Reaktion #2470639

Reaktionsgleichung

6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate

Hunig's Base

4-(3-isocyanatophenyl)-2-methylthiazole

→

N-(3-(2-methylthiazol-4-yl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

Ausbeute 71.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was then removed under reduced pressure
2. 2
   workup.ADDITIONfollowed by addition of 1 M Na2CO3 (5 mL) and EtOAc (10 mL)
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with water (3×10 mL)
5. 5
   workup.ADDITIONby adding water (10 mL)
6. 6
   SonstigeThe EtOAC was then removed under reduced pressure
7. 7
   Filtrationwas filtered
8. 8
   Waschenwashed with water
9. 9
   Sonstigedried under reduced pressure

Vorschrift

To a solution of 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate (0.100 g, 0.25 mmol) in THF (5 mL) and Hunig's Base (0.26 mL, 1.50 mmol) was added 4-(3-isocyanatophenyl)-2-methylthiazole (0.0567 g, 0.25 mmol). The reaction was shaken at room temperature for 2 hours. The solvent was then removed under reduced pressure followed by addition of 1 M Na2CO3 (5 mL) and EtOAc (10 mL). The organic layer was separated, washed with water (3×10 mL) followed by adding water (10 mL). The EtOAC was then removed under reduced pressure. A white solid crashed out which was filtered, washed with water, dried under reduced pressure to give the pure desired product, N-(3-(2-methylthiazol-4-yl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as a white solid (0.069 g, 71%).

Quelle