Potassium Hydroxide → HCID 86691855, compound

HRID 1616238Notes

Reaction equation

HRID 1616238 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:16]([O:18]C)=[O:17])=[CH:10][CH:11]=2)[N:6]([CH3:24])[C:5]1=[O:25].[OH-].[K+]>C1COCC1.CO>[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:16]([OH:18])=[O:17])=[CH:10][CH:11]=2)[N:6]([CH3:24])[C:5]1=[O:25]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86691854HCID 86691854, compound

Product 1

HCID 86691855HCID 86691855, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-methylbenzoate (15-4) (550 mg, 1.5 mmol, 1.0 eq.) was dissolved in THF (2.5 mL)/MeOH (2.5 mL) and potassium hydroxide (340 mg, 6.0 mmol, 4.0 eq.) was added. The mixture stirred overnight at ambient temperature. Upon completion, the reaction mixture was concentrated and 1N HCl was added. The mixture was then extracted with ethyl acetate and the combined organics were dried over magnesium sulfate, filtered and concentrated to afford 3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-methylbenzoic acid (55-1) as a white solid. MS (M+H)+: observed=354.0, calculated=354.2.

Workup

  1. additionwas added
  2. concentrationUpon completion, the reaction mixture was concentrated
  3. addition1N HCl was added
  4. extractionThe mixture was then extracted with ethyl acetate
  5. dry with materialthe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6c7f52a4495646b7b1fce45730b45529
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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