Pyrazole → HCID 71280718, compound

Participants

Reaction Conditions

Reaction Steps

A stirring mixture of 3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)cyclobutyl methanesulfonate (81) (25 mg, 0.0535 mmol), 1H-pyrazole (7 mg, 0.0802 mmol) and cesium carbonate (26 mg, 0.107 mmol) in anhydrous DMF (1 mL) was heated at 60° C. for 1 hour. Then, the reaction was cooled to room temperature and filtered. The crude product was purified by reverse phase preparative HPLC to give N-(5-(5-(3-(1H-pyrazol-1-yl)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F45). 1H NMR (400 MHz, d6-DMSO) δ 10.20 (s, 1H), 9.54-9.51 (m, 1H), 8.71 (s, 1H), 8.10 (dd, J=1.6, 7.2 Hz, 1H), 7.89-7.85 (m, 3H), 7.70-7.66 (m, 1H), 7.54-7.50 (m, 2H), 7.33-7.29 (m, 1H), 6.28-6.25 (m, 1H), 5.04-4.96 (m, 1H), 3.82-3.73 (m, 1H), 3.10-2.85 (m, 4), 2.37 (s, 3H). MS m/z 440.18 (M+1)+.

Provenance & Evidence