21991-39-9

3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one is used as a reactant in the molecular design, synthesis and hypoglycemic activity of a series of thiazolidinediones in relation to improvement of insulin resistance and cardiac hypertrophy and bioavailability.

N2-methyl-2,3-pyridinediamine (66 mg, 0.54 mmol) and N,N'-carbonyldiimidazole (130.3 mg, 0.80 mmol, 1.5 eq.) were used as raw materials, and both of them were dissolved in tetrahydrofuran (THF) under the protection of argon, and the reaction was stirred at room temperature overnight. After completion of the reaction, the solvent was removed by vacuum evaporation, and the crude product obtained was recrystallized twice with water to finally obtain long fluffy pink crystals of 3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one in 70% yield.

[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 5, p. 1117 - 1123
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3052 - 3066
[3] Patent: US2011/319394, 2011, A1. Location in patent: Page/Page column 78-79