N-bromobutanimide → 5-(5-Amino-6-bromopyrazin-2-yl)piperidin-2-one
Reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C1C(=O)N([Br:22])C(=O)C1>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[N:6][C:7]=1[Br:22]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
To 5-(5-aminopyrazin-2-yl)piperidin-2-one (25 mg, 0.13 mmol) acetonitrile (10 mL) solution at 0° C. was added NBS (23.2 mg, 0.13 mmol) and the reaction mixture was stirred at 0° C. for 30 min, then at room temperature for 4 h. The reaction mixture was concentrated, and the residue was basified by 1 N NaOH (140 ul), diluted with methanol (2 mL), concentrated. The residue was triturated with EtOAc (3×1 mL), and the EtOAc supernatants were collected, combined and concentrated and a light solid was obtained as crude 5-(5-amino-6-bromopyrazin-2-yl)piperidin-2-one which was used in next step without further purification. LCMS (m/z): 241/243 (MH+), 0.41 min.
Workup
- waitat room temperature for 4 h
- concentrationThe reaction mixture was concentrated
- additiondiluted with methanol (2 mL)
- concentrationconcentrated
- customThe residue was triturated with EtOAc (3×1 mL)
- customthe EtOAc supernatants were collected
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-003c63f7b1924d64b9fdf63881a75a68
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242996B2
Reaction notes
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