Pyridine → N-[4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-2-trifluoromethoxyphenyl]acetamide

HRID 722221Notes

Reaction equation

HRID 722221 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([O:15][C:16]([F:19])([F:18])[F:17])[CH:6]=1)=[NH:4].CN1CCC[C:22]1=[O:26].N1C=CC=CC=1.ClC(OCC)=O>O>[O:26]=[C:22]1[O:1][N:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([O:15][C:16]([F:18])([F:17])[F:19])[CH:6]=2)[NH:4]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 13387N-methyl-2-pyrrolidoneHCID 178474202N-[4-[(E)-N'-hydroxycarbamimidoyl]-2-(trifluoromethoxy)phenyl]acetamide

Product 1

HCID 135839374N-[4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-2-trifluoromethoxyphenyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The mixture consisting of 130 mg of N-[4-(N-hydroxycarbamimidoyl)-2-trifluoromethoxyphenyl]acetamide, 2 ml of N-methylpyrrolidone, 0.55 ml of pyridine and 0.049 ml of ethyl chloroformate was stirred at 80° C. for 5 hours. After cooling, the mixture was diluted with water and the product was extracted with 20 ml of ethyl acetate. The organic phase was dried over sodium sulfate and evaporated at 40° C. under reduced pressure.

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with 20 ml of ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-8bacab7f953c47d2bcdb12309272f8b9
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Reaction notes

Loading…