tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate
[CAS# 571188-59-5]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate
• Synonyms: 4-(6-Aminopyridin-3-yl)piperazine-1-carboxylic acid tert-butyl ester; 4-(6-Aminopyridin-3-yl)piperazine-1-carboxylic acid tert-butyl ester
• Molecular Formula: C₁₄H₂₂N₄O₂
• Molecular Weight: 278.35
• CAS Registry Number: 571188-59-5
• EC Number: 695-268-4
• SMILES: CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=C(C=C2)N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 454.1±45.0 °C 760 mmHg (Calc.)^*
• Flash point: 228.4±28.7 °C (Calc.)^*
• Index of refraction: 1.569 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H301-H302-H315-H317-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Acute hazardous to the aquatic environment	Aquatic Acute	3	H402
Acute toxicity	Acute Tox.	3	H301
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate is a chemical compound that belongs to a class of organic compounds known as piperazine derivatives. This molecule has several functional groups that contribute to its chemical and biological properties. The structure of the compound consists of a piperazine ring, which is substituted at the 4-position with a tert-butyl ester group and at the 3-position of the pyridine ring with an amino group.

The discovery and applications of this chemical have been primarily focused on its potential use in medicinal chemistry, specifically in the design of new pharmaceutical agents. The piperazine ring is a common feature in many bioactive compounds, including those used for treating central nervous system disorders, such as anxiety and depression, as well as other therapeutic areas like antihistamines, analgesics, and antiemetics. The addition of the pyridine ring and the amino group on the pyridine could influence the compound's ability to interact with various biological targets, particularly in the realm of receptor binding or enzyme inhibition.

While specific studies on tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate are limited in the public domain, derivatives of piperazine compounds with substituted pyridine rings have been shown to exhibit a variety of biological activities. This suggests that similar compounds, including the one in question, could potentially act as modulators of neurotransmitter systems or as inhibitors of certain enzymes or receptors that play key roles in various diseases.

As for its application in drug development, compounds with similar structural motifs have been investigated for their affinity for receptors such as serotonin, dopamine, and histamine, which are crucial for many therapeutic areas, including psychiatry and neurology. Moreover, the tert-butyl group in the structure provides steric protection and could affect the compound's pharmacokinetics, such as its lipophilicity, solubility, and stability, which are important for drug design.

The synthesis of this compound would typically involve the preparation of a piperazine derivative, followed by selective functionalization of the pyridine ring at the desired positions. Such synthetic strategies are crucial for the generation of libraries of related compounds, which can be tested for their biological properties and potential therapeutic effects.

In conclusion, while the specific uses of tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate are not well documented, its structural similarity to other bioactive piperazine derivatives suggests that it may have utility in the development of novel pharmaceuticals, particularly those targeting neurotransmitter systems or acting as enzyme inhibitors. Further research would be needed to explore its full potential in medicinal chemistry.

References

2016. A Two-Step Continuous-Flow Procedure towards Ribociclib. Journal of Flow Chemistry, 6(3).
DOI: 10.1556/1846.2016.00017

2019. A new route for the synthesis of Palbociclib. Chemical Papers, 73(12).
DOI: 10.1007/s11696-019-00841-7

2023. Development of novel palbociclib-based CDK4/6 inhibitors exploring the back pocket behind the gatekeeper. Investigational New Drugs, 41(5).
DOI: 10.1007/s10637-023-01385-0