Nitric Acid → HCID 23145445, compound

HRID 13413Notes

Reaction equation

HRID 13413 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)=[O:21])=[CH:15][C:14]=1[F:28])(=[O:7])[CH3:6].C(=O)(O)[O-].[Na+]>O>[C:5]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[C:14]([F:28])=[CH:15][C:16]([NH:19][C:20]([C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)=[O:21])=[C:17]([N+:1]([O-:4])=[O:2])[CH:18]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 23145506N-(4-(1-acetylpyrrolidin-2-yl)-3-fluorophenyl)pyrazine-2-carboxamide

Product 1

HCID 23145445HCID 23145445, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

40 ml of fuming nitric acid was added to 3.9 g of N-(4-(1-acetylpyrrolidin-2-yl)-3-fluorophenyl)pyrazine-2-carboxamide with cooling with ice, and the reaction liquid was stirred at room temperature for 2 hours. The reaction liquid was diluted with water with ice, made basic with aqueous saturated sodium bicarbonate, and then extracted with chloroform. The organic layer was washed with saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1) to obtain the entitled compound as a yellow oily substance.

Workup

  1. temperaturewith cooling with ice
  2. customthe reaction liquid
  3. customThe reaction liquid
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)
  9. customto obtain the entitled compound as a yellow oily substance

Sources & evidence

ORD record
ord-6123fba2a62d451ea7d84b1851417a2b
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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