Hydrochloric Acid → HCID 178494487, compound

Participants

Reaction Steps

To a solution of 2-[4-(hydroxy-phenyl-methyl)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide (Example 19, 8.7 mg, 0.02 mmol) in chloroform (1.0 mL) was added concentrated HCl (0.1 mL). The reaction mixture was stirred at RT for 2 h. Organics were removed under reduced pressure, and purification using preparative TLC (silica, 1% methanol saturated with ammonia/9% methanol/CH2Cl2) afforded 4.2 mg (47%) of the title compound. HPLC (Method A): Rt=6.97. MS (ESI+): mass calculated for C22H19N3O2, 357.1; m/z found, 358.2 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 8.18 (br s, 1H), 8.08 (d, J=8.2 Hz, 2H), 7.82 (br d, J=8.0 Hz, 1H), 7.64 (br s, 1H), 7.56 (d, J=8.3 Hz, 2H), 7.40 (d, J=8.0 Hz, 2H), 7.35 (t, J=7.5 Hz, 2H), 7.28–7.25 (m, 1H), 5.39 (s, 1H), 3.40 (s, 3H).

Provenance & Evidence