| Identification | Back Directory | [Name]
1-(6-nitropyridin-3-yl)piperazine | [CAS]
775288-71-6 | [Synonyms]
AKOS BBV-002250
OTAVA-BB 1314167
1-(6-Nitro-3-pyridyl)piperazine
1-(6-Nitro-3-pyridinyl)piperazine
1-(6-nitropyridin-3-yl)piperazine
Piperazine, 1-(6-nitro-3-pyridinyl)- | [Molecular Formula]
C9H12N4O2 | [MDL Number]
MFCD09041112 | [MOL File]
775288-71-6.mol | [Molecular Weight]
208.22 |
| Chemical Properties | Back Directory | [Boiling point ]
422.8±40.0 °C(Predicted) | [density ]
1.278±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Chloroform; Methanol | [form ]
Solid | [pka]
8.50±0.10(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C9H12N4O2/c14-13(15)9-2-1-8(7-11-9)12-5-3-10-4-6-12/h1-2,7,10H,3-6H2 | [InChIKey]
UBCDLQPOKISIDX-UHFFFAOYSA-N | [SMILES]
N1(C2=CC=C([N+]([O-])=O)N=C2)CCNCC1 |
| Hazard Information | Back Directory | [Uses]
1-?(6-?Nitro-?3-?pyridinyl)?piperazine is a reagent used in the preparation of highly potent and orally bioavailable 4-Thiazol-N-(pyridin-2-yl)pyrimidin-2-amine cyclin-dependant kinases as anticancer agents. Also is an impurity of Palbociclib (P139900), an experimental drug for the treatment of breast cancer being developed by Pfizer. It is a selective inhibitor of the cyclin-dependent kinases CDK4 and CDK6. | [Synthesis]
GENERAL METHODS: A mixture of 5-bromo-2-nitropyridine (24.7 mmol), piperazine (29.2 mmol) and N,N-diisopropylethylamine (DIPEA, 37.1 mmol) in acetonitrile (100 mL) was refluxed for 8 hours. The reaction progress was monitored by thin layer chromatography (TLC), and after complete conversion of the feedstock, the reaction mixture was cooled to room temperature. The solvent was removed by evaporation and the residue was purified by column chromatography to afford 1-(6-nitropyridin-3-yl)piperazine (8c). The product was a yellow solid in 82% yield.1H NMR (DMSO-d6, 400 MHz) δ: 7.96 (d, J = 9.3 Hz, 1H, Pyr-H), 7.88 (d, J = 2.9 Hz, 1H, Pyr-H), 7.26 (dd, J = 9.3, 3.0 Hz, 1H, Pyr-H), 3.64 (t, 4H, Pyr -NCH2CH2N), 3.32 (t, 4H, Pyr-NCH2CH2N).13C NMR (DMSO-d6, 100 MHz): δ 151.7, 146.2, 136.6, 125.9, 118.4, 51.3, 45.8. High-resolution mass spectrometry (HRMS, ESI): the calculated value for C9H12N4O2 [M + H]+is 209.1039 and the measured value is 209.1030. | [References]
[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 10, p. 4528 - 4560
[2] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 935 - 945
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1857 - 1872
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2388 - 2406
[5] Patent: WO2006/95159, 2006, A1. Location in patent: Page/Page column 77 |
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