Methylamine → 1-(4-(5-Amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)piperidin-1-yl)propan-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of 1-[4-[5-amino-6-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-1-piperidyl]propan-1-one and Na2CO3 (114 mg, 1.1 mmol) in tetrahydrofuran was treated with a solution of methylamine (1.3 mL of 2 M, 2.5 mmol) in THF and heated at 65° C. for 30 minutes. The reaction mixture was diluted with ethyl acetate, washed with 50% saturated sodium bicarbonate solution (2×20 mL), water, and brine. The solution was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via reverse phase HPLC (1-50% CH3CN/5 mM HCl) to provide 1-(4-(5-amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)piperidin-1-yl)propan-1-one.

Provenance & Evidence