2-Methyl-2-butene → 5-({2-[4-(2-tert-Butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carboxylic acid

HRID 534877Notes

Reaction equation

HRID 534877 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[CH2:18][S:19][C:20]2[N:24]([CH3:25])[N:23]=[C:22]([CH3:26])[C:21]=2[CH:27]=[O:28])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].P([O-])(O)(O)=[O:31].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].S([O-])(O)=O.[Na+]>O.C(O)(C)(C)C.O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:29])[CH2:18][S:19][C:20]2[N:24]([CH3:25])[N:23]=[C:22]([CH3:26])[C:21]=2[C:27]([OH:31])=[O:28])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 105532-Methyl-2-buteneHCID 23665763Sodium BisulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866633985-({2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 667927095-({2-[4-(2-tert-Butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carboxylic acidYield 59%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-({2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (900 mg), sodium dihydrogen phosphate (1.19 g), 2-methyl-2-butene (1.17 mL), tetrahydrofuran (10 mL), tert-butanol (3 mL), and water (1.5 mL) was added sodium chlorite (393 mg) at 0° C. and stirred at room temperature for 1 h. Aqueous sodium hydrogen sulfite was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (550 mg, 59%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c4cd66fef43c47e18b2e8f417acef297
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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