HCID 71280491, compound → HCID 71280656, compound

Participants

Reaction Steps

To a stirring solution of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxamide (F53) (40 mg, 0.083 mmol) in anhydrous THF (2 mL) at −78° C. under a stream of Argon was added methylmagnesium bromide (83 uL, 0.25 mmol). The reaction was stirred to room temperature for 30 minutes. The reaction was cooled to 0° C. and was quenched with saturated NH4Cl (2 mL). The crude product was extracted with ethylacetate. The organic was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified by reverse phase preparative HPLC to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(3-hydroxy-3-methylbutyl)imidazo[1,2-a]pyridine-3-carboxamide (F54). 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s, 1H), 9.36 (s, 1H), 8.68 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.86-7.82 (m, 2H), 7.65-7.62 (m, 1H), 7.51 (d, J=8.4 Hz, 1H), 3.91-3.84 (m, 1H), 3.25-3.04 (m, 4H), 2.78-2.73 (m, 2H), 2.37 (s, 3H), 1.71-1.67 (m, 2H), 1.16 (s, 6H). MS m/z 496.21 (M+1)+.

Provenance & Evidence