反应详情

温度

50 °C

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).

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