Reaktion #68454

Reaktionsgleichung

diethylazodicarboxylate

N′-(6-chloropyridazin-3-yl)-2-(7-methoxyquinolin-4-yloxy)acetohydrazide

triphenylphosphine

trimethylsilyl azide

→

4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated in vacuo
2. 2
   SonstigeThe remaining oil was triturated with diethyl ether
3. 3
   SonstigeA gel-like solid formed which
4. 4
   Sonstigewas collected on a glass frit
5. 5
   Waschenwashing with diethyl ether
6. 6
   SonstigeThe solid was then triturated with ethyl acetate, and finally acetonitrile
7. 7
   SonstigeAn amorphous solid formed which
8. 8
   Sonstigewas collected on a glass frit
9. 9
   Waschenwashing with acetonitrile
10. 10
    SonstigeThe solid was further dried under high vacuum
11. 11
    EinengenIn addition, the ethyl acetate filtrate was concentrated in vacuo
12. 12
    SonstigeThe remaining oil was then triturated with acetonitrile
13. 13
    SonstigeAn amorphous solid formed
14. 14
    Sonstigewas collected on a glass frit
15. 15
    Waschenwashing with acetonitrile
16. 16
    SonstigeThe solid was further dried under high vacuum

Vorschrift

N′-(6-chloropyridazin-3-yl)-2-(7-methoxyquinolin-4-yloxy)acetohydrazide (2.53 g, 7.0 mmol) was suspended in tetrahydrofuran (50 mL) then added triphenylphosphine (2.8 g, 11 mmol) and trimethylsilyl azide (1.4 ml, 11 mmol). To this suspension, was added diethylazodicarboxylate (2.0 ml, 13 mmol) in rapid drops with a syringe. The mixture became clear and hot to the touch. The reaction mixture was heated at 50° C. for 30 minutes. The reaction mixture was concentrated in vacuo. The remaining oil was triturated with diethyl ether. A gel-like solid formed which was collected on a glass frit, washing with diethyl ether. The solid was then triturated with ethyl acetate, and finally acetonitrile. An amorphous solid formed which was collected on a glass frit, washing with acetonitrile. The solid was further dried under high vacuum. In addition, the ethyl acetate filtrate was concentrated in vacuo. The remaining oil was then triturated with acetonitrile. An amorphous solid formed and was collected on a glass frit, washing with acetonitrile. The solid was further dried under high vacuum affording 4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline as a tan solid. MS (ESI, pos. ion) m/z: 342.1 (M+1).

Quelle