Sodium Azide → HCID 59519478, compound

HRID 1161824Notes

Reaction equation

HRID 1161824 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:6]([F:22])[C:5]=1Cl)(=[O:3])[CH3:2].[N-:24]=[N+]=[N-].[Na+]>CC(C)=O.O>[F:22][C:6]1[C:5]2[C:4](=[C:1]([CH3:2])[O:3][N:24]=2)[N:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[C:7]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 66999313HCID 66999313, compound

Product 1

HCID 59519478HCID 59519478, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 6-acetyl-5-chloro-4-fluoro-3-(2-fluorophenylamino)picolinate (WO 2005/051906) (2 g, 5 mmole) in a mixture of acetone (36 ml) and H2O (12 ml) is added NaN3 (487 mg, 7.5 mmol). The reaction is heated at 65° C. for 16 h and cooled to room temperature. Acetone is concentrated and the resulting mixture is extracted with EtOAc (2×50 ml). The combined organic solution is washed with brine (50 ml), dried over MgSO4 and concentrated to give a yellow solid. To the solid is added H2O (24 ml) and the reaction is heated at reflux for 3 h. The reaction is cooled to room temperature, filtered, and washed with H2O. The resulting solid is dried under high vacuum with P2O5 at 65° C. for 24 h to give the title compound.

Workup

  1. temperaturecooled to room temperature
  2. concentrationAcetone is concentrated
  3. extractionthe resulting mixture is extracted with EtOAc (2×50 ml)
  4. washThe combined organic solution is washed with brine (50 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. temperaturethe reaction is heated
  9. temperatureat reflux for 3 h
  10. temperatureThe reaction is cooled to room temperature
  11. filtrationfiltered
  12. washwashed with H2O
  13. dry with materialThe resulting solid is dried under high vacuum with P2O5 at 65° C. for 24 h

Sources & evidence

ORD record
ord-271154312aea4d60b5b31ba8db556623
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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