Diisopropylethylamine → HCID 178474065, compound

Participants

Reaction Steps

HATU (0.092 g, 0.241 mmol) was added to a solution of 5-(acetylamino)-1H-benzimidazole-2-carboxylic acid (0.035 g, 0.161 mmol), 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.050 g, 0.161 mmol), and DIPEA (0.031 g, 0.241 mmol) in DMF (1 mL). After stirring at RT overnight, the reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with water, dried over sodium sulfate and concentrated. The crude product was purified by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to give the title compound (0.007 g, 8.5%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 10.03 (s, 1H), 9.48 (s, 1H), 8.11 (m, 1H), 7.74-7.90 (m, 1H), 7.43-7.67 (m, 4H), 7.35-7.44 (m, 1H), 7.26-7.34 (m, 1H), 4.55 (s, 2H), 2.05 (s, 3H). MS: m/z 512 (M+1).

Provenance & Evidence