HCID 67165879, compound → HCID 136365796, compound

HRID 878843Notes

Reaction equation

HRID 878843 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]([C:14]2[CH2:18][C:17]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)([C:19]([F:22])([F:21])[F:20])[O:16][N:15]=2)[CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8])(=[O:3])[CH3:2]>COC(OC)N(C)C>[C:1]([NH:4][C:5]1[CH:13]=[C:12]([C:14]2[CH2:18][C:17]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)([C:19]([F:22])([F:20])[F:21])[O:16][N:15]=2)[CH:11]=[CH:10][C:6]=1[C:7]([NH:9][CH:14]=[N:15][O:16][CH3:17])=[O:8])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 67165879HCID 67165879, compound

Product 1

HCID 136365796HCID 136365796, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A mixture of 0.21 g of 2-acetylamino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide and 10 mL of N,N-dimethylformamide dimethylacetal was stirred at room temperature for 1.5 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was dissolved in 3 mL of 1,4-dioxane, a solution of 0.025 g of methoxyamine hydrochloride in 3 mL of water was added dropwise. After the completion of the addition dropwise, it was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, 5 mL of water was added in the residue, and extracted with ethyl acetate (10 mL×1). The organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that were eluated with ethyl acetate-hexane (1:2) to obtain 0.07 g of the aimed product as colorless resinous substance.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in 3 mL of 1,4-dioxane
  4. additiona solution of 0.025 g of methoxyamine hydrochloride in 3 mL of water was added dropwise
  5. additionAfter the completion of the addition dropwise
  6. stirringto stir at room temperature further for 30 minutes
  7. customAfter the completion of the reaction
  8. distillationthe solvent was distilled off under reduced pressure, 5 mL of water
  9. additionwas added in the residue
  10. extractionextracted with ethyl acetate (10 mL×1)
  11. dry with materialdried over saturated sodium chloride aqueous solution
  12. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  13. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-cd46d34c461e422080fa02ec0112e5d3
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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