Diethyl Ether → alpha-(methoxyimino)-N,2-dimethyl-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetamide

HRID 70253Notes

Reaction equation

HRID 70253 reaction equation
C[C:2]1[C:3]([CH3:30])=[C:4]([C:23](=[N:27][O:28][CH3:29])[C:24]([NH2:26])=[O:25])[CH:5]=[C:6]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[N:9]=2)[CH:7]=1.CN.[CH2:33](OCC)C>O1CCCC1>[CH3:29][O:28][N:27]=[C:23]([C:4]1[CH:5]=[C:6]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[N:9]=2)[CH:7]=[CH:2][C:3]=1[CH3:30])[C:24]([NH:26][CH3:33])=[O:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6329MethylamineHCID 86641520methyl alpha-(methoxyimino)-2-methyl-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetamide

Product 1

HCID 86641519alpha-(methoxyimino)-N,2-dimethyl-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl α-(methoxyimino)-2-methyl-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetamide (i.e. the product of Example 13) (0.062 g, 0.149 mmol) in tetrahydrofuran (2 mL) under a nitrogen atmosphere was added methylamine (33% by weight in ethanol). The reaction mixture was stirred overnight at room temperature and then concentrated under reduced pressure to leave a solid. Hexanes and diethyl ether were added to the solid, and the mixture was filtered to obtain the tile compound, a compound of the present invention, as a white solid (56 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto leave a solid
  3. filtrationthe mixture was filtered
  4. customto obtain the tile compound

Sources & evidence

ORD record
ord-06d94a5202bb4f13b6e567db876c9943
Source dataset
uspto-grants-2014_09
Patent number
US08822521B2

Reaction notes

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