Reacción #68653

Ecuación de reacción

8-chloro-1,5-naphthyridin-3-amine

triethylamine

2-methoxyacetyl chloride

→

N-(8-chloro-1,5-naphthyridin-3-yl)-2-methoxyacetamide

Rendimiento 75.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroreaction
2. 2
   OtroNext day reaction mixture
3. 3
   Lavadowashed with aqueous sodium bicarbonate solution
4. 4
   OtroLayers separated
5. 5
   Secadoorganic layer dried over sodium sulfate
6. 6
   Otroto afford yellow oil
7. 7
   OtroThis was purified by ISCO silica gel chromatography (2-5% MeOH/DCM)

Procedimiento

A round bottom flask under nitrogen was charged with 8-chloro-1,5-naphthyridin-3-amine (41 mg, 0.23 mmol), triethylamine (64 μl, 0.46 mmol), and dichloromethane (1 mL). To this was added 2-methoxyacetyl chloride (42 μl, 0.46 mmol) dropwise via syringe and reaction allowed to stir overnight at room temperature. Next day reaction mixture was diluted with dichloromethane and washed with aqueous sodium bicarbonate solution. Layers separated and organic layer dried over sodium sulfate to afford yellow oil. This was purified by ISCO silica gel chromatography (2-5% MeOH/DCM) to afford N-(8-chloro-1,5-naphthyridin-3-yl)-2-methoxyacetamide (43 mg, 75% yield) as light yellow solid. MS[M+H]=251.9. Calc'd for C11H10ClN3O2=251.7.

Fuente