反応 #63920

反応方程式

sodium bicarbonate

3-methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

diisopropylamine

4-chlorobutyryl chloride

→

white crystals

1-[3-(3-Methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]-2-pyrolidinone

溶媒

dichloromethane

反応条件

後処理

1. 1
   抽出extracted with 150 ml portions of dichloromethane
2. 2
   その他The combined extracts were dried
3. 3
   濃縮concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in 200 ml of dimethylformamide
5. 5
   workup.ADDITION2.0 g of potassium carbonate was added
6. 6
   workup.ADDITIONpoured onto 200 ml of water
7. 7
   抽出extracted with 150 ml portions of dichloromethane
8. 8
   その他The combined extracts were dried
9. 9
   濃縮concentrated in vacuo
10. 10
    その他chromatographed on 300 g of silica gel with dichloromethane-methanol (97:3)
11. 11
    workup.ADDITIONThe fractions containing the desired product
12. 12
    濃縮concentrated in vacuo
13. 13
    その他the solid recrystallized from dichloromethane-hexane

実験手順

To a solution of 2 g of 3-methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine in 400 ml of dichloromethane was added 1.7 ml of diisopropylamine and 1 ml of 4-chlorobutyryl chloride. This solution was stirred for 12 hours, then poured onto 200 ml of saturated aqueous sodium bicarbonate and extracted with 150 ml portions of dichloromethane. The combined extracts were dried and concentrated in vacuo. The residue was dissolved in 200 ml of dimethylformamide and 2.0 g of potassium carbonate was added. This solution was heated to 80° C. for 12 hours, then poured onto 200 ml of water and extracted with 150 ml portions of dichloromethane. The combined extracts were dried, concentrated in vacuo and chromatographed on 300 g of silica gel with dichloromethane-methanol (97:3). The fractions containing the desired product were combined, concentrated in vacuo and the solid recrystallized from dichloromethane-hexane to give 1.67 g of white crystals, mp 235°-237° C.

出典