1,3,4-Thiadiazole, 2-amino-5-methyl- → 2-(2-Methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-methyl-[1,3,4]thiadiazol-2-ylamine (300 mg, 2.6 mmol), 4-bromo-3-oxo-butyric acid ethyl ester (908 mg, 2.6 mmol) and 5 mL of MeOH was combined in a sealed tube and was heated to 80° C. for 3 hours. The reaction was cooled and the MeOH was removed in vacuo. The residue was dissolved in dichloromethane and the organic solution was washed with saturated aqueous NaHCO3 solution (2×). The organic solution was dried over sodium sulfate, filtered and concentrated. The crude product was purified by Combiflash (Teledyne ISCO, Lincoln, Nebr.) chromatography using 0-100% EtOAc/heptanes. Both the desired product and (2-methyl-imidazo[2,1-b][1,3,4]thiadiazol-6-ylyacetic acid methyl ester (formed by trans esterification with solvent MeOH) were obtained with a total mass of 333 mg (54%). The crude mixture was used directly in the next step

Provenance & Evidence