Potassium Carbonate → {4-[6-(Methylphenethylamino)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanone

HRID 1684991Notes

Reaction equation

HRID 1684991 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:26][NH:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[NH4+].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[CH3:26][N:27]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11503N-MethylbenzeneethanamineHCID 25517Ammonium ChlorideHCID 86024941HCID 86024941, compound

Product 1

HCID 11167288{4-[6-(Methylphenethylamino)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanoneYield 11%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of [4-(6-chloropyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone (0.072 g, 0.194 mmol), N-methyl-2-phenylethylamine (0.052 g, 0.388 mmol), ammonium chloride (0.01 g, 0.194 mmol) in n-butanol (4 mL) was refluxed for 48 hours. The reaction mixture was cooled to room temperature, then added 10% potassium carbonate solution, and extracted with ethyl acetate. The organic extract was dried over anhydrous Na2SO4, and then concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a white solid (10 mg, 11% yield). 1H NMR (400 MHz, CDC3) δ 7.73, 7.61-7.64, 7.53-7.56, 7.36, 7.26-7.29, 7.19-7.21, 6.91, 6.75, 3.95, 3.75, 3.30-3.50, 0.92. MS (ES+) m/z 470.3 (M+1).

Workup

  1. temperaturewas refluxed for 48 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b0eacfc4e9844d858a9f6c3c5914d118
Source dataset
uspto-grants-2012_04
Patent number
US08148378B2

Reaction notes

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