5-(4-Methylpiperazin-1-yl)pyridin-2-amine → 1-Isobutyl-4-(6-nitro-3-pyridyl)piperazine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14]C(N3CCCCC3)[CH2:12][CH2:11]2)=[CH:6][N:5]=1)([O-:3])=[O:2].[CH2:22]([N:26]1CCN(C2C=CC(N)=NC=2)CC1)[CH:23]([CH3:25])[CH3:24].CN1CCN(C2C=CC(N)=NC=2)CC1>>[CH2:22]([N:26]1[CH2:12][CH2:11][N:10]([C:7]2[CH:6]=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:15][CH2:14]1)[CH:23]([CH3:25])[CH3:24]Participants
4
Procedure
1-isobutyl-4-(6-nitro-3-pyridyl)piperazine was synthesized in a manner similar to that used in the synthesis of 2-nitro-5-[4-(1-piperidyl)-1-piperidyl]pyridine which was then converted 5-(4-isobutylpiperazin-1-yl)pyridin-2-amine in a manner similar to that used in the synthesis of 5-(4-methylpiperazin-1-yl)pyridin-2-amine 1H NMR (600 MHz, CHLOROFORM-d) δ ppm 0.88 (d, J=6.73 Hz, 6H) 1.71-1.84 (m, 1H) 2.10 (d, J=7.32 Hz, 2H) 2.46-2.58 (m, 4H) 2.97-3.07 (m, 4H) 4.12 (s, 2H) 6.45 (d, J=8.78 Hz, 1H) 7.14 (dd, J=8.78, 2.93 Hz, 1H) 7.75 (d, J=2.93 Hz, 1H). LCMS (ESI) 235 (M+H).
Sources & evidence
- ORD record
- ord-e0bb68ca007b41d9b67c9f9df9fd0231
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598197B2
Reaction notes
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