Hydrochloric Acid → HCID 58180624, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylthiazole-5-carboxylate (example 71A, 103 mg, 0.203 mmol) in MeOH (2 mL) was added NaOH (1.420 mL, 1.420 mmol). The solution was then stirred at 65° C. for 18 hrs. The reaction mixture was then cooled to room temperature and concentrated in vacuo to afford yellow slurry. The mixture was then diluted with water, brought to pH 4 with 1N HCl, and the precipitate collected by vacuum filtration. The filtrate was then extracted with CH2Cl2; the organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude residue was then purified by silica-gel flash chromatography using an Isco 40 g column eluting from 0-8% MeOH/CH2Cl2. Desired fractions were combined with the collected precipitate and concentrated to afford 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylthiazole-5-carboxylic acid (126 mg, 126% yield) as an orange/yellow solid.

Provenance & Evidence