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

HRID 2351760Notes

Reaction equation

HRID 2351760 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(O)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

5

Reactant 3

HCID 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 65.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

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 9200 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 gibe 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

Sources & evidence

ORD record
ord-cdf1271be995428d9e80c10daacc6f41
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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