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

HRID 1906798Notes

Reaction equation

HRID 1906798 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=2)[CH:7]=1)[C:3](=[O:5])[CH3:4].[NH2:19][NH:20][C:21]([NH2:23])=S>C(O)C>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]3[N:14]([C:21]([NH2:23])=[N:20][N:19]=3)[N:13]=2)[CH:7]=1)[C:3](=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 15595702N-Methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

Product 1

HCID 15595668N-Methyl-N-[3-(3-amino-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamideYield 25.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.2 g of N-methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide and 1.5 g of thiosemicarbazide in 100 ml of ethanol was refluxed for 5 hours, then the solvent was removed in vacuo. To the residue was added 100 ml of glacial acetic acid, this mixture was refluxed 18 hours, then the acetic acid was removed in vacuo. Saturated aqueous sodium bicarbonate was added to neutralize the mixture which was then extracted with dichloromethane:methanol (9:1). The extract was washed with water, dried and evaporated. The residue was chromatographed on a silica gel column, eluting with dichloromethane:methanol (9:1). The product was crystallized from dichloromethane-hexane, giving 0.6 g of the desired compound as yellow crystals mp 196°-197° C.

Workup

  1. customthe solvent was removed in vacuo
  2. additionTo the residue was added 100 ml of glacial acetic acid
  3. temperaturethis mixture was refluxed 18 hours
  4. customthe acetic acid was removed in vacuo
  5. additionSaturated aqueous sodium bicarbonate was added
  6. extractionwas then extracted with dichloromethane:methanol (9:1)
  7. washThe extract was washed with water
  8. customdried
  9. customevaporated
  10. customThe residue was chromatographed on a silica gel column
  11. washeluting with dichloromethane:methanol (9:1)
  12. customThe product was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-7f0e3cd45166435a8e100a622b4af6f6
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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