Trifluoroacetic acid → N-(5-(5-(3-(3-hydroxypropylidene)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Steps

A stirring solution of N-(5-(5-(3-cyclopropyl-3-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F113) (130 mg, 0.303 mmol) in trifluoroacetic acid (1 mL) was stirred at room temperature for 1.5 hours. The solvent was concentrated and dried under high vacuum. The crude product was taken in MeOH (1 mL) and a saturated solution of sodium bicarbonate (0.2 mL). The reaction mixture was stirred for 15 minutes. The crude product was extracted with ethyl acetate. The organic phase was washed with water and dried over anhydrous sodium sulfate. The solvent was concentrated to obtain the desired product N-(5-(5-(3-(3-hydroxypropylidene)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F32). 1H NMR (400 MHz, d6-DMSO) δ 10.04 (s, 1H), 9.48-9.45 (m, 1H), 8.59 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.82 (dd, J=1.6 Hz, 7.6 Hz, 1H), 7.81-7.77 (m, 1H), 7.55-7.52 (m, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.20-7.16 (m, 1H), 5.28-5.23 (m, 1H), 4.50 (s, 1H), 3.98-3.89 (m, 1H), 3.40-3.37 (m, 2H), 3.23-3.14 (m, 2H), 3.09-3.03 (m, 2H), 2.36 (s, 3H), 2.08-2.02 (m, 2H). MS m/z 430.47 (M+1)+.

Provenance & Evidence