Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate
- CAS No.
- 571189-16-7
- Chemical Name:
- Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate
- Synonyms
- tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate;4-(6-Nitro-3-pyridinyl)-1-piperazinecarboxylic acid tert-butyl ester;Palbociclib Impurity 111;1-Boc-4-(6-Nitro-3-Pyridyl)Piperazine;1-BOC-4-(6-NITROPYRIDIN-3-YL)PIPERAZINE;1-Boc-4-(6-nitropyridin-3-yl)piperazime;4-(6-Nitro-3-pyridyl)-piperazine-1-carboxylate;4-(6-Nitropyridin-3-yl)piperazine, N1-Boc protected;4-(6-Nitropyridin-3-yl)piperazine, N1-BOC protected 97%;Tert. butyl-4-(6-Nitropyridin-3-yl)piperazino-1-carboxylate
- CBNumber:
- CB72467082
- Molecular Formula:
- C14H20N4O4
- Molecular Weight:
- 308.33
- MDL Number:
- MFCD11849291
- MOL File:
- 571189-16-7.mol
- MSDS File:
- SDS
Boiling point | 480.1±45.0 °C(Predicted) |
---|---|
Density | 1.258 |
storage temp. | Inert atmosphere,Room Temperature |
pka | 0.11±0.70(Predicted) |
InChI | InChI=1S/C14H20N4O4/c1-14(2,3)22-13(19)17-8-6-16(7-9-17)11-4-5-12(15-10-11)18(20)21/h4-5,10H,6-9H2,1-3H3 |
InChIKey | SUWKOEMQNOBJEQ-UHFFFAOYSA-N |
SMILES | N1(C(OC(C)(C)C)=O)CCN(C2=CC=C([N+]([O-])=O)N=C2)CC1 |
SAFETY
Risk and Safety Statements
Symbol(GHS) | ![]() GHS07 |
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Signal word | Warning | |||||||||
Hazard statements | H315-H319-H335 | |||||||||
Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a | |||||||||
HS Code | 2933599590 | |||||||||
NFPA 704 |
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Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate price More Price(25)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
TRC | B810175 | tert-Butyl4-(6-Nitropyridin-3-yl)piperazine-1-carboxylate | 571189-16-7 | 1g | $60 | 2021-12-16 | Buy |
Apolloscientific | OR54564 | 4-(6-Nitropyridin-3-yl)piperazine,N1-BOCprotected 97% | 571189-16-7 | 5g | $89 | 2021-12-16 | Buy |
ChemScene | CS-B0331 | 1-Piperazinecarboxylicacid,4-(6-nitro-3-pyridinyl)-,1,1-dimethylethylester 96.47% | 571189-16-7 | 5g | $59 | 2021-12-16 | Buy |
SynQuest Laboratories | 4H56-1-0QN | 4-(6-Nitropyridin-3-yl)piperazine, N1-Boc protected | 571189-16-7 | 5G | $98 | 2021-12-16 | Buy |
ChemScene | CS-B0331 | 1-Piperazinecarboxylicacid,4-(6-nitro-3-pyridinyl)-,1,1-dimethylethylester 96.47% | 571189-16-7 | 10g | $106 | 2021-12-16 | Buy |
Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate Chemical Properties,Uses,Production
Description
Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate is a pharmaceutical intermediate compound that can be used to synthesize the anticancer drug Palbociclib. Palbociclib is used to treat estrogen receptor-positive (ER+) and human epidermal growth factor receptor-negative (HER2-) breast cancer.
Uses
tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate is used in preparation of Heterocyclic compound as cdk-hdac double-channel inhibitor.
Synthesis

775288-71-6

24424-99-5

571189-16-7
1-(6-nitropyridin-3-yl)piperazine (15.6 g, 0.075 mol) was suspended in 120 mL of tetrahydrofuran (THF) under nitrogen protection. Triethylamine (10.5 mL, 0.075 mol) and 4-dimethylaminopyridine (0.46 g, 5 mol%) were added sequentially to the suspension. Di-tert-butyl dicarbonate (16.6 g, 0.075 mol) was dissolved in 50 mL of THF and transferred to a dropping funnel. The solution was slowly added dropwise to the stirred suspension, and the rate of dropwise acceleration was controlled to maintain the reaction temperature below 27 °C. After dropwise addition, the reaction mixture was cooled to room temperature and subsequently heated to reflux. After refluxing the reaction for 1 hour, a small amount of insoluble material was removed by filtration. The solvent was removed by concentration under reduced pressure and the yellow residue was partitioned between ethyl acetate (EtOAc) and water. The aqueous phase was extracted twice with EtOAc. The organic layers were combined, washed sequentially with a small amount of water and saturated sodium chloride solution, dried and concentrated under reduced pressure. The resulting solid was recrystallized by 2-propanol (treated with activated charcoal) to give the target product tert-butyl 4-(6-nitro-3-pyridinyl)-1-piperazinecarboxylate, ca. 19 g (yield ca. 80%). Nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3) δ: 1.49 (s, 9H), 3.46 (m, 4H), 3.65 (m, 4H), 7.20 (m, 1H), 8.17 (m, 2H). Mass spectrum (m/z): 309.
References
[1] Patent: WO2006/95159, 2006, A1. Location in patent: Page/Page column 77-78
[2] British Journal of Pharmacology, 2018, vol. 175, # 12, p. 2399 - 2413
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2388 - 2406
[4] Patent: WO2006/8545, 2006, A2. Location in patent: Page/Page column 153
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 22, p. 7938 - 7957
Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate Preparation Products And Raw materials
Raw materials
1of2
Preparation Products
Supplier | Tel | Country | ProdList | Advantage | |
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ChemExpress | +86-19370970350 +86-021-58950125 | info@chemexpress.com | China | 785 | 58 |
Capot Chemical Co.,Ltd. | +8613336195806 | sales@capot.com | China | 29731 | 60 |
Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21622 | 55 |
ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 33024 | 60 |
career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29855 | 58 |
Jinan Carbotang Biotech Co.,Ltd. | +8615866703830 | figo.gao@foxmail.com | China | 8497 | 58 |
Jinan Shengqi pharmaceutical Co,Ltd | 86+18663751872 | christine@shengqipharm.com | CHINA | 491 | 58 |
Jinan Finer Chemical Co., Ltd | +86-531-88989536 +86-15508631887 | sales@finerchem.com | China | 2955 | 58 |
CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49733 | 58 |
Shaanxi Dideu Medichem Co. Ltd | +86-29-87569266 15319487004 | 1015@dideu.com | China | 3969 | 58 |
View Lastest Price from Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
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2023-06-15 | Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate
571189-16-7
|
US $0.00-0.00 / Kg | 1Kg | 98%;USP/EP/CP | 1-10000kgs | Changzhou Rokechem Technology Co., Ltd. | |
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2019-07-06 | 1-BOC-4-(6-NITROPYRIDIN-3-YL)PIPERAZINE
571189-16-7
|
US $1.00 / KG | 1KG | 99% | Customized | Career Henan Chemical Co |
-
- Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate
571189-16-7
- US $0.00-0.00 / Kg
- 98%;USP/EP/CP
- Changzhou Rokechem Technology Co., Ltd.
-
- 1-BOC-4-(6-NITROPYRIDIN-3-YL)PIPERAZINE
571189-16-7
- US $1.00 / KG
- 99%
- Career Henan Chemical Co