Reacción #44238

Ecuación de reacción

methyl 4-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate

O-(2-vinyloxy-ethyl)-hydroxylamine

LiHMDS

→

desired product

Rendimiento 99.0%

4-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridazine-3-carboxamide

Rendimiento 99.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was quenched with saturated aqueous NaHCO3
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   LavadoThe organic layer was washed with brine
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   Otroto give the crude material that
8. 8
   Otrowas purified by silica gel flash column chromatography (100% CH2Cl2 to 1.5% MeOH in CH2Cl2)

Procedimiento

To a solution of methyl 4-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate (25 mg, 0.077 mmol) and O-(2-vinyloxy-ethyl)-hydroxylamine (24 mg, 0.23 mmol) in THF (2 mL) at 0° C. was added LiHMDS (0.54 mL, 0.54 mmol, 1 M in THF). The reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was quenched with saturated aqueous NaHCO3 and diluted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (100% CH2Cl2 to 1.5% MeOH in CH2Cl2) to afford 30 mg (99%) of the desired product.

Fuente