1,1'-Carbonyldiimidazole → HCID 71288134, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 1-((tert-butoxycarbonyl)amino)-3,3-difluorocyclobutanecarboxylic acid (164) (45 mg, 0.18 mmol) in anhydrous NMP (1.3 mL) was added 1,1′-carbonyldiimidazole (CDI) (29 mg, 0.18 mmol). The reaction was stirred for 3 minutes. N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (69 mg, 0.22 mmol) was added and the reaction was stirred for 25 minutes. Then, the reaction was heated at 120° C. for 15 minutes. The crude product was taken up in ethyl acetate and water. The organic was washed with 2× water/brine mixture and dried over magnesium sulfate. The solvent was concentrated and the crude product was purified using silica gel chromatography using 60% ethyl acetate/hexanes to afford tert-butyl (3,3-difluoro-1-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)cyclobutyl)carbamate (165). MS m/z 525.2 (M+1)+

Provenance & Evidence