Ethyl chloroformate → ethyl 4-[4-[[methyl(1,2,3,4-tetrahydro-1-naphthalenyl)amino]carbonyl]-2-thiazolyl]-alpha-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-beta-oxo-1-piperidinepropanoate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1,2,3,4-tetrahydro-1-naphthalenyl)-4-thiazolecarboxamide (120 mg, 0.23 mmol) (i.e. the product of Example 2, Step E) in tetrahydrofuran (5 mL) at −78° C. was added a solution of lithium diisopropylamide in tetrahydrofuran (0.5 M, 2.0 mL, 1 mmol). After stirring at −78° C. for 30 minutes, a solution of ethyl chloroformate (100 μL) in tetrahydrofuran (2 mL) was added. The reaction mixture was stirred at −78° C. for 30 minutes more and then at 0° C. for 30 minutes. The reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated under reduced pressure, and the residue was purified by medium-pressure liquid chromatography using 75-100% of ethyl acetate in hexanes as eluant to provide 4 mg of the title product, a compound of the present invention.

Provenance & Evidence