Reacción #88852

Ecuación de reacción

3-methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylic acid

4-benzyl-4-hydroxypiperidine

HATU

triethylamine

→

title compound

Rendimiento 62.8%

(4-benzyl-4-hydroxypiperidin-1-yl)(3-methyl-5-(pyridin-4-yl)-1,2-oxazol-4-yl)methanone

Rendimiento 62.8%

Disolventes

water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with ethyl acetate
2. 2
   LavadoThe extract was washed with saturated brine
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   OtroThe solvent was evaporated under reduced pressure
5. 5
   OtroThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
6. 6
   Otropurified by preparative HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA))
7. 7
   Concentraciónthe obtained fraction was concentrated under reduced pressure
8. 8
   workup.ADDITIONTo the residue was added saturated aqueous sodium hydrogen carbonate solution
9. 9
   Extracciónthe mixture was extracted with ethyl acetate
10. 10
    SecadoThe extract was dried over anhydrous sodium sulfate
11. 11
    Otrothe solvent was evaporated under reduced pressure

Procedimiento

A suspension of 3-methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylic acid (0.25 g), 4-benzyl-4-hydroxypiperidine (0.35 g), HATU (0.70 g) and triethylamine (0.85 mL) in DMF (5.0 mL) was stirred at room temperature for 3 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and then purified by preparative HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA)), and the obtained fraction was concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.29 g).

Fuente