HEXAHYDRO-PYRROLO[1,2-A]PYRAZIN-1-ONE → HCID 67355979, compound
Reaction equation
[C:1]1(=[O:10])[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][CH2:8][CH2:9][CH:2]12.Br[C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[N:16][CH:17]=1>>[N+:18]([C:15]1[N:16]=[CH:17][C:12]([N:6]2[CH2:5][CH2:4][N:3]3[CH2:7][CH2:8][CH2:9][CH:2]3[C:1]2=[O:10])=[CH:13][CH:14]=1)([O-:20])=[O:19]Participants
3
Procedure
Following general N—C coupling procedure 1, hexahydro-pyrrolo[1,2-a]pyrazin-1-one (0.202 g, 1.44 mmol), was combined with 5-bromo-2-nitropyridine (0.293 g, 1.44 mmol, 1.0 eq) which gave 2-(6-Nitro-pyridin-3-yl)hexahydro-pyrrolo[1,2-a]pyrazin-1-one as a tan solid (0.170 g, 0.616 mmol) in 43% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.79-2.19 (m, 1H) 2.31 (br. s., 1H) 2.77 (br. s., 1H) 2.98-3.16 (m, 1H) 3.26 (dt, J=12.05, 4.52 Hz, 1H) 3.47 (br. s., 1H) 3.80 (br. s., 1H) 3.95-4.23 (m, 1H) 8.15 (dd, J=8.53, 2.51 Hz, 1H) 8.32 (d, J=8.53 Hz, 1H) 8.70 (d, J=2.51 Hz, 1H). MS m/z 263.1 (M+H)+.
Sources & evidence
- ORD record
- ord-28905cc3024548359ed76f3cab91b094
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957074B2
Reaction notes
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