1008451-58-8

Basic information

• Product Name: 4-Chloro-2-Methoxynicotinaldehyde
• Synonyms: 4-Chloro-2-Methoxynicotinaldehyde;4-Chloro-2-Methoxypyridine-3-carbaldehyde;3-Pyridinecarboxaldehyde,4-chloro-2-methoxy-
• CAS NO: 1008451-58-8
• Molecular Formula: C₇H₆ClNO₂
• Molecular Weight: 171.58104
• Mol File: 1008451-58-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 257.5±35.0 °C(Predicted)
• Appearance: /
• Density: 1.317±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 2.37±0.10(Predicted)
• CAS DataBase Reference: 4-Chloro-2-Methoxynicotinaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-Methoxynicotinaldehyde(1008451-58-8)
• EPA Substance Registry System: 4-Chloro-2-Methoxynicotinaldehyde(1008451-58-8)

Safety Data

• Hazardous Substances Data: 1008451-58-8(Hazardous Substances Data)

Usage

Description

4-Chloro-2-Methoxynicotinaldehyde, also known as 4-Chloro-2-methoxypyridine-3-carbaldehyde, is an organic compound that serves as a key reactant in the synthesis of pharmaceuticals. It is characterized by its unique chemical structure, which includes a chloro group, a methoxy group, and a pyridine ring with a formyl group attached to the third position.

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-Methoxynicotinaldehyde is used as a reactant for the preparation of insulin-like growth factor 1 receptor (IGF-1R) inhibitors, specifically GTx-134. 4-Chloro-2-Methoxynicotinaldehyde plays a crucial role in the development of novel therapeutic agents targeting IGF-1R, which is implicated in various cancers and has potential applications in the treatment of these diseases.
The IGF-1R inhibitors, such as GTx-134, are designed to modulate the IGF-1R signaling pathway, which is often dysregulated in cancer cells, leading to uncontrolled cell growth and proliferation. By targeting this pathway, 4-Chloro-2-Methoxynicotinaldehyde contributes to the development of innovative cancer treatments that can potentially improve patient outcomes and survival rates.

Upstream product

• 72141-44-7 4-chloro-2-methoxypyridine 
• 109-72-8 n-butyllithium 
• 107-31-3 Methyl formate 
• 108-18-9 diisopropylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 64-17-5 ethanol 
• 140-29-4 phenylacetonitrile 

Downstream Products

• 1823-00-3 3-benzyl-5-trichloromethyl-[1,2,4]oxadiazole 

Relevant articles and documents

Development of a Stereoselective and Scalable Synthesis for the Potent Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor, BMT-297376; N-((R)-1-((cis)-4-(3-(Difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide

The current work describes a stereoselective and scalable route to N-((R)-1-((cis)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide (1) from readily available 1,4-dioxaspiro[4.5]decan-8-one. The developed process encompasses an efficient 1,4-trans-selective synthesis of (trans)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl methanesulfonate as the key intermediate and the use of Ellman sulfinamine methodology to install an alkyl amine in a stereoselective manner. Various synthetic routes were screened to accomplish a stereoselective and scalable protocol to access the title compound (1). This advancement enabled a competent route to the title compound in an enantioselective, safe, cost-effective, and scalable manner.

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.