1,1'-Carbonyldiimidazole → HCID 71280455, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3,3-difluorocyclobutanecarboxylic acid (264 mg, 1.94 mmol) in anhydrous NMP (6 mL) was added 1,1′-carbonyldiimidazole (315 mg, 1.94 mmol). The reaction was stirred for 5 minutes. 5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (500 mg, 1.62 mmol) was added and the reaction was stirred for 25 minutes, then heated in the microwave at 120° C. for 12 minutes. The crude product was purified by silica chromatography to give N-(5-(5-(3-fluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F13). 1H NMR (400 MHz, d6-DMSO) δ 10.19 (s, 1H), 9.53-9.50 (m, 1H), 8.70 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.90-7.87 (m, 1H), 7.83 (d, J=1.6, 8.0 Hz, 1H), 7.70-7.65 (m, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.33-7.29 (m, 1H), 3.93-3.84 (m, 1H), 3.25-3.02 (m, 4H), 2.37 (s, 3H). MS m/z 410.3 (M+1)+.

Provenance & Evidence