Sodium Hydroxide → [4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamino]-phenyl-acetic acid

HRID 1492613Notes

Reaction equation

HRID 1492613 reaction equation
[C:1]([CH:5]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]2[C:24]3=[N:25][C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:23]3[N:22]=[C:21]2[CH2:31][CH3:32])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O:3]C)=[O:2].[OH-].[Na+]>CO>[C:1]([CH:5]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][N:20]2[C:24]3=[N:25][C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:23]3[N:22]=[C:21]2[CH2:31][CH3:32])=[CH:17][CH:18]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10251994HCID 10251994, compound

Product 1

HCID 10409549[4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamino]-phenyl-acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.45 g of the product of Step A dissolved in 5.0 mL methanol, was added 3.0 mL of 3N NaOH solution, and the mixture was stirred for 30 minutes. The methanol was removed in vacuo and the water was removed by azeotropic distillation with toluene. The o toluene was removed in vacuo, then the product was redissolved in CHCl3 and excess NaOH was removed by filtration of the suspension through a celite pad. The filtrate was concentrated to a clear oil and purified on a silica gel flash chromatography column eluted with CHCl3 /MeOH/NH4OH (80:15:1). The product fractions were combined and concentrated. The resultant oil was triturated with ether to yield 396 mg (91%) of the title compound as a white powder.

Workup

  1. customThe methanol was removed in vacuo
  2. customthe water was removed by azeotropic distillation with toluene
  3. customThe o toluene was removed in vacuo
  4. dissolutionthe product was redissolved in CHCl3
  5. customexcess NaOH was removed by filtration of the suspension through a celite pad
  6. concentrationThe filtrate was concentrated to a clear oil
  7. custompurified on a silica gel flash chromatography column
  8. washeluted with CHCl3 /MeOH/NH4OH (80:15:1)
  9. concentrationconcentrated
  10. customThe resultant oil was triturated with ether

Sources & evidence

ORD record
ord-43d59c32ddb84160af0f35148465eedd
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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