Potassium Hydroxide → HCID 178507298, compound

HRID 1434889Notes

Reaction equation

HRID 1434889 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([NH:12]C(OCC)=O)[N:9]=[C:8]2[NH:18][CH:19]=[N:20][C:7]=12.[OH-].[K+].[Cl-].[NH4+]>C(O)C>[NH2:12][C:10]1[N:9]=[C:8]2[NH:18][CH:19]=[N:20][C:7]2=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 178473423HCID 178473423, compound

Product 1

HCID 178507298HCID 178507298, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-(2-thienyl)-5-ethoxycarbonylamino-3H-imidazo[4,5-b]pyridine (1.21 g, 3.72 mmol) in ethanol (130 ml), potassium hydroxide (7.29 g) was added and heated under reflux for 4 hours. To this solution, an aqueous ammonium chloride solution (7.65 g/26 ml) was added, followed by evaporation under reduced pressure to remove the solvent. The product was isolated by silica gel column chromatography (methylene chloride:ethanol=9:1 to 7:3) to give 5-amino-7-(2-thienyl)-3H-imidazo[4,5-b]pyridine (870 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customfollowed by evaporation under reduced pressure
  4. customto remove the solvent
  5. customThe product was isolated by silica gel column chromatography (methylene chloride:ethanol=9:1 to 7:3)

Sources & evidence

ORD record
ord-1aad53e274574790b60592a80a807e7e
Source dataset
uspto-grants-2009_11
Patent number
US07615628B2

Reaction notes

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