Diisopropylethylamine → HCID 178463700, compound

Participants

Reaction Steps

DMF (3 mL) and DIPEA (0.1 mL, 0.59 mmol) were added to a mixture of HATU (0.12 g, 0.32 mmol), 3-chloro-5-({6-chloro-3-[(ethylamino)methyl]-2-fluorophenyl}oxy)benzonitrile (0.10 g, 0.29 mmol) and 1H-imidazole-4-carboxylic acid (0.05 g, 0.41 mmol). The yellow solution was stirred at RT under a nitrogen atmosphere for 48 h then ethyl acetate (100 ml) and saturated NaHCO3 solution (100 ml) were added. The organic layer was washed with saturated NaHCO3 solution (2×100 ml), brine (150 mL), dried over MgSO4, filtered and concentrated. The crude material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA) to give the title compound (0.046 g, 36%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47-8.80 (m, 1H), 7.89-8.03 (m, 1H), 7.82 (s, 1H), 7.44-7.56 (m, 3H), 7.33 (t, 1H), 4.69-5.18 (m, 2H), 3.33-3.79 (m, 2H), 1.01-1.27 (m, 3H). LCMS m/z 431.2 (M−H).

Provenance & Evidence