Sodium Hydroxide → HCID 67011554, compound

Participants

Reaction Steps

An aqueous solution of sodium hydroxide (0.107 mmol, 43 μL, 100 mg/mL) was added to methyl 5-(2-{4-[5-(pyridin-3-ylmethylaminocarbonyl)-1H-benzimidazol-1-yl]phenoxy}ethoxy)nicotinate (prepared according to the procedure described above utilising methyl 5-hydroxynicotinate in place of 3-hydroxypyridine, 37 mg, 0.07 mmol) in methanol and the mixture heated at reflux for 18 h. The mixture was then concentrated in vacuo and purified by preparative HPLC to yield the title compound. 1H NMR (d6-DMSO, 400 MHz): δ 9.15 (t, J=6.0 Hz, 1H), 8.64 (s, 1H), 8.60-8.50 (m, 2H), 8.40-8.39 (m, 2H), 8.38 (d, J=1.6 Hz, 1H), 8.35 (s, 1H), 7.87 (dd, J=8.4, 1.6 Hz, 1H), 7.78 (s, 1H), 7.73 (d, J=7.6 Hz, 1H), 7.59 (dd, J=12.4, 8.8 Hz, 3H), 7.35 (dd, J=7.6, 5.2 Hz, 1H), 7.23 (d, J=8.8 Hz, 2H), 4.51 (d, J=6.0 Hz, 2H), 4.50-4.4 (m, 4H); MS (ES+): m/z 510 [MH+], 511 [MH+2].

Provenance & Evidence