5-(4-Methylpiperazin-1-yl)pyridin-2-amine → 1-Isopropyl-4-(6-nitropyridin-3-yl)piperazine

HRID 2362280Notes

Reaction equation

HRID 2362280 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].[CH:22]([N:25]1CCN(C2C=CC(N)=NC=2)CC1)([CH3:24])[CH3:23].CN1CCN(C2C=CC(N)=NC=2)CC1>>[CH:22]([N:25]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)([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 223298335-(4-Methylpiperazin-1-yl)pyridin-2-amineHCID 434619445-(4-(Propan-2-yl)piperazin-1-yl)pyridin-2-amineHCID 675134152-Nitro-5-[4-(1-piperidyl)-1-piperidyl]pyridine

Product 1

HCID 575020971-Isopropyl-4-(6-nitropyridin-3-yl)piperazine

Procedure

1-isopropyl-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 to 5-(4-isopropylpiperazin-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 1.06 (d, J=6.44 Hz, 6 H) 2.59-2.75 (m, 5 H) 2.97-3.10 (m, 4 H) 4.13 (s, 2 H) 6.45 (d, J=8.78 Hz, 1 H) 7.15 (dd, J=9.08, 2.93 Hz, 1 H) 7.76 (d, J=2.93 Hz, 1 H). LCMS (ESI) 221 (M+H).

Sources & evidence

ORD record
ord-0523de3bd39c4d5396a0d79b377895eb
Source dataset
uspto-grants-2014_04
Patent number
US08691830B2

Reaction notes

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