Piperazine → N-(2-Cyclobutylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamide

HRID 2356402Notes

Reaction equation

HRID 2356402 reaction equation
[CH:1]1([CH2:5][CH2:6][NH:7][C:8]([C:10]2[N:11]=[N:12][C:13](Cl)=[CH:14][CH:15]=2)=[O:9])[CH2:4][CH2:3][CH2:2]1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(#N)C>[CH:1]1([CH2:5][CH2:6][NH:7][C:8]([C:10]2[N:11]=[N:12][C:13]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:14][CH:15]=2)=[O:9])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 860260456-CHLOROPYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOBUTYLETHYL)AMIDE

Product 1

HCID 66849365N-(2-Cyclobutylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamideYield 78.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-chloropyridazine-3-carboxylic acid (2-cyclobutylethyl)-amide (1.2 g, 5.00 mmol) in acetonitrile (40 mL) was added piperazine (1.29 g, 15.00 mmol). The reaction mixture was heated to reflux overnight. The mixture was evaporated and the solid residue was taken in ethyl acetate (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined ethyl acetates were dried over Na2SO4 and concentrated in vacuo to give the title compound as yellow solid (1.14 g, 78.4% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe mixture was evaporated
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  6. dry with materialThe combined ethyl acetates were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92b591e2026b4ab3b4eb0545bec7b797
Source dataset
uspto-grants-2010_07
Patent number
US07759348B2

Reaction notes

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