1,2-Dichloroethane → 2-(4-(6-(trifluoromethyl)-1H-indazol-4-yl)-1H-pyrazol-1-yl)acetamide

Participants

Reaction Steps

To 2-(4-(6-(trifluoromethyl)-1H-indazol-4-yl)-1H-pyrazol-1-yl)acetic acid (0.052 g, 0.168 mmol) in DMF (3 mL) were added HOBt (0.029 g, 0.218 mmol), EDC (0.045 g, 0.235 mmol), ammonium chloride (0.045 g, 0.838 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (0.146 mL, 0.838 mmol). The reaction mixture was stirred for 18 hours at room temperature. The crude mixture was subsequently purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column) eluting with a gradient of 20-30% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) to give the title compound as white solid (0.016 g, 31%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.84 (s, 2H), 7.33 (br s, 1 H), 7.51-7.68 (m, 2H), 7.75 (s, 1H), 8.23 (d, J=0.76 Hz, 1H), 8.56 (d, J=4.29 Hz, 2H), 13.62 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C13H10F3N5O, 310.1. found 310.

Provenance & Evidence