1,1'-Carbonyldiimidazole → 3-[(Z)-N-[(6-amino-2-pyridinyl)methoxy]-C-phenylcarbonimidoyl]-4H-1,2,4-oxadiazol-5-one

Participants

Reaction Steps

To a solution of (1Z,2Z)-2-{[(6-aminopyridin-2-yl)methoxy]imino}-N′-hydroxy-2-phenylethanimidamide (3 g, 10.51 mmol, 1 eq.) in DMF (50 ml) was added CDI (1.70 g, 10.51 mmol, 1 eq.) and stirring at room temperature was allowed for 30 min before heated to 80° C. for 6 h. 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 triturated in MeCN and a white solid was isolated by filtration giving a first crop of 3-[(Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-1,2,4-oxadiazol-5(4H)-one (1.36 g, 36% yield). The mother liquor was concentrated and purified by chromatography on silica gel to give a second crop (2.9 g, 50% purity, 40% yield).

Provenance & Evidence