6-Chloro-(1,2,4)triazolo(1,5-b)pyridazine → HCID 21192626, compound

HRID 1169022Notes

Reaction equation

HRID 1169022 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].[Cl:30][C:31]1[CH:32]=[CH:33][C:34]2[N:35]([N:37]=[CH:38][N:39]=2)[N:36]=1>O1CCCC1>[ClH:30].[ClH:30].[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:31]3[CH:32]=[CH:33][C:34]4[N:35]([N:37]=[CH:38][N:39]=4)[N:36]=3)[CH2:12][CH2:13]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 112406116-Chloro-(1,2,4)triazolo(1,5-b)pyridazineHCID 155241464-Benzhydryl-1-piperazinepropanolHCID 23676156Sodium t-butoxide

Product 1

HCID 21192626HCID 21192626, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Diphenylmethyl)-1-piperazinepropanol (466 mg) was dissolved in dried tetrahydrofuran (10 ml), followed by addition of sodium t-butoxide (173 mg). The mixture was refluxed under, heating for 30 minutes. After the mixture was cooled, 6-chloro[1,2,4]triazolo[1,5-b ]pyridazine (268 mg) was added to the mixture. The resulting mixture was refluxed under heating for 3 hours. After the mixture was cooled, ice-water was added thereto, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride saturated solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with a mixture of ethyl acetate and methanol (10:1). Fractions containing the objective compound were collected and dissolved in ethyl acetate (10 ml), followed by addition of 4N HCl in ethyl acetate solution (0.7 ml). The resulting crystals were recrystallized from 95% aqueous ethanol to yield the title compound (413 mg).

Workup

  1. temperatureThe mixture was refluxed under,
  2. temperatureheating for 30 minutes
  3. temperatureAfter the mixture was cooled
  4. temperatureThe resulting mixture was refluxed
  5. temperatureunder heating for 3 hours
  6. temperatureAfter the mixture was cooled
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe extract was washed with an aqueous sodium chloride saturated solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washeluted with a mixture of ethyl acetate and methanol (10:1)
  12. additionFractions containing the objective compound
  13. customwere collected
  14. dissolutiondissolved in ethyl acetate (10 ml)
  15. additionfollowed by addition of 4N HCl in ethyl acetate solution (0.7 ml)
  16. customThe resulting crystals were recrystallized from 95% aqueous ethanol

Sources & evidence

ORD record
ord-443bd2cf58bd47108ba63aa1ca076047
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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