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

Temperatur

65 °C

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 NaOH (2 N aqueous, 1.30 mL, 2.60 mmol). The reaction mixture was heated to about 65° C. After about 15 h, the reaction mixture was cooled to ambient temperature and the pH of the reaction mixture was adjusted to about pH 1 with concentrated HCl. The mixture was partially concd in vacuo to remove the 1,4-dioxane and the resulting yellow solid 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, 37.2%): LC/MS (Table 1, Method a) Rt=1.85 min; MS m/z: 311 (M+H)+.

1. temperaturethe reaction mixture was cooled to ambient temperature
2. customto remove the 1,4-dioxane
3. filtrationthe resulting yellow solid was collected by filtration
4. customdried in vacuo

ORD-Eintrag

ord-49e24f18893e45e19c8203853da6d176

Quelldatensatz

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08426411B2