Hydrochloric Acid → (R)-1-(piperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride
Reaction equation
[C:1]1([C@@H:13]2[CH2:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)[N:5]2[C:6]3[CH:12]=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[CH:3][N:2]=1.O1CCOCC1.[ClH:32]>CCOCC>[ClH:32].[NH:15]1[CH2:16][CH2:17][CH2:18][C@@H:13]([C:1]2[N:5]3[C:6]4[CH:12]=[CH:11][NH:10][C:7]=4[N:8]=[CH:9][C:4]3=[CH:3][N:2]=2)[CH2:14]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A round bottom flask was charged with (R)-tert-butyl 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidine-1-carboxylate (2.8 g, 8.20 mmol), 1,4-dioxane (24 mL) and HCl (4 N in 1,4-dioxane, 6.2 mL, 24.6 mmol). The reaction mixture was heated at about 60° C. for about 18 h. The reaction mixture was cooled to ambient temperature and Et2O (40 mL) was added and the mixture was stirred for about 15 min. The solid was collected by vacuum filtration, while washed with Et2O (50 mL), and then dried in a vacuum oven at about 60° C. to afford (R)-1-(piperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (2.4 g, 94%) as an off-white solid: LC/MS (Table 1, Method b) Rt=0.81 min; MS m/z 242 (M+H)+.
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- filtrationThe solid was collected by vacuum filtration
- washwhile washed with Et2O (50 mL)
- customdried in a vacuum oven at about 60° C.
Sources & evidence
- ORD record
- ord-c8cc20e90bd04420a3c756665484c679
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426411B2
Reaction notes
Loading…