Methyl iodide → 3-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-4-methyl-1,2,4-oxadiazol-5-one

Participants

Reaction Steps

To a solution of 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-1,2,4-oxadiazol-5(4H)-one (2.89 g, 50% purity, 4.56 mmol, 1 eq.) in MeCN (50 ml) and DMF (10 ml) was added potassium carbonate (757 mg, 5.48 mmol, 1.2 eq.) followed by iodomethane (778 mg, 5.48 mmol, 1.2 eq.). The reaction was stirred at room temperature overnight. The reaction was quenched by addition of water and extracted with EtOAc (3×50 ml). The organics were combined, washed with aq. sat. NaCl, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one (930 mg, 61% yield) has a white solid.

Provenance & Evidence