Water → HCID 131736889, compound

HRID 56001Notes

Reaction equation

HRID 56001 reaction equation
[Cl:1][C:2]1[C:3]([C:12](=O)[CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[CH2:27]([O:29][NH2:30])[CH3:28].O>C(O)C>[Cl:1][C:2]1[C:3]([C:12](=[N:30][O:29][CH2:27][CH3:28])[CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 76850O-ethylhydroxylamine hydrochlorideHCID 66798033N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimide

Product 1

HCID 131736889HCID 131736889, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 214 mg of the N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimide prepared in Step 2 in Synthetic Example 6 in 3 ml of ethanol, 84 mg of ethoxyamine hydrochloride was added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 5 ml of water and extracted with ethyl acetate (5 ml×3), and the resulting organic layers were combined, dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.) using ethyl acetate-hexane (with a gradient of from 2:18 to 5:15) as the eluent to obtain 111 mg of the desired product as a brown resinous substance.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (5 ml×3)
  3. dry with materialdried over saturated aqueous sodium chloride
  4. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.)

Sources & evidence

ORD record
ord-8755dbe0587240c2b5d5541788dc9ab3
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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