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

HRID 35655

Reaction equation

HRID 35655 reaction equation
[CH2:1]([N:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=2)[CH:9]=1)[C:4](=[O:7])[CH2:5][CH3:6])[CH3:2].[NH2:21][NH:22][C:23]([NH2:25])=S>C(O)C>[CH2:1]([N:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]3[N:16]([C:23]([NH2:25])=[N:22][N:21]=3)[N:15]=2)[CH:9]=1)[C:4](=[O:7])[CH2:5][CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 14280299N-ethyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]propanamide

Product 1

HCID 15595696N-Ethyl-N-[3-(3-amino-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]propanamideYield 44.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.0 g N-ethyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]propanamide and 3.2 g thiosemicarbazide in 200 ml ethanol was refluxed for 18 hours. The mixture was treated and the product chromatographed as described for Example 70. Recrystalization of the product from dichloromethane-hexane afforded 2.4 g yellow crystals, mp 199°-200° C.

Workup

  1. additionThe mixture was treated
  2. customthe product chromatographed
  3. customRecrystalization of the product from dichloromethane-hexane

Sources & evidence

ORD record
ord-2860d62b5c8c430fa9b9be9aaab6cc24
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Linked notes

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