Dimethylformamide → N3-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3,6-dicarboxamide

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of 6-carbamoylimidazo[1,2-a]pyridine-3-carboxylic acid (110) (50 mg, 0.172 mmol) in anhydrous dichloromethane (2 mL) at 0° C. under Argon was added dropwise oxalyl chloride (16 uL, 0.189 mmol). Then, a drop of anhydrous N,N-dimethylformamide was added and the reaction mixture was stirred at 0° C. for 1 hour. The solvent was concentrated. A stirring mixture of the acid chloride and methyl 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) (23 mg, 0.0861 mmol) in anhydrous pyridine (2 mL) was stirred at room temperature for 20 minutes. The crude product was purified by reverse phase preparative HPLC to give N3-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3,6-dicarboxamide (F62). 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s, 1H), 9.99-9.98 (m, 1H), 8.68 (s, 1H), 8.28 (s, 1H), 8.10 (d, J=1.6 Hz, 1H), 7.98 (dd, J=1.6, 9.2 Hz, 1H), 7.88-7.83 (m, 2H), 7.66 (s, 1H), 7.52 (d, J=8.0 Hz, 1H), 3.91-3.84 (m, 1H), 3.22-3.06 (m, 4H), 2.38 (s, 3H). MS m/z 452.14 (M+1)+.

Provenance & Evidence