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ChemicalBook >> CAS DataBase List >>Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

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
Last updated:2025-07-24 18:13:48

Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate Properties

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)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
HS Code  2933599590
NFPA 704
1
2 0

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
Product number Packaging Price Buy
B810175 1g $60 Buy
OR54564 5g $89 Buy
CS-B0331 5g $59 Buy
4H56-1-0QN 5G $98 Buy
CS-B0331 10g $106 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

1-(6-nitropyridin-3-yl)piperazine

775288-71-6

Di-tert-butyl dicarbonate

24424-99-5

Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

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

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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
Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate pictures 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.
1-BOC-4-(6-NITROPYRIDIN-3-YL)PIPERAZINE pictures 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

571189-16-7(Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate)Related Search:

1-BOC-4-(6-NITROPYRIDIN-3-YL)PIPERAZINE 4-(6-Nitropyridin-3-yl)piperazine-1-carboxylic acid tert-butyl ester NaMe:4-(6-Nitro-3-pyridinyl)-1-piperazinecarboxylic acid tert-butyl ester Tert. butyl-4-(6-Nitropyridin-3-yl)piperazino-1-carboxylate 1-Piperazinecarboxylic acid, 4-(6-nitro-3-pyridinyl)-, 1,1-diMethylethyl ester 4-(6-nitropyridin-3-yl)-1-piperazinecarboxylic acid tert-butyl ester 4-(6-nitro-3-pyridinyl)-1-piperazinecarboxylic acid,1,1-dimethylethyl ester 4-(6-Nitropyridin-3-yl)piperazine, N1-Boc protected 1-Boc-4-(6-Nitro-3-Pyridyl)Piperazine 4-(6-Nitropyridin-3-yl)piperazine, N1-BOC protected 97% tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 4-(6-Nitro-3-pyridinyl)-1-piperazinecarboxylic acid tert-butyl ester 1-Boc-4-(6-nitropyridin-3-yl)piperazime Palbociclib Impurity 111 4-(6-Nitro-3-pyridyl)-piperazine-1-carboxylate 571189-16-7 Anticancer