Diisopropylethylamine → N-[[4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]methyl]-4-methyl-thiadiazole-5-carboxamide

Participants

Reaction Steps

In a 1 dram vial, 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (25 mg, 0.080 mmol), DIPEA (0.014 mL, 0.080 mmol) and 4-methyl-1,2,3-thiadiazole-5-carboxylic acid (11.58 mg, 0.080 mmol) were dissolved in DMF (1 mL). HATU was added (30.6 mg, 0.080 mmol) and the solution stirred overnight. The reaction mixture was diluted to 2 mL with MeOH. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.014 g, 39%) as a white solid. 1H NMR (400 MHz, Acetone-d6): δ ppm 8.50 (br. s., 1H), 7.64 (t, 1H), 7.48-7.55 (m, 1H), 7.42-7.46 (m, 1H), 7.36-7.41 (m, 2H), 4.68 (d, 2H), 2.81-2.86 (m, 3H). LCMS m/z 436.8 (M+1).

Provenance & Evidence