Benzimidazole → 2-(1H-Benzimidazol-1-yl)-4-({[2-(trifluoromethyl)phenyl]methyl}-oxy)-1,3-thiazole-5-carboxamide

Participants

Reaction Steps

A solution of 2-chloro-4-({[2-(trifluoromethyl)phenyl]methyl}oxy)-1,3-thiazole-5-carboxamide (0.050 g, 0.14 mmol) and benzimidazole (0.010 g, 0.08 mmol) in DMF (4 mL) was heated at 75° C. in the presence of K2CO3 (0.011 g, 0.08 mmol) for 12 h. After the reaction mixture had cooled to rt, it was diluted with EtOAc (10 mL), washed with H2O (4×10 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 7.96 (d, J=7.7 Hz, 1H), 7.88 (d, J=7.7 Hz, 1H), 7.77 (d, J=7.7 Hz, 1H), 7.67-7.59 (m, 2H), 7.54-7.40 (m, 3H), 6.80 (bs, 1H), 5.82 (s, 2H), 5.63 (bs, 1H). MS m/z 419 (m+1).

Provenance & Evidence