Trifluoroacetic acid → N-(4-benzyloxy-5-fluoro-2-nitrophenyl)pyrazinecarboxamide

HRID 13325Notes

Reaction equation

HRID 13325 reaction equation
FC(F)(F)C(O)=O.[N+:8]([O-:11])([O-])=[O:9].[K+].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]2[CH:35]=[N:34][CH:33]=[CH:32][N:31]=2)=[O:29])=[CH:23][C:22]=1[F:36])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)(Cl)Cl>[CH2:13]([O:20][C:21]1[C:22]([F:36])=[CH:23][C:24]([NH:27][C:28]([C:30]2[CH:35]=[N:34][CH:33]=[CH:32][N:31]=2)=[O:29])=[C:25]([N+:8]([O-:11])=[O:9])[CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24434Potassium NitrateHCID 23145734N-(4-benzyloxy-3-fluorophenyl)pyrazinecarboxamide

Product 1

HCID 23145743N-(4-benzyloxy-5-fluoro-2-nitrophenyl)pyrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

40 ml of trifluoroacetic acid and 1.99 g of potassium nitrate were added to a chloroform (40 ml) suspension of 5.80 g of N-(4-benzyloxy-3-fluorophenyl)pyrazinecarboxamide, with cooling with ice, and the reaction liquid was stirred overnight at room temperature. The solvent was evaporated away under reduced pressure, and aqueous saturated sodium bicarbonate was added to it. The resulting solid was washed with a mixed solvent of ethyl acetate and hexane to obtain the entitled compound as a yellow solid.

Workup

  1. temperaturewith cooling with ice
  2. customthe reaction liquid
  3. customThe solvent was evaporated away under reduced pressure, and aqueous saturated sodium bicarbonate
  4. additionwas added to it
  5. washThe resulting solid was washed with a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ca3065c4765142768db3178da2f15c3d
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

Loading…