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, Et2O (40 mL) was added and the mixture was stirred for about 15 min. The solid was collected by vacuum filtration and washed with Et2O (50 mL) 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 as an off-white solid (2.4 g, 94%): 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
- washwashed with Et2O (50 mL)
- customthen dried in a vacuum oven at about 60° C.
Sources & evidence
- ORD record
- ord-decb9f5107334f32a4a2c8c5c0166f15
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426411B2
Reaction notes
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