Novel compounds as cannabinoid receptor ligands

N-[(3E)-2-butyl-5-tert-butylisoxazol-3 (2H)-ylidene]-5-chloro-N′-cyano-2-methoxybenzenecarboximidamide

5-tert-butyl-2-butylisoxazol-3(2H)-imine

[0209]A mixture of 5-tert-butylisoxazol-3-amine (3.0 g, 21 mmol) and 1-bromobutane (3.5 mL, 32 mmol) was warmed to 85° C. and was allowed to stir for 70 h. The mixture was cooled to ambient temperature and was purified by column chromatography (silica gel, 60% hexanes / EtOAc) to give the title compound (4.2 g, 21 mmol, 99% yield). MS (DCI / NH3) m / z 197 (M+H)+.

Methyl N-5-tert-butyl-2-butylisoxazol-3(2H)-ylidene-N′-cyanocarbamimidothioate

[0210]To a solution of the product of Example 1A (2.0 g, 10 mmol) in acetonitrile (75 mL) was added triethylamine (1.4 mL, 10 mmol) followed by dimethyl cyanocarbonimidodithioate (1.4 g, 9.3 mmol). This mixture was warmed to 50° C. and was allowed to stir for 20 h. The mixture was cooled to ambient temperature, concentrated under reduced pressure and purified by column chromatography (silica gel, 60% hexanes / EtOAc) to provide the title compound (1.4 g, 4.7 mmol, 46% yield). MS (DCI / NH3) m / z 295 (M+H)+.