Reaktion #71997

Reaktionsgleichung

Methyl chloroglyoxylate

triethylamine

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

→

title compound

Ausbeute 90.7%

Methyl cis(±)-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)(oxo)acetate

Ausbeute 90.7%

Lösungsmittel

ethyl acetate

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Waschenwashed with water and brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Einengenconcentration under reduced pressure
5. 5
   Sonstigethe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=7/3→1/0)

Vorschrift

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (200 mg, 0.593 mmol) was suspended in dichloromethane (5 mL). Methyl chloroglyoxylate (0.070 mL, 0.76 mmol), triethylamine (0.250 mL, 1.80 mmol) and DMAP (catalytic amount) were added under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=7/3→1/0) to obtain 208.1 mg of the title compound as a colorless oily substance (91%).

Quelle