Réaction #1584

Équation de réaction

isopropyl 3-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]-pyridazin-1-ylidene)amino]phenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate

potassium carbonate

isopropyl bromoacetate

water

→

title product

Rendement 29.5%

Diisopropyl 5-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H, 3H-[1,3,4 ]thiadiazolo[3,4-a]pyridazin-1-ylidene) amino]phenyl}dihydro-2,4,6-trioxo-s-triazine-1,3 (2H,4H)-diacetate

Rendement 29.5%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   ExtractionThe aqueous mixture is extracted with ethyl acetate
2. 2
   ExtractionThe organic extract
3. 3
   Lavageis washed with brine
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Autreto obtain an orange gel

Mode opératoire

A mixture of isopropyl 3-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]-pyridazin-1-ylidene)amino]phenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.85 g, 1.62 mmol), potassium carbonate (0.27 g, 1.95 mmol) and isopropyl bromoacetate (0,353 g, 1.95 mmol)in N,N-dimethylformamide is stirred overnight at room temperature and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an orange gel. Flash column chromatography of the gel using silica gel and an ethyl acetate/hexanes solution (2:3) gives the title product as a yellow gel (0.3 g) which is identified by NMR spectral analysis.

Source