1,2-Dichloroethane → HCID 89783377, compound

Participants

Reaction Steps

A 20 mL vial was charged with 3-methoxy-4-(6-(trifluoromethyl)-1H-indazol-4-yl)benzoic acid (0.04 g, 0.119 mmol), EDC (0.034 g, 0.178 mmol), HOBt (0.027 g, 0.178 mmol), methanamine (0.178 mL, 0.357 mmol), DMA (1 mL), and DIPEA (0.062 mL, 0.357 mmol). The vial was capped and the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was subsequently diluted with methanol and purified via preparative HPLC, eluting with a gradient of 35-55% ACN (containing 0.1% formic acid) in H2O (containing 0.1% formic acid). The product fractions were collected and dried in vacuo to give a formic acid salt of the title compound as a white solid (23.6 mg, 56.8%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.84 (d, J=4.29 Hz, 3H), 3.83 (s, 3H), 7.37 (s, 1H), 7.49-7.56 (m, 1H), 7.56-7.62 (m, 1H), 7.65 (s, 1H), 7.94 (s, 1H), 7.97 (s, 1H), 8.60 (d, J=4.55 Hz, 1H), 13.61 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C17H14F3N3O2, 350.1. found 350.2.

Provenance & Evidence