Réaction #531884

Équation de réaction

ethyl (2Z)-2-cyano-3-[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl]-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylate

ethylamine

AlMe3

→

(2Z)-2-cyano-N-cyclopropyl-3-[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl]-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylamide

Rendement 54.2%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was quenched with aqueous saturated NH4Cl
2. 2
   Extractionextracted with ethylacetate
3. 3
   Séchagedried over MgSO4
4. 4
   Concentrationconcentrated under vacuum
5. 5
   AutreThe residue was purified by chromatography on silica gel

Mode opératoire

A solution of ethyl (2Z)-2-cyano-3-[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl]-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylate (0.122 g, 0.32 mmol, 1 eq.) in 3 ml of toluene was treated with ethylamine (1 M solution in tetrahydrofurane, 0.96 ml, 0.96 mmol, 3 eq.) and AlMe3 (1 M solution in toluene, 0.96 ml, 0.96 mmol, 3 eq.). The reaction was microwaved at 110° C. for 1800s (fixed hold, high absorption). The reaction was quenched with aqueous saturated NH4Cl and extracted with ethylacetate. The organic layers were combined and dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel to give (2Z)-2-cyano-N-cyclopropyl-3-[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl]-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylamide (0.068 g, 51% yield) as a mixture of atropoisomers.

Source