Piperazine → 6-Piperazin-1-yl-pyridazin-3-carboxylic acid (3-methylbutyl)amide

HRID 2424428Notes

Reaction equation

HRID 2424428 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=1)=[O:7].[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C(#N)C>[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:13]=1)=[O:7]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 167337866-chloro-N-(3-methylbutyl)pyridazine-3-carboxamide

Product 1

HCID 668493226-Piperazin-1-yl-pyridazin-3-carboxylic acid (3-methylbutyl)amideYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-chloropyridazine-3-carboxylic acid (3-methylbutyl)amide (2.52 g, 11.0 mmol) and piperazine (2.83 g, 32.8 mmol) in acetonitrile (30 mL) was heated to refluxed for 2 hours. The solvent was removed by evaporation, the residue was dissolved in water (50 ml) and extracted with dichloromethane (3×100 mL). The organic extract was dried over anhydrous Na2SO4 and then evaporated. The residue was passed through a pad of silica gel and concentrated to give 6-piperazin-1-yl-pyridazine-3-carboxylic acid (3-methylbutyl)amide (2.68 g, 88% yield). MS (ES+) m/z 278 (M+1).

Workup

  1. temperatureto refluxed for 2 hours
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in water (50 ml)
  4. extractionextracted with dichloromethane (3×100 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous Na2SO4
  7. customevaporated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-60e2f515b32e460897ee8980fa53b3ab
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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