rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamate → rac-[1-({[7-(Cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic Acid tert-butyl Ester

Participants

Reaction Steps

A solution of 110 mg (0.364 mmol) of 7-(cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid from Example 120A in 1 ml of thionyl chloride was stirred at 100° C. for 1 h. After the reaction had ended, the solvent was drawn off under reduced pressure and the residue was suspended in 3 ml of dichloromethane and then added to a solution of 102.3 mg (0.473 mmol) of rac-(1-amino-2-methylpentan-2-yl)carbamic acid tert-butyl ester from Example 152A in 2 ml of dry dichloromethane. The resulting solution was stirred at room temperature overnight. The solvent was drawn off under reduced pressure and the residue was purified by flash chromatography using a prepacked silica gel cartridge (eluent:cyclohexane-ethyl acetate 10:1 to 1:1), which gave 40 mg (13% of theory, 59% pure) of the target compound.

Provenance & Evidence