Diisopropylethylamine → HCID 178494103, compound

Participants

Reaction Steps

N,N-Diisopropylethylamine (4.6 mL, 26.4 mmol) and histamine.2HCl (1.16 g, 6.3 mmol) were successively added to a solution of acid 9a (2.3 g, 6 mmol) and HBTU (2.5 g, 6.6 mmol) in THF (70 mL) and DMF (35 mL). The reaction mixture was stirred at room temperature for 18 h and the solvent was evaporated in vacuo. Water (35 mL) was added to the residue and the fine precipitate was collected by filtration and suspended in methanol/water (1/1, 100 mL). The suspension was stirred at room temperature for 14 h and the solid was collected by filtration and dried in vacuo at 40° C. for 14 h to afford the desired 6-fluoro-N-[2-(1H-imidazol-4-yl)ethyl]-2-[2-hydroxy-5-(2-methoxypyridin-3-yl)phenyl] 1H-benzimidazole-5-carboxamide (10a) as a colorless solid. 1H NMR (DMSO-d6) δ 13.79-11.28 (br s, 2H), 8.45-8.16 (m, 3H), 7.94-7.91 (m, 2H), 7.69-7.51 (m, 3H), 7.17-7.11 (m, 2H), 6.88 (s, 1H), 3.92 (s, 3H), 3.59-3.48 (m, 2H), 2.79 (t, J=6.6 Hz, 2H). ES-MS MH+ 473.48. EA was in agreement with the formula C25H21FN6O3.0.75H2O.

Provenance & Evidence