Triethylamine → HCID 67460233, compound

To a slurry of 5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid (0.23 g, 1.1 mmol) in dichloromethane (5 mL) was added oxalyl chloride (0.20 mL, 14 mmol) and one drop of N,N-dimethylformamide. After 45 minutes the reaction mixture was concentrated in vacuo and the resulting residue was dissolved in dichloromethane (10 mL). The reaction mixture was then added to a solution of ethyl 4-piperidinyl-2H-1,2,3-triazole-4-carboxylate (0.23 g) and triethylamine (0.20 mL, 1.4 mmol) in dichloromethane (10 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The organic layer was washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and the solvent was removed with a rotary evaporator. The residue was purified by medium pressure liquid chromatography (MPLC) using 35 to 60% ethyl acetate in hexanes as eluant to afford 0.35 g of the title compound as a white solid.

1. concentrationAfter 45 minutes the reaction mixture was concentrated in vacuo
2. dissolutionthe resulting residue was dissolved in dichloromethane (10 mL)
3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
4. dry with materialdried (Na2SO4)
5. customthe solvent was removed with a rotary evaporator
6. customThe residue was purified by medium pressure liquid chromatography (MPLC)

ORD record

ord-ad2aa245ba4b429eab8412cb8cb522c8

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586611B2