1032452-86-0

Basic information

• Product Name: 3-(2-chloropyriMidin-4-yl)-1-Methylindole
• Synonyms: 3-(2-chloropyriMidin-4-yl)-1-Methylindole;3-(2-chloropyriMidin-4-yl)-1-Methyl-1H-indole;3-(2-Chloro-4-pyrimidinyl)-1-methyl-1H-indole;elagolix intermediate 11;EOS-61220
• CAS NO: 1032452-86-0
• Molecular Formula: C₁₃H₁₀ClN₃
• Molecular Weight: 243.6916
• EINECS: 1592732-453-0
• Product Categories: AZD9291
• Mol File: 1032452-86-0.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 486.3±28.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.89±0.31(Predicted)
• CAS DataBase Reference: 3-(2-chloropyriMidin-4-yl)-1-Methylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-chloropyriMidin-4-yl)-1-Methylindole(1032452-86-0)
• EPA Substance Registry System: 3-(2-chloropyriMidin-4-yl)-1-Methylindole(1032452-86-0)

Safety Data

• Hazardous Substances Data: 1032452-86-0(Hazardous Substances Data)

Usage

General Description

3-(2-chloropyriMidin-4-yl)-1-Methylindole is a chemical compound with the molecular formula C14H11ClN2. It falls under the category of indoles, which are heterocyclic aromatic organic compounds. This particular compound has a chlorine atom substituted on the pyrimidine ring and a methyl group attached on the indole ring. It is commonly used in chemical research, possibly for the synthesis of other complex organic molecules or as a reference compound in analytical studies. However, detailed information regarding its properties or applications is not readily available suggesting that it might be a specifically synthesized product designed for a particular research problem.

Upstream product

• 120-72-9 indole 
• 3934-20-1 2,6-Dichloropyrimidine 
• 75-16-1 methylmagnesium bromide 
• 129271-98-3 1-(phenylsulfonyl)-1H-indol-3-ylboronic acid 
• 882562-58-5 3-(2-chloropyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole 
• 945016-63-7 3-(2-chloro-pyrimidin-4-yl)-1H-indole 
• 50-00-0 formaldehyd 
• 1722-12-9 2-chloropyrimidine 
• 603-76-9 1-methylindole 
• 74-88-4 methyl iodide 

Downstream Products

• 1032452-85-9 trans-4-[4-(1-methyl-1H-indol-3-yl)-pyrimidin-2-ylamino]-cyclohexanol 
• 1421373-08-1 N-(4-bromo-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine 
• 1421372-94-2 N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indole-3-yl)-pyrimidine-2-amine 
• 1421373-86-5 C₂₉H₃₀N₆O₂ 
• 1421373-88-7 C₂₉H₃₃N₇O₂ 
• 1421373-99-0 Ν-(4-methoxy-2-(methyl(2-(methylamino)ethyl)amino)-5-((4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)amino)phenyl)acrylamide 
• 1421372-66-8 N?2?[[2?(dimethylamino)ethyl]methylamino]?4?methoxy?5?[[4?(1?methyl?1H?indole-3-yl)-2-pyrimidinyl]amino]aniline 
• 1421372-67-9 N¹-(2-(dimethylamino)ethyl)-5-methoxy-N¹-methyl-N⁴-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine 
• 1421372-69-1 4-[(3R)-3-dimethylaminopyrrolidin-1-yl]-6-methoxy-N-[4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,3-diamine 
• 1421372-70-4 N-[4-[(3R)-3-dimethylaminopyrrolidin-1-yl]-2-methoxy-5-nitrophenyl]-4-(1-methylindol-3-yl)pyrimidin-2-amine 
• 1421372-75-9 6-methoxy-N¹-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-4-(4-methylpiperazin-1-yl)benzene-1,3-diamine 
• 1421372-76-0 N-(4-(4-methylpiperazinyl)-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indole-3-yl)pyrimidin-2-yl-amine 
• 1421372-81-7 4-(3-(dimethylamino)cycloazane-1-yl)-6-methoxy-N₁-[4-(1-methylindol-3-yl)pyrimidine- 2-yl]benzene-1,3-diamine 
• 1421372-82-8 N-(2-methoxy-4-(3-(dimethylamino)cycloazan-1-yl)-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidine-2-amine 

Relevant articles and documents

Design, synthesis and biological evaluation of AZD9291 derivatives as selective and potent EGFRL858R/T790M inhibitors

Third-generation epidermal growth factor receptor (EGFR)L858R/T790M inhibitors are still the main drugs for the treatment of advanced non-small cell lung cancer (NSCLC), and these drugs have achieved remarkable clinical efficacy. However, there are still many patients suffering from drug-resistant mutations and drug side effects caused by NSCLC. In this study, guided by the molecular simulation, we applied a structure-based drug design strategy (SBDD) and optimized the structure to obtain a series of potent and selective EGFRL858R/T790M inhibitors. The most potent compound 18e demonstrated excellent kinase inhibitory activity and selectivity for EGFRL858R/T790M double mutants and the IC50 value reached nanomolar level. The selectivity of 18e against wild-type EGFR was near to 200-fold. In addition, compound 18e also inhibited H1975 cells proliferation at G2/M phase and induced apoptosis at a concentration of 0.25 μM, which makes it more valuable for potential lung cancer research.

A novel and efficient synthesis of anti-cancer agent, mereletinib

A convenient route for the synthesis of a third-generation epidermal growth factor receptor inhibitor, mereletinib (AZD9291) using starting materials that are commercially available has been achieved through reactions that are readily conducted under mild conditions. Importantly, a 5 g scale synthesis was also accomplished and this method could therefore be useful in the synthesis of similar drugs.

Discovery of highly potent and selective EGFRT790M/L858R TKIs against NSCLC based on molecular dynamic simulation

Epidermal growth factor receptor (EGFR) is the most attractive target for drug research in non-small cell lung cancer (NSCLC). There have been three generation drugs developed to treat of NSCLC. The third-generation EGFR tyrosine kinase inhibitors (TKIs)

Design, synthesis and biological evaluation of 2-aminopyrimidine-based LSD1 inhibitors

AZD9291, with excellent pharmaceutical properties, has been reported to have certain LSD1 inhibitory activity. Therefore, we carried out structural optimization based on the AZD9291 skeleton to increase the LSD1 inhibitory potential of the compound. Then, a series of 2-aminopyrimidine derivatives were designed and synthesized as LSD1 inhibitors, and their structure–activity relationships were studied. The most promising compound, X43, with an IC50 of 0.89 μM showed remarkable LSD1 selectivity not only to EGFRwt (>100-fold) but also to MAO-A/B (>50-fold). Further studies showed that X43 inhibited LSD1 activity and induced the apoptosis of A549 cells in a dose-dependent manner. Meanwhile, compound X43 showed a superior ability to inhibit the proliferation of A549 and THP-1 cells, with IC50 values of 1.62 μM and 1.21 μM, respectively. Then, analyses of the stability of human liver microsomes, CYP inhibition and in vivo pharmacokinetics in rats showed that X43 had favorable profiles in vitro and in vivo and the potential for further study. Our findings suggested that a 2-aminopyrimidine-based LSD1 inhibitor deserves further investigation as a treatment for LSD1-overexpressing cancer.

P-phenylenediamine LSD1 inhibitor and preparation method thereof

Disclosed are a p-phenylenediamine derivative as represented by general formula I, a pharmaceutically acceptable salt, and a stereoisomer thereof. The p-phenylenediamine derivative as represented by general formula I, the pharmaceutically acceptable salt thereof and the stereoisomer thereof can be used alone or in combination as lysine-specific demethylase-1 (LSD1) inhibitors.