Hydrochloric Acid → HCID 67068354, compound
Reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([C:20]([O:22]C)=[O:21])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[ClH:24]>O1CCOCC1>[ClH:24].[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of methyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxylate (2.5 g, 7.5 mmol) in 1,4-dioxane (50 mL) was added aqueous 6 N HCl (50.0 mL, 1650 mmol) and the reaction mixture was stirred at about 65° C. for about 5 h and at room temperature for about 72 h. The mixture was re-heated to about 60° C. for about 3 h, and stirred at room temperature for about 48 h. The mixture was re-heated to about 65° C. for about 2 h and then cooled to room temperature. An insoluble bright yellow residue was removed by filtration and the organic solvent was removed under reduced pressure to give a precipitate that was collected and dried to give 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxylic acid hydrochloride (1.92 g, 72%) as a tan solid: LC/MS (Table 2, Method a) Rt=1.48 min; MS m/z: 352 (M−H)−.
Workup
- temperatureThe mixture was re-heated to about 60° C. for about 3 h
- stirringstirred at room temperature for about 48 h
- temperatureThe mixture was re-heated to about 65° C. for about 2 h
- temperaturecooled to room temperature
- customAn insoluble bright yellow residue was removed by filtration
- customthe organic solvent was removed under reduced pressure
- customto give a precipitate that
- customwas collected
- customdried
Sources & evidence
- ORD record
- ord-6c09c974030349f2a1290fcd1e45657a
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365579B2
Reaction notes
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