Ethylene Glycol → N-(5-(5-(5,8-dioxaspiro[3,4]octan-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

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Ethylene glycol (10 mg), TsOH (5 mg) and N-(2-methyl-5-(5-(3-oxocyclobutyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (10) (50 mg) were combined in toluene (3 mL) and heated at 100° C. for 5 hours. The reaction was filtered and purified by preparative reverse phase HPLC to afford N-(5-(5-(5,8-dioxaspiro[3.4]octan-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F8). 1H NMR (400 MHz, d4-MeOH) δ 9.53 (d, J=7.2 Hz, 1H), 8.50 (s, 1H), 8.13-8.12 (m, 1H), 7.90 (dd, J=8.2, 2.0 Hz, 1H), 7.75 (d, J=9.6 Hz, 1H), 7.60-7.55 (m, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.18 (ddd, J=7.2, 7.2, 1.2 Hz, 1H), 4.45-4.43 (m, 1H), 3.98-3.81 (m, 4H), 3.32-3.31 (m, 4H), 2.43 (s, 3H). MS m/z 432.1 (M+1)+.

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