Acetic Acid → HCID 11233069, compound

Participants

Reaction Conditions

Reaction Steps

Activated manganese dioxide (600 mg) was added to a solution of the alcohol (12) (90 mg, 0.29 mmol) in a mixture of ethyl acetate (20 mL) and methanol (10 mL) and the mixture was stirred vigorously at 23° C. for 2 h. APCI-MS Found [M+H]=310. The reaction mixture was filtered through Celite, washing through with more ethyl acetate/methanol. The combined filtrates were concentrated to dryness to give the aldehyde, 1-Ethyl-3-(5-formyl-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea (13), which was used directly in the next step. To a solution of the crude aldehyde (13) in methanol (20 mL) was added NaCN (75 mg, 1.53 mmol) and acetic acid (26 μL, 0.46 mmol). Activated manganese dioxide (600 mg) was added last and the mixture was stirred at 23° C. for 3 h, then filtered through Celite, washing through with more methanol. The combined filtrates were concentrated to dryness to leave a solid which was adsorbed onto silica. Silica gel chromatography (ethyl acetate gradient to methanol/ethyl acetate (8:92)) provided 2-(3-Ethyl-ureido)-7-pyridin-3-yl-imidazo[1,2-a]pyridine-5-carboxylic acid methyl ester (14) (36 mg). HRFAB-MS Found: [M+H]=340.1413. C17H18N5O3 requires 340.1410.

Provenance & Evidence