Glutaric anhydride → 5-[[8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methoxy]-5-oxopentanoic Acid

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Reaction Steps

To a solution of 8-(2,6-dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine (0.3 g, 1.0 mmol) in tetrahydrofuran(10 ml) was added sodium hydride (50% in oil) (0.054 g, 1.1 mmol) and the mixture was stirred for 10 min. To the mixture was added glutaric anhydride (0.13 g, 1.1 mmol) and the reaction mixture was refluxed for 20 h. The solvent was evaporated under reduced pressure. The residue was partitioned between dichloromethane and water. The pH was adjusted to 4 with 2M HCl. The organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using dichloromethane:methanol (94:6) as eluent gave 0.034 g (8%) of the title compound.

Provenance & Evidence