156428-85-2

Basic information

• Product Name: 3-Methoxy-4-(4-Methylpiperazin-1-yl)aniline
• Synonyms: 3-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamine;3-Methoxy-4-(4-methyl-1-piperazinyl)aniline;3-Methoxy-4-(4-Methylpiperazin-1-yl)aniline;3-Methoxy-4-(4-Methyl-1-piperazinyl)-benzenaMine 3HCl;3-Methoxy-4-(4-methyl-1-piperazinyl)aniline 3HCl
• CAS NO: 156428-85-2
• Molecular Formula: C₁₂H₁₉N₃O
• Molecular Weight: 330.68158
• Mol File: 156428-85-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 394.869°C at 760 mmHg
• Flash Point: 192.61°C
• Appearance: /
• Density: 1.112g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.574
• PKA: 8.21±0.40(Predicted)
• CAS DataBase Reference: 3-Methoxy-4-(4-Methylpiperazin-1-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxy-4-(4-Methylpiperazin-1-yl)aniline(156428-85-2)
• EPA Substance Registry System: 3-Methoxy-4-(4-Methylpiperazin-1-yl)aniline(156428-85-2)

Safety Data

• Hazardous Substances Data: 156428-85-2(Hazardous Substances Data)

Usage

General Description

3-Methoxy-4-(4-Methylpiperazin-1-yl)aniline, also known as 4-Methoxy-3-(4-methyl-1-piperazinyl)benzenamine, is a chemical compound belonging to the class of anilines and piperazines. It is a pale yellow solid that is soluble in organic solvents and commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 3-Methoxy-4-(4-Methylpiperazin-1-yl)aniline has a wide range of applications, including as a building block in the production of various drugs, such as antipsychotics and antihistamines, and in the manufacturing of pesticides and herbicides. Its chemical structure and functional groups make it a versatile molecule for use in organic synthesis and medicinal chemistry. However, it is important to handle this compound with care due to its potential health hazards and toxic effects if not properly managed.

InChI:InChI=1/C12H19N3O/c1-14-5-7-15(8-6-14)11-4-3-10(13)9-12(11)16-2/h3-4,9H,5-8,13H2,1-2H3

Upstream product

• 109-01-3 1-methyl-piperazine 
• 77337-82-7 1-bromo-2-methoxy-4-nitrobenzene 
• 454-16-0 1-fluoro-2-methoxy-4-nitrobenzene 
• 1009-36-5 2-chloro-5-nitroanisole 
• 209482-01-9 1–(2-methoxy-4-nitrophenyl)-4-methylpiperazine 

Downstream Products

• 1126430-84-9 4-{2-(ethylamino)-4-[3-methyl-5-(methyloxy)phenyl]-1,3-thiazol-5-yl}-N-[3-(methyloxy)-4-(4-methyl-1-piperazinyl)phenyl]-2-pyrimidinamine 
• 1404437-49-5 N-(3-methoxy-4-(4-methylpiperazin-1-yl)phenyl)-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 1417795-19-7 C₂₄H₂₅N₅O 
• 1417795-22-2 C₂₄H₂₇ClN₄O₂ 
• 1417795-33-5 C₁₇H₂₁IN₄O 
• 1453207-83-4 5-[(2,6-difluoro-3,5-dimethoxyphenyl)ethynyl]-N-[3-methoxy-4-(4-methylpiperazin-1-yl)phenyl]pyrimidin-2-amine 
• 1453207-60-7 5-[2-(2,6-difluoro-3,5-dimethoxyphenyl)ethyl]-N-[3-methoxy-4-(4-methylpiperazin-1-yl)phenyl]pyrimidin-2-amine 

Relevant articles and documents

COMPOUNDS AND THEIR USES AS SPLEEN TYROSINE KINASE INHIBITORS

Provided are compounds of Formula (I) which can be used as Syk inhibitors and potently as therapeutic agents against diseases mediated by Syk.

The synthesis and bioactivity of pyrrolo[2,3-d]pyrimidine derivatives as tyrosine kinase inhibitors for NSCLC cells with EGFR mutations

EGFR mutations are an ongoing challenge in the treatment of NSCLC, and demand continuous updating of EGFR TKI drug candidates. Pyrrolopyrimidines are one group of versatile scaffolds suitable for tailored drug development. However not many precedents of this type of pharmacophore have been investigated in the realm of third generation of covalent EGFR-TKIs. Herein, a series of pyrrolo[2,3-d]pyrimidine derivatives able to block mutant EGFR activity in a covalent manner were synthesized, through optimized Buchwald-Hartwig C–N cross coupling reactions. Their preliminary bioactivity and corresponding inhibitory mechanistic pathways were investigated at molecular and cellular levels. Several compounds exhibited increased biological activity and enhanced selectivity compared to the control compound. Notably, compound 12i selectively inhibits HCC827 cells harboring the EGFR activating mutation with up to 493-fold increased efficacy compared to in normal HBE cells. Augmented selectivity was also confirmed by kinase enzymatic assay, with the test compound selectively inhibiting the T790 M activating mutant EGFRs (IC50 values of 0.21 nM) with up to 104-fold potency compared to the wild-type EGFR (IC50 values of 22 nM). Theoretical simulations provide structural evidence of selective kinase inhibitory activity. Thus, this series of pyrrolo[2,3-d]pyrimidine derivatives could serve as a starting point for the development of new EGFR-TKIs.

Pyrrolo [2, 3-d] pyrimidine derivative targeting EGFR mutation as well as preparation method and application of pyrrolo [2, 3-d] pyrimidine derivative

The invention provides a pyrrolo [2, 3-d] pyrimidine derivative targeting EGFR mutation as well as a preparation method and application thereof, and belongs to the field of chemical medicines. The derivative is a compound shown as a formula I, or a salt t