Triethylamine → HCID 86719954, compound

Participants

Reaction Steps

To a solution of [3,5-bis-(difluoromethyl)-1H-pyrazol-1-yl]acetic acid (2 g) in dichloromethane (40 ml) are added, at 0° C., oxalyl chloride (3.273 g) and one drop of N,N-dimethylformamide. The reaction mixture is stirred at room temperature for 2 hours. The solvent and the excess reagent are removed under reduced pressure. The solid residue is again dissolved in dichloromethane (15 ml) and, at 0° C., added dropwise to a solution of 4-{4-[5-(2,6-difluoro-3-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidinium chloride (compound A) and triethylamine (5.0 eq.) in dichloromethane (100 ml). The reaction mixture is stirred at room temperature overnight. Then it is admixed with concentrated sodium hydrogencarbonate solution, and the aqueous phase is removed and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated. Purification by column chromatography gives 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-(2,6-difluoro-3-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (1.818 g).

Provenance & Evidence