Methanol → {4-[6-(2-Phenylethanesulfinyl)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanone

HRID 1684994Notes

Reaction equation

HRID 1684994 reaction equation
I([O-])(=O)(=O)=O.[Na+].C[OH:8].[CH2:9]([S:17][C:18]1[N:23]=[N:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]([F:41])([F:40])[F:39])=[O:31])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[C:11]1([CH2:10][CH2:9][S:17]([C:18]2[N:23]=[N:22][C:21]([N:24]3[CH2:25][CH2:26][N:27]([C:30]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[C:38]([F:41])([F:40])[F:39])=[O:31])[CH2:28][CH2:29]3)=[CH:20][CH:19]=2)=[O:8])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11155686[4-(6-Phenethylsulfanylpyridazin-3-YL)piperazin-1-YL](2-trifluoromethylphenyl)methanoneHCID 23667635Sodium periodate

Product 1

HCID 11179294{4-[6-(2-Phenylethanesulfinyl)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanoneYield 69.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To an ice-cold solution of sodium periodate (0.025 g, 0.12 mmol) in 1:1 mixture of water and methanol was added [4-(6-phenethylsulfanylpyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone. The reaction mixture was stirred at room temperature over night, diluted with water and then extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous MgSO4 and then concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a white solid (41 mg, 69.2%). 1H NMR (400 MHz, CDCl3) δ 7.86, 7.75, 7.63-7.66, 7.56-7.59, 7.37, 7.25-7.28, 7.21-7.17, 7.07-7.09, 4.04-4.10, 3.83-3.91, 3.70-3.80, 3.45-3.35, 3.26-3.30, 3.2-3.15.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9f61b40927e548a4bbaafdd1e970d17b
Source dataset
uspto-grants-2012_04
Patent number
US08148378B2

Reaction notes

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