Water → HCID 71280509, compound

Participants

Reaction Steps

To a stirring suspension of 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylic acid (61) (260 mg, 0.74 mmol) in anhydrous dichloromethane (5 mL) at room temperature oxalyl chloride was added dropwise (0.19 mL, 2.22 mmol). Then, one drop of anhydrous DMF was added and the reaction mixture was stirred at room temperature for 15 minutes. The solvent was concentrated and the crude solid was added to a stirring solution of 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) (180 mg, 0.74 mmol) in anhydrous pyridine (5 mL) at room temperature. The reaction was stirred for 20 minutes and the solvent was removed to afford residue. To the above residue was added water (20 mL) and sonicated to give precipitate. Then the precipitate was filtered, dried in air and purified by silica chromatography to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxamide (64). MS m/z 596.3 (M+1)+.

Provenance & Evidence