167263-04-9

Basic information

• Product Name: TERT-BUTYL 4-CYANO-4-(PYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE
• Synonyms: TERT-BUTYL 4-CYANO-4-(PYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE;1-Piperidinecarboxylic acid, 4-cyano-4-(2-pyridinyl)-, 1,1-diMethylethyl ester;1-Boc-4-cyano-4-(2-pyridinyl)-piperidine;tert-Butyl 4-cyano-4-(pyridin-2-yl)
• CAS NO: 167263-04-9
• Molecular Formula: C16H21N3O2
• Molecular Weight: 287.36
• EINECS: 200-258-5
• Mol File: 167263-04-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 444.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 5.43±0.19(Predicted)
• CAS DataBase Reference: TERT-BUTYL 4-CYANO-4-(PYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 4-CYANO-4-(PYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE(167263-04-9)
• EPA Substance Registry System: TERT-BUTYL 4-CYANO-4-(PYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE(167263-04-9)

Safety Data

• Hazardous Substances Data: 167263-04-9(Hazardous Substances Data)

Usage

General Description

TERT-BUTYL 4-CYANO-4-(PYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE is a chemical compound that belongs to the piperidine carboxylate class. It is a tert-butyl ester derivative of pyridinylpiperidine carboxylate and contains a cyano group. TERT-BUTYL 4-CYANO-4-(PYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE is commonly used in the field of medicinal chemistry as a building block for the synthesis of various pharmaceutical agents. Its structure contains a piperidine ring with a pyridinyl group and a tert-butyl ester, making it useful in the development of new drugs and pharmaceuticals.

Upstream product

• 372-48-5 2-fluoropyridine 
• 2739-97-1 pyridine-2-acetonitrile 
• 118753-70-1 N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine 
• 91419-52-2 1-tert-butoxycarbonyl-4-cyanopiperidine 

Relevant articles and documents

POLYCYCLIC AMINES AS OPIOID RECEPTOR MODULATORS

The present invention provides a genus of polycyclic amines that are useful as opioid receptor modulators. The compounds of the invention are useful in both therapeutic and diagnostic methods, including for treating pain, neurological disorders, cardiac disorders, bowel disorders, drug and alcohol addiction, drug overdose, urinary disorders, respiratory disorders, sexual dysfunction, psoriasis, graft rejection or cancer.

Discovery of a selective allosteric M1 receptor modulator with suitable development properties based on a quinolizidinone carboxylic acid scaffold

One approach to ameliorate the cognitive decline in Alzheimer's disease (AD) has been to restore neuronal signaling from the basal forebrain cholinergic system via the activation of the M1 muscarinic receptor. A number of nonselective M1 muscarinic agonists have previously shown positive effects on cognitive behaviors in AD patients, but were limited due to cholinergic adverse events thought to be mediated by the activation of the M2 to M5 subtypes. One strategy to confer selectivity for M1 is the identification of positive allosteric modulators, which would target an allosteric site on the M1 receptor rather than the highly conserved orthosteric acetylcholine binding site. Quinoline carboxylic acids have been previously identified as highly selective M1 positive allosteric modulators with good pharmacokinetic and in vivo properties. Herein is described the optimization of a novel quinolizidinone carboxylic acid scaffold with 4-cyanopiperidines being a key discovery in terms of enhanced activity. In particular, modulator 4i gave high plasma free fractions, enhanced central nervous system (CNS) exposure, was efficacious in a rodent in vivo model of cognition, and afforded good physicochemical properties suitable for further preclinical evaluation.

Preparation of 4-heteroaryl-4-cyanopiperidines via SNAr substitution reactions

The scope and limitations of SNAr substitution reactions of metalated 4-cyanopiperidines with heterocyclic halides were explored. These facile reactions provide rapid access to a wide range of 4-heteroaryl-4-cyanopiperidines and have resulted i