Nitric Acid → HCID 117957348, compound

HRID 1474435Notes

Reaction equation

HRID 1474435 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[NH:17][C:18](=[O:21])[O:19][CH3:20])=[O:8])[N:4]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[N:3]=1.OS(O)(=O)=O.[N+:34]([O-])([OH:36])=[O:35]>>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([N+:34]([O-:36])=[O:35])=[CH:12][C:11]=2[NH:17][C:18](=[O:21])[O:19][CH3:20])=[O:8])[N:4]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[N:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 117957331HCID 117957331, compound

Product 1

HCID 117957348HCID 117957348, compound

Procedure

Methyl (2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamido)-3-methylphenyl)carbamate prepared in Example 54 (100 mg, 0.22 mmol) was introduced in a V-shaped vial, and the vial was placed in an ice bath. H2SO4 (0.5 mL) was added to the vial at 0° C. and subjected to a reaction until the solid disappeared. After the solid completely disappeared, HNO3 (77 μL, 1.29 mmol, 6.0 eq) was added to the solution dropwise. The vial was removed from the ice bath 10 minutes after the initiation of the reaction, and the reaction mixture was allowed to react at room temperature for 1 hour. Upon completion of the reaction, 15 mL of ice was placed in a 50 mL flask, and the reaction mixture was added thereto. The reaction mixture was washed with water several times and filtered. The residue was extracted with ether and H2O, dried over MgSO4 and concentrated under reduced pressure. Subsequently, the residue was purified by silica gel column chromatography (EA:Hex=1:1) to obtain the title compound in a white solid (95 mg, yield: 85%).

Workup

  1. customthe vial was placed in an ice bath
  2. customsubjected to a reaction until the solid
  3. customThe vial was removed from the ice bath 10 minutes
  4. customafter the initiation of the reaction
  5. customto react at room temperature for 1 hour
  6. customwas placed in a 50 mL flask
  7. additionthe reaction mixture was added
  8. washThe reaction mixture was washed with water several times
  9. filtrationfiltered
  10. extractionThe residue was extracted with ether and H2O
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated under reduced pressure
  13. customSubsequently, the residue was purified by silica gel column chromatography (EA:Hex=1:1)

Sources & evidence

ORD record
ord-6821832bafd341f98ec21dc99935ff88
Source dataset
uspto-grants-2015_04
Patent number
US09018233B2

Reaction notes

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