Difluoroacetic acid → 6-Chloro-3-(difluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1674760

Reaction equation

HRID 1674760 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:8][NH2:9])=[CH:6][CH:7]=1.[F:10][CH:11]([F:15])[C:12](O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:4]([C:12]([CH:11]([F:15])[F:10])=[N:9][N:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 9788Difluoroacetic acidHCID 1007873-Chloro-6-hydrazinopyridazine

Product 1

HCID 14723856-Chloro-3-(difluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazineYield 84.7%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-chloropyridazin-6-yl hydrazine (5.0 g, 34.72 mmol) and difluoroacetic acid (21.93 mL; ca. 347 mmol) was heated at 100° C. for 3 hours and then evaporated to dryness. The involatile residue was dissolved in ethyl acetate (200 mL) and washed sequentially with saturated aqueous sodium carbonate and then saturated brine. The organic phase was dried over MgSO4, filtered, and evaporated to give 6-chloro-3-difluoromethyl-[1,2,4]-triazolo[4,3-b]pyridazine (6.0 g, 84.7%) as a white solid that was used without further purification.

Workup

  1. customevaporated to dryness
  2. dissolutionThe involatile residue was dissolved in ethyl acetate (200 mL)
  3. washwashed sequentially with saturated aqueous sodium carbonate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0ceaf4b1da1f4d33957a3227a815b9d9
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Linked notes

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