342417-04-3

Basic information

• Product Name: N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide
• Synonyms: NETUPITANT IST-2;N-?(tert-?Butyl)?-?6-?chloro-?4-?(2-?methylphenyl)?nicotinamide;3-Pyridinecarboxamide, 6-chloro-N-(1,1-dimethylethyl)-4-(2-methylphenyl)-
• CAS NO: 342417-04-3
• Molecular Formula: C₁₇H₁₉ClN₂O
• Molecular Weight: 302.79856
• EINECS: -0
• Mol File: 342417-04-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide(342417-04-3)
• EPA Substance Registry System: N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide(342417-04-3)

Safety Data

• Hazardous Substances Data: 342417-04-3(Hazardous Substances Data)

Usage

Description

N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide is a synthetic organic compound with a complex chemical structure. It is characterized by the presence of a nicotinamide core, which is substituted with a tert-butyl group, a chlorine atom, and an o-tolyl (2-methylphenyl) group. N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide is known for its potential applications in the pharmaceutical industry due to its unique chemical properties and interactions with biological targets.

Uses

Used in Pharmaceutical Industry:
N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide is used as a reagent for the synthesis of NK1/NK3 receptor antagonists. These antagonists are crucial in the development of novel treatments for depression, as they can modulate the activity of neurokinin receptors, which are involved in the regulation of mood and emotional responses. By targeting these receptors, N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide-based compounds may help alleviate depressive symptoms and improve the overall quality of life for patients suffering from this condition.

Upstream product

• 115309-58-5 N-tert-butyl-6-chloro-nicotinamide 
• 33872-80-9 o-tolyl magnesium chloride 
• 58757-38-3 6-Chloronicotinoyl chloride 
• 1634-04-4 tert-butyl methyl ether 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 

Downstream Products

• 342417-02-1 [6-(4-methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl]carbamic acid methyl ester 
• 342417-01-0 4-(2-methylphenyl)-6-(4-methylpiperazinyl)-3-pyridinecarboxamide 
• 342417-06-5 4-(2-methylphenyl)-6-(4-morpholinyl)-3-pyridinecarboxamide 
• 342417-07-6 [6-(morpholin-4-yl)-4-(o-tolyl)pyridin-3-yl]carbamic acid methyl ester 
• 290297-36-8 N-methyl-N-[6-(morpholin-4-yl)-4-(o-tolyl)pyridin-3-yl]amine 
• 290297-26-6 netupitant 
• 290296-68-3 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide 
• 290297-25-5 methyl-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-amine 
• 881743-64-2 N-tert-butyl-6-(4-methylpiperazin-1-yl)-4-(o-tolyl)nicotinamide 
• 342417-05-4 N-tert-butyl-6-(morpholin-4-yl)-4-(o-tolyl)nicotinamide 

Relevant articles and documents

NK1 receptor-targeting antagonist and application of same to chemotherapy-induced nausea and vomiting

The invention relates to a NK1 receptor-targeting antagonist and application of the same to chemotherapy-induced nausea and vomiting, belonging to the technical field of adjuvant therapeutics for tumor chemotherapy. The invention provides a compound as shown in a formula I which is described in the specification, or a racemate, stereoisomer, tautomer, isotopic label, oxynitride or pharmaceutically-acceptable salt thereof. The invention also provides a preparation method for the compound, a pharmaceutical compositions and the application of the compound or the racemate, stereoisomer, tautomer,isotopic label, oxynitride or pharmaceutically-acceptable salt thereof.

Research and development of an efficient process for the construction of the 2,4,5-substituted pyridines of NK-1 receptor antagonists

Roche has identified a 2,4,5-trisubstituted pyridine template for a new class of potent NK1 receptor antagonists. Previous strategies for construction of the pyridine core of these NK-1 receptor antagonists involved functionalization of a 2,5-disubstituted pyridine. We now report on construction of the pyridine core from commodity components. Shestopalov reported the synthesis of trans-4′-aryl-5′-cyano-1′,2′,3′, 4′-tetrahydro-6′-hydroxy-2′-oxo-1,3′-bipyridinium inner salts from 1-(2-amino-2-oxo-ethyl)pyridinium chloride, aromatic aldehydes, and ethyl cyanoacetate in the presence of a base. Reaction of these salts with phosphorus oxychloride affords 4-aryl-3-cyano-2,6-dichloropyridines. These are efficiently converted to nicotinamide precursors of the Roche NK-1 receptor antagonists by regioselective displacement of one chlorine by an amine, hydrogenolysis of the remaining chlorine, and nitrile hydrolysis.

4-phenyl-pyridine derivatives

The compounds of the related invention are related to 4-phenyl-pyridine derivatives connected by a bridge containing oxygen or nitrogen to a phenyl derivative.