Compounds as cannabinoid receptor ligands
A technology of compounds and solvates, applied in the field of compounds as ligands of cannabinoid receptors, can solve problems such as no effective therapeutics or drugs yet
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Embodiment 1
[0442] 5-Chloro-2-methoxy-N-[(2Z)-3-[(2R)-tetrahydrofuran-2-ylmethyl]-5-[1-(trifluoromethyl)cyclopropyl]-1 ,3,4-Thiadiazole-2(3H)-ylidene]benzamide
Embodiment 1A
[0444] 5-[1-(trifluoromethyl)cyclopropyl]-1,3,4-thiadiazol-2-amine
[0445] A mixture of 1-(trifluoromethyl)cyclopropanecarboxylic acid (1 g, 6.5 mmol) and thiosemicarbazide (0.6 g, 6.5 mmol) / dioxane (8 ml) was heated to 90°C. Phosphorus oxychloride (0.6ml, 6.5mmol) was added to the hot reaction mixture. The reaction mixture was stirred at 90°C for 16 hours. The reaction mixture was then cooled, diluted with ethyl acetate (10ml) and washed with saturated NaHCO 3(10ml) quenched. The aqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organic extracts were washed with water (15 mL), dried (Na 2 SO 4 ), filtered and concentrated. The residue was triturated in hot hexanes to afford 0.5 g (37%) of the title compound. LC / MS (ESI + ) m / z 210 (M+H) + .
Embodiment 1B
[0447] (2R)-4-Tetrahydrofuran-2-ylmethylbenzenesulfonate
[0448] The title compound was prepared from commercially available (R)-(tetrahydrofuran-2-yl)methanol (Fluka) according to procedures as described in: Ebata, T.; Kawakami, H.; Koseki, K.; Matsushita, H. Agricultural and Biological Chemistry, 1991, 55(6), 1685-6. MS (ESI + ) m / z 257 (M+H) + .
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