Reacción #74678

Ecuación de reacción

5-chloro-4-(4-chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenoxy)-2-fluoro-N-(methoxymethyl)-N-(pyrimidin-4-yl)benzenesulfonamide

ethanol

ammonium chloride

→

colorless oil

Rendimiento 97.8%

4-{2-[3-amino-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-chlorophenoxy}-5-chloro-2-fluoro-N-(methoxymethyl)-N-pyrimidin-4-ylbenzenesulfonamide

Rendimiento 97.8%

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthen filtered
2. 2
   workup.ADDITIONSaturated aqueous sodium bicarbonate was added until the pH was 9
3. 3
   ConcentraciónThe mixture was concentrated in vacuo
4. 4
   Otroto remove the ethanol
5. 5
   workup.ADDITIONWater was added
6. 6
   Extracciónthe mixture was extracted three times with dichloromethane
7. 7
   SecadoThe combined organic phase was dried over anhydrous sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated in vacuo
10. 10
    OtroThe residue was purified on silica gel (hexane to 100% ethyl acetate gradient)

Procedimiento

To a solution of 5-chloro-4-(4-chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenoxy)-2-fluoro-N-(methoxymethyl)-N-(pyrimidin-4-yl)benzenesulfonamide (80 mg, 0.1 mmol) in ethanol (4 mL, 70 mmol) was added saturated aqueous ammonium chloride solution (0.4 mL, 6 mmol) and iron (328 mg, 5.87 mmol). The reaction solution was heated at 80° C. for 20 minutes then filtered. Saturated aqueous sodium bicarbonate was added until the pH was 9. The mixture was concentrated in vacuo to remove the ethanol. Water was added and the mixture was extracted three times with dichloromethane. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified on silica gel (hexane to 100% ethyl acetate gradient) to give 61 mg of a colorless oil.

Fuente