Nitric Acid → N-(4-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyrazine-2-carboxamide

HRID 13423Notes

Reaction equation

HRID 13423 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([N:8]1[C@@H:12]([CH3:13])[CH2:11][CH2:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH:28]=[N:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:16][C:15]=1[F:29])(=[O:7])[CH3:6]>C(Cl)(Cl)Cl>[C:5]([N:8]1[C@@H:12]([CH3:13])[CH2:11][CH2:10][C@@H:9]1[C:14]1[C:15]([F:29])=[CH:16][C:17]([NH:20][C:21]([C:23]2[CH:28]=[N:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[C:18]([N+:1]([O-:4])=[O:2])[CH:19]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 67482899N-(4-((5S)-1-acetyl-5-methylpyrrolidin-2-yl)-3-fluorophenyl)pyrazine-2-carboxamide

Product 1

HCID 67482980N-(4-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyrazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1 ml of fuming nitric acid was added to 59 mg of N-(4-((5S)-1-acetyl-5-methylpyrrolidin-2-yl)-3-fluorophenyl)pyrazine-2-carboxamide at room temperature, and the reaction liquid was stirred at the same temperature for 30 minutes. The reaction liquid was diluted with chloroform, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduce pressure, and purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate) to obtain the entitled compound as a pale yellow oily substance. (Rf: trans form>cis form.)

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with aqueous saturated sodium bicarbonate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away
  6. custompurified
  7. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate)
  8. customto obtain the entitled compound as a pale yellow oily substance
  9. custom(Rf: trans form>cis form.)

Sources & evidence

ORD record
ord-b1646f6a829743f383e61eefbf09f40b
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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