tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate Chemical Properties

Melting point:

130-132℃

Boiling point:

454.1±45.0 °C(Predicted)

Density 

1.182

vapor pressure 

0-0Pa at 20-25℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Very Slightly)

form 

Solid

pka

7.36±0.26(Predicted)

color 

Dark Yellow

Sensitive 

Air Sensitive

InChI

InChI=1S/C14H22N4O2/c1-14(2,3)20-13(19)18-8-6-17(7-9-18)11-4-5-12(15)16-10-11/h4-5,10H,6-9H2,1-3H3,(H2,15,16)

InChIKey

RMULRXHUNOVPEI-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCN(C2=CC=C(N)N=C2)CC1

LogP

1.6-1.8 at 35℃ and pH7-9

Safety Information

HS Code 

2933599590

tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate Usage And Synthesis

Physical Form

Solid

Description

Tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate is a pharmaceutical intermediate compound that can be used to synthesize the targeted cancer drug Ribociclib for the treatment of ER-positive and HER2-negative breast cancer.

Uses

4-(6-Amino-3-pyridyl)-1-Boc-piperazine (tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate) is used as an organic chemical synthesis intermediate.

Preparation

4- (6-Nitro-pyridin-3-yl)-piperazine-1 -carboxylic acid ie f-butyl ester and Pd/C in ethanol is stirred with an H2 balloon for 3 h. The product tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate is obtained through purification.

Hazard

Causes skin irritation
Causes serious eye irritation
May cause respiratory irritation

Synthesis

General Steps: Example 101h Synthesis of tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate 101h To a 500 mL triple-necked vial under nitrogen protection was added tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 101g (3.1 g, 10 mmol), 10% palladium-carbon catalyst (50% wet, 1.0 g) and anhydrous ethanol (100 mL). The reaction system was evacuated and filled with hydrogen, and the reaction was stirred at room temperature for 16 hours. Upon completion of the reaction, the hydrogen was removed by evacuation and refilled with nitrogen for protection. The reaction mixture was filtered through a diatomaceous earth pad to remove the catalyst and the filtrate was concentrated under reduced pressure to give the target compound 101h (2.7 g, 97% yield). Mass spectral data: MS: [M + H]+ 279.

References

[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3125 - 3140
[2] Patent: WO2016/30439, 2016, A1. Location in patent: Page/Page column 30
[3] Patent: WO2011/140488, 2011, A1. Location in patent: Page/Page column 112; 270
[4] Patent: US2013/116262, 2013, A1. Location in patent: Paragraph 0315
[5] Patent: EP2773638, 2015, B1. Location in patent: Paragraph 0170; 0171; 1405

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