Dimethylformamide → HCID 67011796, compound

Participants

Reaction Steps

1-[4-(2-Chloropropoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (prepared as described above using 1-(4-hydroxyphenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide as phenol and 1-bromo-3-chloropropane as alkylating agent) (100 mg, 0.24 mmol), 3-trifluoromethoxyphenol (42 mg, 31 μL 0.24 mmol) and potassium carbonate (36 mg, 0.26 mmol) were suspended in acetonitrile (2 mL), DMF (1 mL), and water (0.5 mL) and the mixture stirred at 60° C. for 18 h. The reaction mixture was then concentrated in vacuo and purified by reverse-phase preparative HPLC to give N-pyridin-3-ylmethyl-1-(4-{3-[3-(trifluoromethoxy) phenoxy]propoxy}phenyl)-1H-benzimidazole-5-carboxamide. 1H NMR (CDCl3, 400 MHz): δ 8.66 (d, J=2.0 Hz, 1H), 8.56 (dd, J=4.8, 1.2 Hz, 1H), 8.34 (d, J=1.6 Hz, 1H), 8.05 (s, 1H), 7.90 (dd, J=8.4, 1.6 Hz, 1H), 7.78 (ddd, J=8.0, 2.0, 2.0 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.43-7.37 (m, 2H), 7.34-7.28 (m, 2H), 7.20-7.08 (m, 3H), 6.90-6.78 (m, 3H), 4.75 (d, J=5.6 Hz, 2H), 4.27 (t, J=6.0 Hz, 2H), 4.22 (t, J=6.0 Hz, 2H), 2.35 (quin, J=6.0 Hz, 2H); MS (ES+): m/z 563 [MH+]

Provenance & Evidence