m-Chloroperbenzoic acid → HCID 86587018, compound

HRID 723820Notes

Reaction equation

HRID 723820 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:8])=[CH:5][N:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:25]>ClCCl.CO.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:19])[C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH+:9]([O-:25])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 218782696-(Dimethylamino)-N-(4-fluorophenyl)-3-pyridinecarboxamide

Product 1

HCID 86587018HCID 86587018, compoundYield 13.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 6-dimethylamino-N-(4-fluoro-phenyl)-nicotinamide (0.027 g, 0.11 mmol, prepared as in Example 1) in 2 mL of dry dichloromethane/methanol (4:1) was added 3-chloroperoxybenzoic acid (0.020 g, 0.12 mmol) at 0° C. The reaction mixture was then heated to reflux and additional 3-chloroperoxybenzoic acid (0.040 g, 0.24 mmol) was added. After heating for a total of 7 h the reaction mixture was cooled, diluted with chloroform and washed with aqueous sodium carbonate (1M), dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography, using 10% methanol/dichloromethane saturated with ammonia, yielded 4 mg (13%) of the desired product as a white solid. MS (EI) m/z 274.18 (M−H)−.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. temperatureAfter heating for a total of 7 h the reaction mixture
  4. temperaturewas cooled
  5. washwashed with aqueous sodium carbonate (1M)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-6932adbf90014cdaa9c3766a2be7311c
Source dataset
uspto-grants-2006_11
Patent number
US07141590B2

Reaction notes

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