Water → 4-fluorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

HRID 2072943Notes

Reaction equation

HRID 2072943 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)C.O.[OH-].[K+]>C(O)CO.CO>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[N:6]([CH2:5][C:4]([OH:3])=[O:23])[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:12]3[N:13]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 15617200HCID 15617200, compound

Product 1

HCID 156171894-fluorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acidYield 3.3%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Procedure

A solution of N-[3-[(4-fluorobenzoyl)amino]-2-pyridinyl] glycine ethyl ester (70.0 g, 0.2205 mole) in ethylene glycol was refluxed for 2 hours, cooled and 14% of the solution was removed. To the remaining solution (0.19 mole) was added 88 ml of water and solid potassium hydroxide pellets (21.4 g, 0.38 mole). The solution was heated at reflux for an additional 11/4 hours, filtered into ice water (2 liter) and acidified with 3N hydrochloric acid. The resulting solid was collected by filtration, washed with water and dried under high vacuum at 60° C. overnight to give 45.5 g of crude title compound (88% yield). A 3.5-g portion of the solid was dissolved in hot methanol and filtered while hot, and water was added to the cloud point. Upon cooling to room temperature, solid precipitated which was collected and recrystallized again from methanol/water to give 2.00 g of title compound after drying under high vacuum at 50° C., mp >250° C.

Workup

  1. temperaturecooled
  2. custom14% of the solution was removed
  3. temperatureThe solution was heated
  4. temperatureat reflux for an additional 11/4 hours
  5. filtrationfiltered into ice water (2 liter)
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water
  8. customdried under high vacuum at 60° C. overnight
  9. customto give 45.5 g of crude title compound (88% yield)
  10. filtrationfiltered while hot, and water
  11. additionwas added to the cloud point
  12. customsolid precipitated which
  13. customwas collected
  14. customrecrystallized again from methanol/water

Sources & evidence

ORD record
ord-437c8179a6984fc5a3f5869cf695848c
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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