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

HRID 734262Notes

Reaction equation

HRID 734262 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:7]1([CH2:10][CH2:11][NH:12][C:13]([C:15]2[N:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=2)=[O:14])[CH2:9][CH2:8]1>C(#N)C.ClCCl>[CH:7]1([CH2:10][CH2:11][NH:12][C:13]([C:15]2[N:16]=[N:17][C:18]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)=[CH:19][CH:20]=2)=[O:14])[CH2:9][CH2:8]1

Participants

5

Reactant 2

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

Product 1

HCID 66849327N-(2-cyclopropylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamideYield 75%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of piperazine (1.48 g, 17.2 mmol) and 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (1.29 g, 5.73 mmol) in acetonitrile (60 mL) was heated at reflux for 16 hours. After the reaction mixture was cooled, the gummy material was diluted with dichloromethane (50 mL), washed with water (2×20 mL), dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The crude material was purified by column chromatography eluting with dichloromethane (100%) then with methanol:dichloromethane (1:9) to obtain 1.18 g (75%) of the product as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter the reaction mixture was cooled
  4. washwashed with water (2×20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe crude material was purified by column chromatography
  9. washeluting with dichloromethane (100%)

Sources & evidence

ORD record
ord-6f71a77c56ed45f181cb46d46c3c9c22
Source dataset
uspto-grants-2009_09
Patent number
US07592343B2

Reaction notes

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