HCID 68870456, compound → HCID 53358426, compound

HRID 1817885Notes

Reaction equation

HRID 1817885 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([NH:19][CH2:20][CH2:21][O:22][C:23]([F:26])([F:25])[F:24])=[C:10]([NH:12][C:13](=O)[C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=1)(=[O:5])=[O:4])[CH3:2]>C(O)C.[OH-].[Na+]>[C:14]([C:13]1[N:19]([CH2:20][CH2:21][O:22][C:23]([F:26])([F:25])[F:24])[C:9]2[CH:8]=[CH:7][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:11][C:10]=2[N:12]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 1

HCID 68870456HCID 68870456, compound

Product 1

HCID 53358426HCID 53358426, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

N-(5-(Ethylsulfonyl)-2-{[2-(trifluoromethoxy)ethyl]amino}phenyl)-2,2-dimethylpropanamide (187 mg, 0.47 mmol, step A) was dissolved in ethanol and 2N sodium hydroxide solution. The mixture was microwaved for 30 min at 140° C. The reaction mixture was quenched with water and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by PTLC (hexane:acetone=3:1 as eluent) to afford the title compound (60 mg, 34%) as a yellow oil.

Workup

  1. customThe mixture was microwaved for 30 min at 140° C
  2. customThe reaction mixture was quenched with water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customThe residue was purified by PTLC (hexane:acetone=3:1 as eluent)

Sources & evidence

ORD record
ord-b395359352a94e508cda67303e3121e2
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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