Ammonium Chloride → HCID 178505488, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,2,4-oxadiazole-5-carbonitrile (8 g, 21.79 mmol), sodium azide (2.125 g, 32.7 mmol) and ammonium chloride (5.83 g, 109 mmol) in DMF (43.6 ml) was heated at 100° C. for 0.5 h. The mixture was cooled to RT, diluted with 1N NaOH (50 mL), washed with Et2O (2×50 mL). The aqueous layer was acidified to pH about 1 with 2N HCl and extracted with EtOAc (3×75 mL). The combined organic fractions were washed with water (2×50 mL) then dried over Na2SO4. The solvent was evaporated under reduced pressure, the product dissolved in a small amount of EtOAc and precipitated with hexanes. The solid was filtered and washed with hexanes to afford the title compound. MS: m/z 410, 412 (MH+).

Provenance & Evidence