4-Methoxybenzaldehyde → HCID 11490484, compound

Participants

Reaction Steps

A solution of 3-(2-aminoethyl)-N5,N5-bis(3-methylbutyl)-N2-(3,4,5-trimethoxyphenyl)-3H-imidazo[4,5-b]pyridine-2,5-diamine (83 mg, 1 eq) and p-anisaldehyde (25 mg, 1 eq) in dichloromethane (1.5 ml) is stirred for 6 hours at a temperature of approximately 20° C. The mixture is diluted with methanol (2 ml) then sodium triacetoxyborohydride (70 mg, 2 eq) is added. After stirring for 0.5 hour at a temperature of approximately 20° C., dichloromethane (20 ml) and water saturated with sodium hydrogen carbonate (10 ml) are added to the mixture. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 2:8) produces the expected compound (70 mg, 68% yield).

Provenance & Evidence