Sodium Hydroxide → 1-[6-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)naphthalen-2-yl]cyclopent-3-ene carboxylic acid

HRID 481408Notes

Reaction equation

HRID 481408 reaction equation
C([O:3][C:4]([C:6]1([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[C:26]5=[N:27][C:28]([CH3:32])=[CH:29][C:30]([CH3:31])=[C:25]5[N:24]=[C:23]4[CH2:33][CH3:34])[CH:17]=3)[CH:12]=2)[CH2:10][CH:9]=[CH:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH2:33]([C:23]1[N:22]([CH2:21][C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[CH:12]=[C:11]([C:6]2([C:4]([OH:5])=[O:3])[CH2:10][CH:9]=[CH:8][CH2:7]2)[CH:20]=[CH:19]3)[C:26]2=[N:27][C:28]([CH3:32])=[CH:29][C:30]([CH3:31])=[C:25]2[N:24]=1)[CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 676668611-[6-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)naphthalen-2-yl]cyclopent-3-ene carboxylic acid ethyl ester2×

Product 1

HCID 190662511-[6-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)naphthalen-2-yl]cyclopent-3-ene carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Step 4, above (53) (35mg), 2N NaOH (0.5 ml) and 2 ml of ethanol was heated at 80° C. for 20 hours. The reaction mixture was cooled to ambient temperature and the solvent was evaporated. The residue was dissolved in water and extracted (1×5 ml EtOAc). The aqueous solution was then neutralized with concentrated acetic acid and extracted (2×5 ml CHCl3). The combined organics were dried over MgSO4, filtered and concentrated to dryness. The residue was azeotroped with heptane to remove trace amounts of acetic acid. The crude material was diluted with EtOAc and hexanes were added to crash out the product, which was filtered and dried to yield the title compound (54).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted (1×5 ml EtOAc)
  4. extractionextracted (2×5 ml CHCl3)
  5. dry with materialThe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was azeotroped with heptane
  9. customto remove trace amounts of acetic acid
  10. additionThe crude material was diluted with EtOAc and hexanes
  11. additionwere added
  12. filtrationwas filtered
  13. customdried

Sources & evidence

ORD record
ord-a68c23ca8c1842dcb3cb32dca97a16f6
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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