Dimethylformamide → HCID 71280491, compound

Participants

Reaction Steps

To a stirring suspension of 6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxylic acid (78) (150 mg, 0.646 mmol) in anhydrous dichloromethane (5 mL) at 0° C. under Argon was added dropwise oxalyl chloride (60 μL, 0.710 mmol). Then, a drop of anhydrous N,N-dimethylformamide was added and the reaction mixture was stirred at room temperature for 45 minutes. The solvent was concentrated. A stirring mixture of the acid chloride and 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) (86 mg, 0.323 mmol) in anhydrous pyridine (3 mL) was stirred at room temperature for 3 hours. The crude product was purified by silica chromatography to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxamide (F53). 1H NMR (400 MHz, d6-DMSO) δ 10.19 (s, 1H), 9.37 (s, 1H), 8.70 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.86-7.83 (m, 2H), 7.66 (dd, J=1.6, 9.2 Hz, 1H), 7.51 (d, J=8.0 Hz, 1H), 3.92-3.84 (m, 1H), 3.24-3.05 (m, 4H), 2.89-2.86 (m, 4H), 2.37 (s, 3H), 2.11 (s, 3H). MS m/z 480.18 (M+1)+.

Provenance & Evidence