Imidazo(1,2-a)pyridine-3-carboxylic acid → HCID 71280572, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (25 mg, 0.154 mmol) and 5-(5-(2,2-difluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2,4-dimethylaniline (150) (41 mg, 0.154 mmol) in ethylacetate (1 mL) was added propylphosphonic anhydride solution 50 wt % in ethyl acetate (184 uL, 0.308 mmol). The reaction was heated at 65° C. overnight. The reaction was cooled to room temperature and diluted with a solution of saturated sodium bicarbonate. The organic was separated and washed with water/brine mixture and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography and then by a 20×250 mm ChiralPak AD-H column to give (R)—N-(5-(5-(2,2-difluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2,4-dimethylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F108). 1H NMR (400 MHz, d4-MeOD) δ 10.04 (s, 1H), 9.46-9.44 (m, 1H), 8.57 (s, 1H), 7.95 (s, 1H), 7.79-7.76 (m, 1H), 7.53-7.49 (m, 1H), 7.36 (s, 1H), 7.18-7.15 (m, 1H), 3.74 (m, 1H), 2.55 (s, 3H), 2.47-2.35 (m, 2H), 2.31 (s, 3H). MS m/z 409.14 (M+1)+.

Provenance & Evidence