2-Aminoadamantane hydrochloride → N-(2-adamantyl)-1-(4-chloro-2-methyl-phenyl)-5-tert-butyl-pyrazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (Intermediate#115) (515 mg, 2.68 mmol) was added in one portion to 2-Adamantanamine hydrochloride (420 mg, 2.24 mmol), 5-tert-butyl-1-(4-chloro-2-methylphenyl)-1H-pyrazole-4-carboxylic acid (655 mg, 2.24 mmol), 1-Hydroxybenzotriazole (363 mg, 2.68 mmol) and N-Ethyldiisopropylamine (1.149 mL, 6.71 mmol) in DMF (10 mL). The resulting mixture was stirred at 20° C. for 18 hours. The reaction mixture was diluted with Et2O (100 mL), and washed sequentially with water (3×25 mL), and saturated brine (25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford desired product N-(2-adamantyl)-1-(4-chloro-2-methyl-phenyl)-5-tert-butyl-pyrazole-4-carboxamide (860 mg, 90%).

Provenance & Evidence