Methane → 2-(5-methyl-2-thienyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

HRID 1709580Notes

Reaction equation

HRID 1709580 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14]([C:16]2[S:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=O)=[CH:11][CH:10]=[CH:9][N:8]=1)C.O.[OH-].[K+].C>C(O)CO.CO>[CH3:21][C:18]1[S:17][C:16]([C:14]2[N:6]([CH2:5][C:4]([OH:3])=[O:22])[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:12]3[N:13]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 962WaterHCID 14797Potassium HydroxideHCID 15617199N-[3-[(5-Methyl-2-thienylcarbonyl)amino]-2-pyridinyl]glycine ethyl ester

Product 1

HCID 156171962-(5-methyl-2-thienyl)-3H-imidazo[4,5-b]pyridine-3-acetic acidYield 0.8%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Procedure

A suspension of N-[3-[(5-methyl-2-thienylcarbonyl)amino]-2-pyridinyl]glycine ethyl ester (93.8 g, 0.293 mole) was refluxed in ethylene glycol (500 ml) for 45 minutes. The solution was cooled and water (200 ml) and solid potassium hydroxide pellets (23.25 g, 0.41 mole) were added. The resulting solution was refluxed for one hour and then filtered hot into ice water (2 liters) and acidified with 3N hydrochloric acid to give a solid which was collected by filtration and dried to give 52.3 g of crude title compound (65% yield). A 2.0-g portion was dissolved in hot methanol, treated with charcoal, filtered while hot, and cooled to room temperature. Addition of water caused a precipitate to form which was collected by filtration and dried under high vacuum at room temperature overnight to give 0.68 g of title compound, mp >250° C.

Workup

  1. temperatureThe solution was cooled
  2. temperatureThe resulting solution was refluxed for one hour
  3. filtrationfiltered hot into ice water (2 liters)
  4. customto give a solid which
  5. filtrationwas collected by filtration
  6. customdried
  7. customto give 52.3 g of crude title compound (65% yield)
  8. filtrationfiltered while hot, and
  9. additionAddition of water
  10. customto form which
  11. filtrationwas collected by filtration
  12. customdried under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-73754b128d1d483c9b10bf4e87e06664
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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