Hydrochloric Acid → 3-(4-(Pyridin-2-ylamino)phenoxy)pyrazine-2-carboxylic acid

Participants

Reaction Steps

To a 250 mL round-bottomed flask containing methyl 3-(4-(pyridin-2-ylamino)phenoxy)pyrazine-2-carboxylate (7.44 g, 23.1 mmol) was added the mixed solvent of THF/MeOH/water. The tan solution was stirred at room temperature with addition of lithium hydroxide (1.66 g, 69.2 mmol). A white precipitate quickly formed. The suspension was acidified to pH 3 with 1 N HCl:diethyl ether, basified to pH 9 with 10 N NaOH, and reneutralized to pH 7 with concentrated HCl. The precipitate was collected by filtration and identified as the product. MS (ESI, pos. ion) m/z: 309.0 (M+1). IC50 (uM) 18.835.

Provenance & Evidence