Tetrahydrofuran → HCID 71280638, compound

Participants

Reaction Steps

To a stirring solution of methyl 3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)propanoate (93) (100 mg, 0.25 mmol) in anhydrous THF at −15° C. under argon was added dropwise a solution of ethylmagnesium bromide (247 L, 0.74 mmol). The reaction was stirred at room temperature for 16 hours. The reaction was quenched with saturated NH4Cl. The crude product was extracted with ethyl acetate, washed with water and brine and dried over sodium sulfate. The crude product was purified by preparative HPLC to yield both N-(5-(5-(2-(1-hydroxycyclopropyl)ethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F55a) and isopropyl 3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)propanoate (F55b). 1H NMR for (F55a) (400 MHz, CD2Cl2) δ 9.89 (d, J=6.8 Hz, 1H), 9.81 (s, 1H), 9.56 (s, 1H), 8.21 (s, 1H), 8.19 (d, J=8.0 Hz, 1H), 8.0 (t, J=8.0 Hz, 1H), 7.88 (dd, J=1.6, 7.6 Hz 1H), 7.53 (t, J=7.2 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 3.23 (t, J=7.2 Hz, 2H), 2.47 (s, 3H), 2.12 (t, J=7.2 Hz, 2H), 0.79 (t, J=6.8 Hz, 2H), 0.53 (t, J=6.8 Hz 2H). MS m/z 404.2 (M+1)+.

Provenance & Evidence