N,N-Dimethylglycine → HCID 50997635, compound

HRID 1807378Notes

Reaction equation

HRID 1807378 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O.I[C:23]1[CH:24]=[C:25]([CH:29]([N:31]([O:43][CH3:44])[C:32]([C:34]2[C:35]([CH:40]([F:42])[F:41])=[N:36][N:37]([CH3:39])[CH:38]=2)=[O:33])[CH3:30])[CH:26]=[CH:27][CH:28]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:23]2[CH:24]=[C:25]([CH:29]([N:31]([O:43][CH3:44])[C:32]([C:34]3[C:35]([CH:40]([F:41])[F:42])=[N:36][N:37]([CH3:39])[CH:38]=3)=[O:33])[CH3:30])[CH:26]=[CH:27][CH:28]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 50997446HCID 50997446, compound

Product 1

HCID 50997635HCID 50997635, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chlorophenol (0.2 g, 0.86 mmol) in DMF (2 ml), cesium carbonate (0.7 g, 1.14 mmol), N,N-dimethylglycine (0.01 g, 0.057 mmol), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-(3-iodo-phenyl)-ethyl]methoxy-amide (0.25 g, 0.57 mmol), prepared as described in example P2, and Cul (0.09 g, 0.024 mmol) was subjected to microwave irradiation at 90° C. for 20 minutes. Reaction mass was diluted with water and extracted with ethyl acetate (3×60 ml), washed with water, brine and dried over anhydrous sodium sulfate. The crude mass was purified by chromatography to yield 0.057 g (28% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid {1-[3-(4-chloro-phenoxy)-phenyl]-ethyl}-methoxy-amide in form of a resin.

Workup

  1. customprepared
  2. customirradiation at 90° C. for 20 minutes
  3. customReaction mass
  4. extractionextracted with ethyl acetate (3×60 ml)
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe crude mass was purified by chromatography

Sources & evidence

ORD record
ord-3dab6e6aa2034a7ab7fcca75552bdca7
Source dataset
uspto-grants-2013_01
Patent number
US08357634B2

Reaction notes

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