2,5-Dimethylpiperazine → HCID 67010994, compound

HRID 2354814Notes

Reaction equation

HRID 2354814 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][CH2:4][CH3:5].[CH3:16][CH:17]1[CH2:22][NH:21][CH:20]([CH3:23])[CH2:19][NH:18]1.C(N(CC)CC)C.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>CC(O)C.ClCCl>[CH2:1]([NH:6][C:7]([C:9]1[N:10]=[N:11][C:12]([N:18]2[CH2:19][CH:20]([CH3:23])[N:21]([C:35](=[O:36])[C:34]3[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=3[C:32]([F:31])([F:42])[F:43])[CH2:22][CH:17]2[CH3:16])=[CH:13][CH:14]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 78162,5-Dimethylpiperazine2×HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 442031536-Chloropyridazine-3-carboxylic acid pentylamide

Product 1

HCID 67010994HCID 67010994, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 6-chloropyridazine-3-carboxylic acid pentylamide (304 mg, 1.00 mmol) in 2-propanol (12 mL) was added 2,5-dimethylpiperazine (1.37 g, 12.0 mmol). The reaction mixture was refluxed for 2 days. Another 0.25 g of 2,5-dimethylpiperazine and 1.0 mL of triethylamine were added to the reaction mixture and heating was continued for another 24 hours. After the reaction mixture was cooled to ambient temperature and the solvent was removed by rotary evaporator. To the dichloromethane solution of the crude material (20 mL) was added the solution of 2-trifluoromethylbenzoyl chloride (0.63 g, 3.00 mmol) in dichloromethane (20 mL) and the reaction mixture was stirred at ambient temperature for 16 hours. The organic layer was diluted with dichloromethane (50 mL) and then washed with 10% HCl, dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The crude material was purified by column chromatography eluting with ethyl acetate (100%) to afford 300 mg (31% yield) of the product as a colourless solid. 1H NMR (300 MHz, CDCl3) δ 7.74-7.43, 7.36-7.24, 5.17-5.04, 4.91-4.79, 4.52, 4.52, 3.68-3.57, 3.54-3.44, 3.39-3.11, 2.93, 2.85-2.71, 1.36-1.31, 1.27-1.15, 1.23-1.05.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days
  2. temperatureheating
  3. customthe solvent was removed by rotary evaporator
  4. washwashed with 10% HCl
  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 ethyl acetate (100%)

Sources & evidence

ORD record
ord-6dbf95947dfe47b19b71a59b8636e678
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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