Acetic Acid → HCID 86711641, compound

HRID 527375Notes

Reaction equation

HRID 527375 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[S:33]([CH3:37])=[N:34][C:35]#[N:36])[CH2:5][NH:6][C:7]([C:9]1[C:14](=[O:15])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:12]([CH3:26])[N:11]([CH:27]([CH3:29])[CH3:28])[CH:10]=1)=[O:8].C(O)(=[O:40])C.[Mn]([O-])(=O)(=O)=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[S:33]([CH3:37])(=[N:34][C:35]#[N:36])=[O:40])[CH2:5][NH:6][C:7]([C:9]1[C:14](=[O:15])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:12]([CH3:26])[N:11]([CH:27]([CH3:29])[CH3:28])[CH:10]=1)=[O:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24477Sodium ThiosulfateHCID 516875Potassium Permanganate2×HCID 86711639HCID 86711639, compound

Product 1

HCID 86711641HCID 86711641, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 1-isopropyl-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 3-methyl-4-(N-cyano-S-methylsulfinimidoyl)-benzylamide (preparation 66d, 25 mg, 47 μmol) and acetic acid (3 μL, 50 μmol) in acetonitrile (0.2 mL) is added to a solution of potassium permanganate (8 mg, 50 μmol) in acetonitrile (0.15 mL) and water (0.15 mL). After 3 h another portion of potassium permanganate (8 mg, 50 μmol) is added and the mixture is heated at reflux. After 2 h saturated aqueous sodium thiosulfate solution is added, and the mixture is extracted twice with dichloromethane. The organic layer is dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by preparative reversed phase HPLC (Xbridge, gradient of acetonitrile in water, 0.1% TFA). Yield: 2 mg (8% of theory); ESI mass spectrum: [M+H]+=545; r.t. HPLC: 0.61 min (X012_S01).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux
  3. extractionthe mixture is extracted twice with dichloromethane
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by preparative reversed phase HPLC (Xbridge, gradient of acetonitrile in water, 0.1% TFA)
  7. customr.t
  8. custom0.61 min (X012_S01)

Sources & evidence

ORD record
ord-00c69945ba7d469ca323a762666c6918
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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