Water → N-Ethoxymethyl-N-(3-methyl-5-isoxazolyl)-4-(trifluoromethyl)nicotinamide

HRID 1744263Notes

Reaction equation

HRID 1744263 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8](=[O:19])[C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[N:11][CH:10]=2)[O:4][N:3]=1.[C:20](=[O:23])([O-])[O-].[K+].[K+].Br[CH2:27][C:28]#N.O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[CH2:27]([O:23][CH2:20][N:7]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)[C:8](=[O:19])[C:9]1[C:14]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:12]=[N:11][CH:10]=1)[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 11369270N-(3-Methyl-5-isoxazolyl)-4-(trifluoromethyl)nicotinamide

Product 1

HCID 12137633N-Ethoxymethyl-N-(3-methyl-5-isoxazolyl)-4-(trifluoromethyl)nicotinamideYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

N-(3-Methyl-5-isoxazolyl)-4-(trifluoromethyl)nicotinamide (Compound No. 1-2, 107.1 mg, 0.39 mmol) prepared according to Example 1 was dissolved in dimethylformamide (2 ml). To this solution, potassium carbonate (81.4 mg, 0.59 mmol) and bromoacetonitrile (30 μl, 0.43 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The resulting residue was purified by thin layer chromatography (a developing solvent: hexane/ethyl acetate=1/1) to obtain the title compound (91.3 mg, yield 75%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by thin layer chromatography (a developing solvent

Sources & evidence

ORD record
ord-cae72c3d8876401a8e989f6d0aaf60f2
Source dataset
uspto-grants-2006_03
Patent number
US07015236B2

Reaction notes

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