Sodium hydride → HCID 11419939, compound

Participants

Reaction Conditions

Reaction Steps

1-[4-(2-Hydroxyethoxy)phenyl]-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide (100 mg, 0.26 mmol) and sodium hydride (6 mg, 0.26 mmol) were dissolved in anhydrous DMF (2 mL) under N2 atmosphere. The reaction mixture was heated to 60° C. until hydrogen gas evolution ceased. 2-Chloropyrazine (35 mg, 0.31 mmol, 28 μL) was then added drop-wise and the reaction was heated to 100° C. After 18 h, the reaction mixture was concentrated in vacuo and purified by mass-directed purification to provide 1-{4-[2-(Pyrazin-2-yloxy)ethoxy]phenyl}-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide (OSIP484814AA) as a white powder. 1H NMR (d6-DMSO, 400 MHz): δ 9.17 (brt, J=6.0 Hz, 1H), 8.60 (s, 1H), 8.58 (d, J=1.6 Hz, 1H), 8.47 (dd, J=5.2, 1.2 Hz, 1H), 8.40 (d, J=0.8 Hz, 1H), 8.37 (d, J=1.2 Hz, 1H), 8.26 (s, 2H), 7.90 (dd, J=8.6, 1.8 Hz, 1H), 7.76 (ddd, J=8.2, 1.8 Hz, 1H), 7.65-7.55 (m, 3H), 7.37 (ddd, J=8.0, 4.8, 0.8 Hz, 1H), 7.24 (ddd, J=9.2, 2.2, 2.2 Hz, 2H), 4.69 (m, 2H), 4.54 (d, J=4.4 Hz, 2H), 4.47 (m, 2H). MS(ES+): m/z 467 (100) [MH+].

Provenance & Evidence