Hydrochloric Acid → 2-(7-(Dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-5-methylthiazole-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

1N Aqueous NaOH (0.962 mL, 0.962 mmol) was added to a suspension of methyl 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-5-methylthiazole-4-carboxylate (example 41, 0.19 g, 0.385 mmol) in ethanol (2 mL) and the mixture was heated at 60° C. for 2 h. The reaction was cooled to room temperature and acidified with 1N HCl to pH 4. The reaction mixture was concentrated and the residue triturated 5× with methanol. The combined methanol washes were concentrated, and the remaining solid washed 3× with 2:1 ether/dichloromethane provided 2-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-5-methylthiazole-4-carboxylic acid (105 mg, 57% yield).

Provenance & Evidence