Water → 3-[(E)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one

Participants

Reaction Steps

In a microwave tube, to a solution of 3-benzoyl-4-methyl-1,2,4-oxadiazol-5(4H)-one (500 mg, 2.44 mmol, 1 eq.) in iPrOH (10 ml) were added 6-[(aminooxy)methyl]pyridin-2-amine (340 mg, 2.44 mmol, 1 eq.) followed by pTSA.H2O (578 mg, 2.93 mmol, 1.2 eq.). The reaction was microwaved at 160° C. for 2 h then was quenched by addition of water and extracted with EtOAc (3×50 ml). The organics were combined, washed with aq. sat. NaHCO3, dried over MgSO4 and concentrated. The residue was purified by preparative HPLC to give 3-[(Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one (200 mg, 25%) and 3-[(E)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one (62 mg, 8%).

Provenance & Evidence