Reacción #49021

Ecuación de reacción

(E)-5-[(2-ethylcarbamoyl-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide

dichloroacetic acid

→

5-[(2-ethylcarbamoyl-ethoxyamino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide

Rendimiento 75.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for 1 hour
2. 2
   workup.ADDITIONthe reaction mixture was poured
3. 3
   Otrointo purified water
4. 4
   Extracciónthe resultant mixture was extracted with dichloromethane
5. 5
   SecadoThe combined organic layers were dried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

To (E)-5-[(2-ethylcarbamoyl-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (40 mg, 0.067 mmol) obtained in Step B was added dichloromethane (2 ml). The mixture was stirred at room temperature, and borane-pyridine complex (40 μl) and dichloroacetic acid (40 μl) were added thereto. After stirring for 1 hour, the reaction mixture was poured into purified water, and the resultant mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 5-[(2-ethylcarbamoyl-ethoxyamino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (C-18, 29 mg, 75% yield).

Fuente