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

HRID 2424429Notes

Reaction equation

HRID 2424429 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C(#N)C>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 1

HCID 66849327N-(2-cyclopropylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (7.8 g, 34 mmol) and piperazine (8.93 g, 103 mmol) in acetonitrile (100 mL) was heated to refluxed for 2 hours. The solvent was removed by evaporation and the residue was dissolved in water (100 mL). The aqueous solution was extracted with dichloromethane (5×100 mL) and the organic extract was dried over anhydrous Na2SO4, filtered through a pad of silica gel and concentrated to give 6-piperazin-1-ylpyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (8.2 g, 88%). 1H NMR (300 MHz, CDCl3) δ 7.90-7.87, 6.89, 3.78-3.50, 3.12-2.90, 1.77-1.49, 0.83-0.60, 0.51-0.36, 0.15-0.01.

Workup

  1. temperatureto refluxed for 2 hours
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in water (100 mL)
  4. extractionThe aqueous solution was extracted with dichloromethane (5×100 mL)
  5. extractionthe organic extract
  6. dry with materialwas dried over anhydrous Na2SO4
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3b8168eb61c3485db8e9e2d4a3e349cb
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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