Hydrochloric Acid → (E)-3-(1-cyclohexyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)acrylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-ethyl 3-(1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)acrylate (0.064 g, 0.13 mmol) in 1,4-dioxane (5 mL) was added aqueous NaOH (2 N, 1.30 mL, 2.60 mmol). The mixture was heated to about 65° C. After about 15 h, the mixture was cooled to rt and the pH of the reaction mixture was adjusted to about pH=1 with concentrated HCl. The mixture was partially concentrated in vacuo and the precipitate was collected by filtration and dried in vacuo to provide (E)-3-(1-cyclohexyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)acrylic acid (0.015 g, 37%): LC/MS (Table 2, Method a) Rt=1.85 min; MS m/z: 311 (M+H)+. Syk IC50=B.

Provenance & Evidence