Hydrochloric Acid → HCID 131727492, compound

Participants

Reaction Steps

To a suspension of sodium 4-(4-(2-carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-2-(methylthio)pyrimidine-5-carboxylate (2.94 g, 6.72 mmol) in benzene (75 mL) was added thionyl chloride (4.9 mL, 62 mmol) and the solution was refluxed for 3 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was treated with benzene and again concentrated in vacuo to remove the residual thionyl chloride. The resulting solid was taken up in THF (75 mL) and was treated with 2,4-difluoroaniline (2.6 g, 20.2 mmol). After stirring overnight the mixture was acidified with dilute aqueous HCl, was diluted with water (400 mL), and filtered. The resulting solid was purified by repeated trituration with methanol or ethyl acetate to give the amide (1.69 g, 45%) as a solid. MS(ESI+) m/z 527 (M+H)+.

Provenance & Evidence