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

HRID 1628110Notes

Reaction equation

[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][N:16](S(C5C=CC(C)=CC=5)(=O)=O)[C:13]=4[N:14]=[CH:15][C:10]3=[C:9](/[CH:29]=[CH:30]/[C:31]([O:33]CC)=[O:32])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCOCC1>[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][NH:16][C:13]=4[N:14]=[CH:15][C:10]3=[C:9](/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 65 °C

Procedure

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.

Workup

temperaturethe mixture was cooled to rt
concentrationThe mixture was partially concentrated in vacuo
filtrationthe precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-bca9af613005424aa0614ccdd8ae2962
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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