Nitrogen → HCID 178436325, compound

Participants

Reaction Steps

A flask containing a solution of 2-{4-[1-(4-chloro-phenyl)-vinyl]-phenyl}-1H-benzoimidazole-5-carboxylic acid amide (Example 41, 30 mg, 0.08 mmol) in 1:1 ethanol/ethyl acetate (6.0 mL) was charged with N2 and evacuated (3×). Palladium on carbon (10 wt %) was added to the solution, and the flask was charged with H2 and evacuated (3×), and then maintained at ˜1 atm H2 for 2.5 h. The flask was evacuated and then charged with N2. The reaction mixture was filtered through a pad of Celite®, which was washed with ethanol (50 mL), ethyl acetate (50 mL) and then methanol (2×50 mL). The filtrate was concentrated under reduced pressure. Purification of the residue by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2) afforded the title compound (21 mg, 68%). TLC (silica, 1% methanol, saturated with ammonia/9% methanol/CH2Cl2): Rf=0.35. MS (ESI+): mass calculated for C22H18ClN3O, 375.1, m/z found, 376.1 [M+H]+. 1H NMR (500 MHz, CD3OD): δ 8.16 (br s, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.81 (d, J=8.3 Hz, 1H), 7.62 (br s, 1H), 7.43 (d, J=8.3 Hz, 2H), 7.30–7.26 (m, 4H), 4.27–4.24 (m, 1H), 1.67 (d, J=7.2 Hz, 3H).

Provenance & Evidence