Water → HCID 178513576, compound

Participants

Reaction Steps

To a solution of 2-{4-[(4-chloro-phenyl)-hydroxy-methyl]-phenyl}-1-H-benzoimidazole-5-carboxylic acid amide (Example 20, 50 mg, 0.13 mmol) in TFA (5.0 mL) was added sodium borohydride (211 mg, 4.2 equiv), and the reaction mixture was stirred at RT for 16 h. Water (5.0 mL) was added to the mixture, which was then adjusted to pH 9 with 1 N NaOH. The precipitate was collected by filtration and washed with H2O (20 mL). Purification by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2) afforded 39 mg (81%) of the title compound. HPLC (Method A): Rt=7.64. MS (ESI+): mass calculated for C21H16ClN3O, 361.1; m/z found, 362.2 [M+H]+. 1H NMR (500 MHz, CD3OD): δ 8.23 (d, J=1.4 Hz, 1H), 8.06 (d, J=8.2 Hz, 2H), 7.94-7.92 (dd, J=8.5, 1.6 Hz, 1H), 7-0.74 (d, J=8.5 Hz, 1H), 7.48 (d, J=8.2 Hz, 2H), 7.31 (d, J=8.4 Hz, 2H), 7.25 (d, J=8.4 Hz, 2H), 4.09 (s, 2H).

Provenance & Evidence