1,1'-Carbonyldiimidazole → HCID 71280455, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-fluorocyclobutanecarboxylic acid (76 mg, 0.647 mmol) in anhydrous NMP (1.5 mL) was added 1,1′-carbonyldiimidazole (105 mg, 0.647 mmol). The reaction was stirred for 5 minutes. 5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (100 mg, 0.323 mmol) was added and the reaction was stirred for 25 minutes, then heated in the microwave at 120° C. for 10 minutes. The crude product was purified by reverse phase preparative HPLC to give N-(5-(5-(3-fluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F36). 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s, 1H), 9.53-9.50 (m, 1H), 8.69 (s, 1H), 8.07 (d, J=1.6 Hz, 1H), 7.89-7.86 (m, 1H), 7.84 (dd, J=1.6, 8.0 Hz, 1H), 7.70-7.65 (m, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.32-7.29 (m, 1H), 5.48-5.28 (m, 1H), 3.99-3.91 (m, 1H), 2.81-2.73 (m, 4H), 2.37 (s, 3H). MS m/z 392.14 (M+1)+.

Provenance & Evidence