Water → HCID 60196903, compound

HRID 878276Notes

Reaction equation

HRID 878276 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][C:5]1[CH:6]=[C:7]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:8]([N:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[O:25][CH3:26])[CH3:11])=[O:9].[OH:34]OS([O-])=O.[K+].[O-]S([O-])(=S)=O.[Na+].[Na+].CCOC(C)=O.[OH2:53]>CO>[NH2:1][CH2:2][CH2:3][S:4]([C:5]1[CH:6]=[C:7]([CH:27]=[C:28]([C:30]([F:32])([F:33])[F:31])[CH:29]=1)[C:8]([N:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[O:25][CH3:26])[CH3:11])=[O:9])(=[O:34])=[O:53]

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 70663436HCID 70663436, compound

Product 1

HCID 60196903HCID 60196903, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of 3-(2-aminoethylthio)-N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-5-(trifluoromethyl)benzamide (0.064 g, 133 μmol, example 237) in MeOH (2 mL) and water (0.5 mL) was added oxone (205 mg, 334 μmol) and the white suspension was stirred at room temperature for 4.5 hours. The reaction mixture was poured on 10% aqueous Na2S2O3 solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using an MPLC (Flasmaster) system eluting with a gradient of CH2Cl2:MeOH (100:0 to 85:15). Colorless solid (0.016 g; 23%). MS (ESI): m/z=512.13 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washThe organic layers were washed once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by silica gel chromatography on a 10 g column
  9. washeluting with a gradient of CH2Cl2:MeOH (100:0 to 85:15)

Sources & evidence

ORD record
ord-091e6b344bd04ef0aa69e1be62405fe6
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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