Lithium Hydroxide → 3-{[2-(4-Amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}benzoic acid

HRID 1986371Notes

Reaction equation

HRID 1986371 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:9]3[CH:14]=[C:13]([O:15][C:16]4[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=4)[C:19]([O:21]C)=[O:20])[N:12]=[CH:11][C:10]=3[N:26]=2)=[N:4][O:5][N:6]=1.[OH-].[Li+]>C1COCC1.O>[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:9]3[CH:14]=[C:13]([O:15][C:16]4[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=4)[C:19]([OH:21])=[O:20])[N:12]=[CH:11][C:10]=3[N:26]=2)=[N:4][O:5][N:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11304916Methyl 3-{[2-(4-amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}benzoate

Product 1

HCID 113159523-{[2-(4-Amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}benzoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

The product from Step 8 (0.22 g, 0.514 mmol) in THF (10 mL) was treated with a solution of 1N lithium hydroxide in water (1.5 mL) and heated to 65° C. for 10 h. The reaction mixture was cooled and concentrated and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the organic layers were combined, washed with brine and dried over Na2SO4 and concentrated to give the title compound (0.20 g, 94%). MS (ES+) m/e 415 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c6c201431ada46059c324e8abe00b9b7
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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