Water → HCID 70663407, compound

HRID 878307Notes

Reaction equation

HRID 878307 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:35])[C:15](=[O:34])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([S:26][CH2:27][CH2:28][NH:29][S:30](=[O:33])(=[O:32])[NH2:31])[CH:17]=2)=[C:4]([O:36][CH3:37])[CH:3]=1.[OH:38]OS([O-])=O.[K+].[O-]S([O-])(=S)=O.[Na+].[Na+].CCOC(C)=O.[OH2:57]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:35])[C:15](=[O:34])[C:16]2[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[C:18]([S:26]([CH2:27][CH2:28][NH:29][S:30](=[O:32])(=[O:33])[NH2:31])(=[O:38])=[O:57])[CH:17]=2)=[C:4]([O:36][CH3:37])[CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 70663176HCID 70663176, compound

Product 1

HCID 70663407HCID 70663407, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-3-(2-(sulfamoylamino)ethylthio)-5-(trifluoromethyl)benzamide (0.058 g, 104 μmol, example 261) in MeOH (2 mL) and water (0.5 mL) was added oxone (160 mg, 260 μmol) and the white suspension was stirred at room temperature for 3.5 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 crude product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless solid (0.047 g; 76%). MS (ESI): m/z=591.10 [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 crude product was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-636009dc9ee54c03be0b986fb4a4ea76
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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