380844-26-8

Basic information

• Product Name: Methyl 2-amino-5-(3-chloropropoxy)-4-Methoxybenzoate
• Synonyms: Methyl 2-amino-5-(3-chloropropoxy)-4-Methoxybenzoate;Benzoic acid, 2-aMino-5-(3-chloropropoxy)-4-Methoxy-, Methyl ester;2-amino-5-(3-chloropropoxy)-4-methoxyBenzoic acid methyl ester
• CAS NO: 380844-26-8
• Molecular Formula: C₁₂H₁₆ClNO₄
• Molecular Weight: 273.714
• Mol File: 380844-26-8.mol

Chemical Properties

• Melting Point: 96-98℃
• Boiling Point: 423.6°C at 760 mmHg
• Flash Point: 210°C
• Appearance: /
• Density: 1.232
• Vapor Pressure: 2.21E-07mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Methyl 2-amino-5-(3-chloropropoxy)-4-Methoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-amino-5-(3-chloropropoxy)-4-Methoxybenzoate(380844-26-8)
• EPA Substance Registry System: Methyl 2-amino-5-(3-chloropropoxy)-4-Methoxybenzoate(380844-26-8)

Safety Data

• Hazardous Substances Data: 380844-26-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoate is used as a building block in the synthesis of other organic compounds for its potential medical benefits. It is utilized in the development of new drugs, where it can be modified to create derivatives that contribute to the advancement of pharmaceutical products.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoate is used in the manufacturing of insecticides and herbicides. Its ability to act as a pesticide makes it a valuable component in the production of various agricultural products aimed at controlling pests and weeds.

InChI:InChI=1/C12H16ClNO4/c1-16-10-7-9(14)8(12(15)17-2)6-11(10)18-5-3-4-13/h6-7H,3-5,14H2,1-2H3

Upstream product

• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 380844-24-6 methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate 
• 929683-54-5 3-(3-chloropropoxy)-4-methoxybenzaldehyde 
• 621-59-0 isovanillin 
• 645-08-9 Isovanillic acid 
• 380844-22-4 methyl 3-(3-chloropropoxy)-4-methoxybenzoate 

Downstream Products

• 380844-28-0 methyl 5-(3-chloropropoxy)-2-{[(dimethylamino)methylene]amino}-4-methoxybenzoate 
• 692059-41-9 6-(3-chloropropoxy)-4-chloro-7-methoxyquinazoline 
• 912556-91-3 6-(3-chloropropoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-ylamine 
• 184475-35-2 gefitinib 
• 1259017-55-4 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl 4-(bis(4-fluorophenyl)methyl)piperazine-1-carbodithioate 
• 1259017-73-6 N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(3-chloropropoxy)-7-methoxyquina-zolin-4-amine 
• 1259017-72-5 N-(3-bromophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine 
• 1259017-50-9 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl 4-methylpiperazine-1-carbodithioate 
• 1259017-48-5 3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl 4-methylpiperazine-1-carbodithioate 
• 1259017-46-3 3-(4-(3-bromophenylamino)-7-methoxyquinazolin-6-yloxy)propyl 4-methylpiperazine-1-carbodithioate 
• 1259017-51-0 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl piperazine-1-carbodithioate 
• 1259017-53-2 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl morpholine-4-carbodithioate 
• 1259017-54-3 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl thiomorpholine-4-carbodithioate 
• 1006609-38-6 ethyl 3-(7-methoxy-6-(3-(4-phenylpiperazin-1-yl)propoxy)quinazolin-4-ylamino)-1H-pyrrole-2-carboxylate 

Relevant articles and documents

Anti-cancer drug gefitinib and analog intermediate electro-reduction preparation method thereof

The invention relates to an electroreduction preparation method of a 2-amino-4-methoxybenzoic acid derivative represented by a formula I, wherein the preparation reaction is defined in the specification, n is selected from 1, 2 and 3, X is selected from C

Four-membered heterocycles-containing 4-anilino-quinazoline derivatives as epidermal growth factor receptor (EGFR) kinase inhibitors

We report herein the design and synthesis of novel azaspirocycle or azetidine substituted 4-anilinoquinazoline derivatives. The EGFR inhibitory activities and in vitro antitumor potency of these newly synthesized compounds against two lung cancer cell lines HCC827 and A549 were evaluated. Most of the target compounds possess good inhibitory potency. In particular, compounds 21g with 2-oxa-6-azaspiro[3.4]octane substituent was found to possess higher EGFR inhibitory activities and similar antitumor potency comparing to the lead compound gefitinib with improved water solubility.

Novel EGFR inhibitors prepared by combination of dithiocarbamic acid esters and 4-anilinoquinazolines

On the basis of combination strategy, a novel series of EGFR inhibitors were designed and synthesized by combination of dithiocarbamic acid esters and 4-anilinoquinazolines. The effect of the synthesized compounds on cell proliferation was evaluated by MTT assay in three human cancer cell lines: MDA-MB-468, SK-BR-3 and HCT-116. Two compounds (11d and 11f) were found more potent against all three cell lines and five compounds (11a, 11d-11g) were found more potent against both MDA-MB-468 and SK-BR-3 than Lapatinib. SAR studies revealed that the substituents on C6 and C7 positions of quinazoline, the amine component of dithiocarbamate moiety and the linker greatly affected the activity. This work provides a promising new strategy for the preparation of potent tyrosine kinase inhibitors.

4-Quinazolinyloxy-diaryl ureas as novel BRAFV600E inhibitors

Aryl phenyl ureas with a 4-quinazolinoxy substituent at the meta-position of the phenyl ring are potent inhibitors of mutant and wild type BRAF kinase. Compound 7 (1-(5-tert-butylisoxazol-3-yl)-3-(3-(6,7-dimethoxyquinazolin-4-yloxy) phenyl)urea hydrochloride) exhibits good pharmacokinetic properties in rat and mouse and is efficacious in a mouse tumor xenograft model following oral dosing.

Design, synthesis, and in vitro antitumor activity evaluation of novel 4-pyrrylamino quinazoline derivatives

Here, we describe the design and synthesis of two series of 4-pyrrylamino quinazolines as new analogs of the epidermal growth factor receptor inhibitor gefitinib. In vitro antitumor activity of these novel compounds against pancreatic (Miapaca2) and prostate (DU145) cancer cell lines was evaluated. Compared with the parental gefitinib, all 18 derivatives show a greatly increased cytotoxicity to cancer cells. In vitro kinase inhibitory activity on epidermal growth factor receptor was also investigated. Among them, compounds GI-6, GII-4, GII-6, GII-8, and GII-9 are more potential receptor tyrosine kinase (RTK) inhibitors. Based on these results, we propose simple structure-activity relationship to provide information for designing and developing more potent antitumor agents.

Design, synthesis of novel quinazolone alkaloids derivatives as potential antitumor agents

Several novel quinazolone alkaloids derivatives were synthesized. Some of the target compounds were determined against human prostate cancer DU145 and pancreatic cancer Miacapa2 cells in vitro. The entire compounds had been identified by 1HNMR, 13CNMR, IR, MS and EA.

Design and synthesis of novel Gefitinib analogues with improved anti-tumor activity

There is an urgent need to design and develop new and more potent EGFR inhibitors with improved anti-tumor activity. Here we describe the design and synthesis of two series of 4-benzothienyl amino quinazolines as new analogues of the EGFR inhibitor Gefiti

Design, synthesis, docking and antitumor activity of quinazolino [3, 4-a] thieno [3, 2-d] pyrimidin-8-one derivatives

Several novel quinazolino [3, 4-a] thieno [3, 2-d] pyrimidin-8-one derivatives were synthesized. All of the compounds were determined against MiaPaCa2 and DU145 cells in vitro, and the crystal structures of analog 8 and 20 in the active site of the EGFR c

QUINAZOLINE DERIVATIVES AS RAF KINASE MODULATORS AND METHODS OF USE THEREOF

Compounds according to formula (I), compositions and methods are provided for modulating the activity of RAF kinases, including BRAF kinase and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder mediated by RAF kinases. Formula (I): or a pharmaceutically acceptable salt, solvate, clathrate of hydrate thereof, wherein X is O or S(O)t; Ra is O or S.

Synthesis of gefitinib from methyl 3-hydroxy-4-methoxy-benzoate

This paper reports a novel synthesis of gefitinib starting from methyl 3-hydroxy-4-methoxybenzoate. The process starts with alkylation of the starting material, followed by nitration, reduction, cyclization, chlorination and two successive amination reactions. The intermediates and target molecule were characterized by 1H-NMR, 13C-NMR, MS and the purities of all these compounds were determined by HPLC. This novel synthetic route produced overall yields as high as 37.4%.