Piperazine → HCID 66849763, compound

HRID 2424436Notes

Reaction equation

HRID 2424436 reaction equation
[CH2:1]([NH:6][C:7]([C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=1)=[O:8])[CH2:2][CH2:3][CH:4]=[CH2:5].[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C(#N)C>[CH2:1]([NH:6][C:7]([C:9]1[N:10]=[N:11][C:12]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:13][CH:14]=1)=[O:8])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 86025942HCID 86025942, compound

Product 1

HCID 66849763HCID 66849763, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-chloropyridazine-3-carboxylic acid pent-4-enylamide synthesized above (1.08 g, 4.79 mmol) in acetonitrile (39 mL) was added piperazine (1.25 g, 14.5 mmol). The reaction mixture was heated to reflux overnight (TLC indicated the reaction was complete). The mixture was evaporated and the solid residue was dissolved in a mixture of ethyl acetate (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined ethyl acetate layer were dried over Na2SO4 and concentrated to yield the title compound as a yellow solid (1.169 g, 88.6% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight (TLC
  3. customThe mixture was evaporated
  4. dissolutionthe solid residue was dissolved in a mixture of ethyl acetate (100 mL) and water (100 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. dry with materialThe combined ethyl acetate layer were dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f8dc0c959ce244dd80b22232aff05998
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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