Water → HCID 70663236, compound

HRID 878320Notes

Reaction equation

HRID 878320 reaction equation
[NH:1]1[CH2:4][CH:3]([S:5][C:6]2[CH:7]=[C:8]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=2)[C:9]([N:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[O:26][CH3:27])[CH3:12])=[O:10])[CH2:2]1.[OH:35]OS([O-])=O.[K+].[O-]S([O-])(=S)=O.[Na+].[Na+].CCOC(C)=O.[OH2:54]>CO>[NH:1]1[CH2:4][CH:3]([S:5]([C:6]2[CH:7]=[C:8]([CH:28]=[C:29]([C:31]([F:32])([F:34])[F:33])[CH:30]=2)[C:9]([N:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[O:26][CH3:27])[CH3:12])=[O:10])(=[O:35])=[O:54])[CH2:2]1

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 60196597HCID 60196597, compound

Product 1

HCID 70663236HCID 70663236, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of 3-(azetidin-3-ylthio)-N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-5-(trifluoromethyl)benzamide (0.257 g, 523 μmol, example 275) in MeOH (6 mL) and water was added Oxone® (804 mg, 1.31 mmol) and stirring was continued 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 saturated with sodium chloride, extracted eight times with EtOAc. The organic layers were washed once with brine, dried over MgSO4, filtered and evaporated. The product (43 mg) was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.05% triethylamine) (20:80 to 98:2). Colorless solid (0.135 g; 49%). MS (ESI): m/z=524.13 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionextracted eight times with EtOAc
  3. washThe organic layers were washed once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product (43 mg) was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-a8db8ff26ba5484c8bbac8967148b21e
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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