Benzaldehyde → N4-[4-tert-Butyl-2-(1-benzylpiperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

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Reaction Steps

In a 4 mL screw cap vial, N4-[4-tert-butyl-2-(piperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine (38 mg, 76 μmol) was dissolved in 1 mL of freshly prepared dry 95:5 MeOH:AcOH. Benzaldehyde (24.1 mg, 227 μmol, 3 eq) was added and the vial was capped. After 10 minutes, sodium cyanoborohydride solution (0.5 mL of a 19.0 mg/mL freshly prepared stock in dry 95:5 MeOH:AcOH, 9.51 mg NaCNBH3, 151 μmol, 2 eq) was then added to the solution. The vial was re-capped and shaken overnight at room temperature. The mixture was then purified using the method described in Example 34-B to provide the desired compound as a yellow solid (47.5 mg, 106%).

Provenance & Evidence