Thiosemicarbazide → N-Ethyl-N-[3-(3-amino-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide

HRID 329629Notes

Reaction equation

HRID 329629 reaction equation
[CH2:1]([N:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=2)[CH:8]=1)[C:4](=[O:6])[CH3:5])[CH3:2].[NH2:20][NH:21][C:22]([NH2:24])=S>C(O)C>[CH2:1]([N:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]3[N:15]([C:22]([NH2:24])=[N:21][N:20]=3)[N:14]=2)[CH:8]=1)[C:4](=[O:6])[CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 14280297N-Ethyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

Product 1

HCID 15595669N-Ethyl-N-[3-(3-amino-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.0 g of N-ethyl-N-[3-(6-chloro-3pyridazinyl)phenyl]acetamide and 1.32 g of thiosemicarbazide in 100 ml of ethanol was refluxed for 8 hours, then evaporated in vacuo. To the residue was added 100 ml of glacial acetic acid. This mixture was refluxed overnight, then the solvent was removed in vacuo, 150 ml of water added and aqueous sodium bicarbonate added to neutralize the solution. This mixture was extracted with dichloromethane:methanol (9:1). The extracts were dried and evaporated. The residue was chromatographed on a silica gel column eluting with dichloromethane:methanol (9:1). The fractions containing product were combined and evaporated.

Workup

  1. customevaporated in vacuo
  2. additionTo the residue was added 100 ml of glacial acetic acid
  3. temperatureThis mixture was refluxed overnight
  4. customthe solvent was removed in vacuo, 150 ml of water
  5. additionadded
  6. additionaqueous sodium bicarbonate added
  7. extractionThis mixture was extracted with dichloromethane:methanol (9:1)
  8. customThe extracts were dried
  9. customevaporated
  10. customThe residue was chromatographed on a silica gel column
  11. washeluting with dichloromethane:methanol (9:1)
  12. additionThe fractions containing product
  13. customevaporated

Sources & evidence

ORD record
ord-86d1ab1d9cd24198898346a4b1fc3433
Source dataset
uspto-grants-1990_01
Patent number
US04892873

Reaction notes

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