Diisopropylethylamine → HCID 76902773, compound

Participants

Reaction Steps

To a solution of 5-ethyl-1-(4-fluorophenyl)pyrazol-4-amine (0.02 g, 0.1 mmol) in DMF (1.0 mL) was added 2-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetic acid (0.024 g, 0.10 mmol), followed by diisopropylethylamine (0.042 g, 0.32 mmol) and HATU (0.045 g, 0.12 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 (0.015 g, 0.035 mmol, 35%). 1H NMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.92 (s, 1H), 7.40-7.31 (m, 2H), 7.17 (dd, J=8.9, 8.1 Hz, 2H), 4.93 (s, 2H), 2.56 (q, J=7.6 Hz, 2H), 2.39 (s, 3H), 1.01 (t, J=7.6 Hz, 3H); MS: (ES) m/z calculated for C18H16ClF4N5O [M+H]+ 430.1, found 430.0.

Provenance & Evidence