0.46 mmol) and HATU (0.105 g, 0.28 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 (0.03 g, 0.0706 mmol, 31%). 1H NMR (400 MHz, CDCl3) δ 8.24 (s, 1H), 8.04-7.99 (m, 1H), 7.35-7.25 (m, 2H), 7.22-7.11 (m, 2H), 5.13 (q, J=7.2 Hz, 1H), 3.05-2.93 (m, 1H), 2.62 (s, 3H), 1.93 (d, J=7.2 Hz, 3H), 1.27 (dd, J=7.2, 2.9 Hz, 3H), 1.10 (d, J=7.1 Hz, 3H); MS: (ES) m/z calculated for C19H20F4N6O [M+H]+ 425.2, found 425.0.

Provenance & Evidence