4-Methylbenzaldehyde → HCID 178425443, compound

Participants

Reaction Steps

To a solution of 2-[4-(2-piperidin-2-yl-ethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide (0.10 g, 0.27 mmol) in DMF (1 mL) was added p-tolualdehyde (70 μL, 0.59 mmol), activated 4 Å molecular sieves, and NaB(OAc)3H (0.175 g, 0.82 mmol). The solution was stirred for 16 h and additional portions of aldehyde (1 equiv.) and NaB(OAc)3H (3 equiv.) were added. When HPLC monitoring indicated reaction completion, the solution was quenched with 1 N NaOH and purified by reverse phase HPLC (C18; H2O/CH3CN/0.01% TFA), providing 60 mg (48%) of product. HPLC (Method C): Rt=4.60. MS (ESI+): mass calcd. for C29H32N4O2, 468.25; m/z found, 469.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.18 (s, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.94 (d, J=8.6 Hz, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.34-7.32 (m, 2H), 7.23-7.20 (m, 2H), 7.15-7.13 (m, 2H), 4.33-4.10 (m, 3H), 3.45-3.39 (m, 1H), 3.15-3.07 (m, 1H), 2.90-2.85 (m, 1H), 2.72-2.67 (m, 1H), 2.42-2.37 (m, 1H), 2.20-2.10 (m, 1H), 1.93 (br s, 1H), 1.88-1.73 (m, 2H), 1.73-1.45(m, 3H).

Provenance & Evidence