Hydrochloric Acid → 5-(5-Aminopyrazin-2-yl)piperidin-2-one
Reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[N:9]=[CH:10][C:11]([NH:14]C(=O)OC(C)(C)C)=[N:12][CH:13]=2)[CH2:4][CH2:3]1.Cl>CO>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([CH:5]2[CH2:6][NH:7][C:2](=[O:1])[CH2:3][CH2:4]2)=[N:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of tert-butyl 5-(6-oxopiperidin-3-yl)pyrazin-2-ylcarbamate (60 mg, 0.205 mmol) and conc HCl (1 mL) in methanol (2 mL) was heated with 70° C. oil bath for 1 hour and the reaction mixture was cooled down, concentrated to dryness and the residue was redissolved in methanol (3 mL), and to it was added NaHCO3 (200 mg), and the mixture was heated with 70° C. oil bath for 2 h. The solid suspension of reaction mixture was removed by filtration, and the filtrate was concentrated and a light yellow solid was obtained as crude 5-(5-aminopyrazin-2-yl)piperidin-2-one which was used directly in next step without further purification. LCMS (m/z): 193.1 (MH+), 0.22 min.
Workup
- temperaturethe reaction mixture was cooled down
- concentrationconcentrated to dryness
- dissolutionthe residue was redissolved in methanol (3 mL)
- additionto it was added NaHCO3 (200 mg)
- temperaturethe mixture was heated with 70° C. oil bath for 2 h
- additionThe solid suspension of reaction mixture
- customwas removed by filtration
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-f4680f8d3eeb4bb285654b46fcc35c9e
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242996B2
Reaction notes
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