Trifluoroacetic acid → 6-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine

HRID 1674762Notes

Reaction equation

HRID 1674762 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:33])([F:32])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1.C(=O)(O)[O-].[Na+]>ClCCl>[N:19]1([C:16]2[CH:17]=[CH:18][C:13]3[N:14]([C:10]([C:9]([F:8])([F:32])[F:33])=[N:11][N:12]=3)[N:15]=2)[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 46681952HCID 46681952, compound

Product 1

HCID 14768626-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (25 mL, 324.49 mmol) was added to a mixture of tert-butyl 4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperazine-1-carboxylate (6.7 g, 17.99 mmol) and dichloromethane (100 mL) at ambient temperature and the resulting solution was stirred at ambient temperature for 1 hour. The reaction mixture was evaporated to give an involatile residue that was treated with saturated aqueous sodium bicarbonate solution (100 mL) and then extracted with dichloromethane (4×200 mL). The organic phases were combined and dried over Na2SO4, filtered, and evaporated to give 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (4.78 g, 98%) as a white solid that was used without further purification.

Workup

  1. customThe reaction mixture was evaporated
  2. customto give an involatile residue that
  3. extractionextracted with dichloromethane (4×200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e2b5adbbe38f4bd38d47c310d5bec243
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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