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

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Reaction Steps

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).

Provenance & Evidence