Piperazine → HCID 178513577, compound

Participants

Reaction Steps

To a suspension of 2-{4-[(4-chloro-phenyl)-hydroxy-methyl]-phenyl}-1H-benzoimidazole-5-carboxylic acid amide (Example 20, 20.0 mg, 0.05 mmol) in CH2Cl2 (10 mL) was added thionyl chloride (0.04 mL, 0.06 mmol), and the mixture was stirred at RT for 1 h. Solvent was removed under reduced pressure, and the residue was dried under high vacuum. The crude product was dissolved in acetonitrile (10 mL). Piperazine (21 mg, 0.24 mmol) was added, and the mixture was heated to reflux for 12 h. Solvent was removed under reduced pressure, and purification of the residue by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2) afforded 17 mg (77%) of the title compound. HPLC (Method A): Rt=6.44. MS (ESI−): mass calculated for C25H24ClN5O, 445.2; m/z found, 444.6 [M−H]−. 1H NMR (500 MHz, CD3OD): δ 8.17 (br s, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.82–7.80 (dd, J=8.5, 1.5 Hz, 1H), 7.66 (d, J=8.4 Hz, 2H), 7.63 (br s, 1H), 7.50 (d, J=8.5 Hz, 2H), 7.35 (d, J=8.5 Hz, 2H), 4.56 (s, 1H), 3.31–3.27 (m, 8H).

Provenance & Evidence