Reaktion #45087

Reaktionsgleichung

Trimethylaluminium

5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine

methyl 5-chloropyrazine-2-carboxylate

toluene

→

desired compound

Ausbeute 63.0%

5-(1,3,4,6,7,8,9,9a-Octahydropyrido[2,1-c]pyrazin-2-yl)-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide

Ausbeute 63.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas increased to 60° C.
2. 2
   workup.STIRRINGthe reaction mixture was stirred for a further 3 h
3. 3
   SonstigeThe reaction mixture was quenched with methanol (10 mL) and HCl (2M aqueous solution)
4. 4
   workup.ADDITIONThe mixture was diluted with EtOAc (100 mL) and water (250 mL)
5. 5
   SonstigeThe organic layer was removed
6. 6
   Extraktionthe aqueous further extracted with EtOAc (2×100 mL)
7. 7
   WaschenThe combined organics were washed with water (200 mL), brine (200 mL)
8. 8
   Trocknendried over MgSO4
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    EinengenUpon concentration a precipitate
11. 11
    Sonstigeformed
12. 12
    FiltrationThe precipitate was collected by filtration
13. 13
    Waschenwashed with MeOH (10 mL) and air
14. 14
    Sonstigedried

Vorschrift

Trimethylaluminium (2M in toluene, 9.64 ml, 19.28 mmol) was added dropwise to a stirred suspension of 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (1.91 g, 7.71 mmol) and methyl 5-chloropyrazine-2-carboxylate (1.33 g, 7.71 mmol) in anhydrous toluene (38.6 ml) at ambient temperature. The resulting solution was then stirred under nitrogen at ambient temperature for 18 h. The reaction was incomplete so the temperature was increased to 60° C. and the reaction mixture was stirred for a further 3 h. The reaction mixture was quenched with methanol (10 mL) and HCl (2M aqueous solution). The mixture was diluted with EtOAc (100 mL) and water (250 mL) and then acidified with HCl (2N aqueous solution). The organic layer was removed and the aqueous further extracted with EtOAc (2×100 mL). The combined organics were washed with water (200 mL), brine (200 mL) dried over MgSO4 and concentrated under reduced pressure. Upon concentration a precipitate formed. The precipitate was collected by filtration, washed with MeOH (10 mL) and air dried to afford the desired compound (1.88 g, 63%) as a yellow solid, which was used without further purification.

Quelle