반응 #63920

반응 방정식

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

용매

dichloromethane

반응 조건

후처리

1. 1
   추출extracted with 150 ml portions of dichloromethane
2. 2
   기타The combined extracts were dried
3. 3
   농축concentrated 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
   추출extracted with 150 ml portions of dichloromethane
8. 8
   기타The combined extracts were dried
9. 9
   농축concentrated in vacuo
10. 10
    기타chromatographed on 300 g of silica gel with dichloromethane-methanol (97:3)
11. 11
    workup.ADDITIONThe fractions containing the desired product
12. 12
    농축concentrated in vacuo
13. 13
    기타the solid recrystallized from dichloromethane-hexane

실험 절차

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.

출처