383432-38-0

Basic information

• Product Name: 2-Methoxy-N-[(2E)-3-[4-[[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]phenyl]amino]-6-quinazolinyl]-2-propen-1-yl]acetamide
• Synonyms: 2-Methoxy-N-[(2E)-3-[4-[[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]phenyl]amino]-6-quinazolinyl]-2-propen-1-yl]acetamide;2-Methoxy-N-[(2E)-3-[4-[[3-Methyl-4-[(6-Methyl-3-pyridinyl)oxy]phenyl]aMino]-6-quinazolinyl]-2-prope;CP-724714 (E-Double bond);CP-724714(E)-2-methoxy-N-(3-(4-(3-methyl-4-(6-methylpyridin-3-yloxy)phenylamino)quinazolin-6-yl)allyl)acetamide;(E)-2-Methoxy-N-(3-(4-(3-methyl-4-(6-methylpyridin-3-yloxy)phenylamino)quinazolin-6-yl)allyl)a
• CAS NO: 383432-38-0
• Molecular Formula: C₂₇H₂₇N₅O₃
• Molecular Weight: 469.54
• Mol File: 383432-38-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 687.304 °C at 760 mmHg
• Flash Point: 369.468 °C
• Appearance: /
• Density: 1.251
• PKA: 13.95±0.46(Predicted)
• CAS DataBase Reference: 2-Methoxy-N-[(2E)-3-[4-[[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]phenyl]amino]-6-quinazolinyl]-2-propen-1-yl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-N-[(2E)-3-[4-[[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]phenyl]amino]-6-quinazolinyl]-2-propen-1-yl]acetamide(383432-38-0)
• EPA Substance Registry System: 2-Methoxy-N-[(2E)-3-[4-[[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]phenyl]amino]-6-quinazolinyl]-2-propen-1-yl]acetamide(383432-38-0)

Safety Data

• Hazardous Substances Data: 383432-38-0(Hazardous Substances Data)

Usage

Description

CP 724,714 is a selective inhibitor of HER2/ErbB2 with an IC50 value of 10 nM. It demonstrates greater than 640-fold selectivity against EGFR, InsR, IRG-1R, PDGFR, VEGFR2, Abl, Src, and c-Met. CP 724,714 has been shown to inhibit the proliferation of ErbB2-amplified cells, including BT474 and SK-BR-3 with IC50 values of 0.25 and 0.95 μM, respectively. It also demonstrates antitumor activity in various human tumor xenograft models. However, CP 724,714 was discontinued from clinical development due to hepatotoxicity caused by its ability to inhibit hepatic efflux transporters at low micromolar concentrations.

Uses

CP 724714 is a HER-2 tyrosine kinase inhibitor used in tumor treatments for HER2 positive solid tumors.

Upstream product

• 1121-78-4 5-Hydroxy-2-methylpyridine 
• 13290-74-9 1-chloro-2-methyl-4-nitrobenzene 
• 697299-78-8 2-methyl-5-(2-methyl-4-nitrophenoxy)pyridine 
• 537705-06-9 3-(2-methyl-4-aminophenoxy)-6-methylpyridine 
• 98556-31-1 4-chloro-6-iodoquinazoline 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 16064-08-7 6-iodo-4-hydroxyquinazoline 
• 537705-05-8 6-iodo-N-(3-methyl-4-((6-methylpyridin-3-yl)oxy)phenyl)quinazolin-4-amine 
• 486393-59-3 N-allyl-2-methoxyacetamide 
• 537705-10-5 (6-iodoquinazolin-4-yl)-[3-methyl-4-(6-methylpyridin-3-yloxy)phenyl]amine hydrochloride 
• 383433-14-5 (3-{4-[3-methyl-4-(6-methylpyridin-3-yloxy)phenylamino]quinazolin-6-yl}prop-2-ynyl)carbamic acid tert-butyl ester 
• 537705-07-0 N-propargyl-2-methoxyacetamide 
• 625-45-6 2-methoxyacetic acid 
• 38870-89-2 Methoxyacetyl chloride 

Downstream Products

• 719270-52-7 E-2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-allyl)-acetamide monofumarate 
• 719270-61-8 E-2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-allyl)-acetamide monobesylate 

Relevant articles and documents

Highly functionalised sulfur-based silica scavengers for the efficient removal of palladium species from active pharmaceutical ingredients

The use of multidentate sulfur-based silica scavengers 1,2, and 3 as highly effective adsorbents for the removal of precious metals, specifically palladium residues in this paper, from highly functionalised synthetic intermediates and APIs is described. The synthesis and purification of the polar and electron-rich reaction products, containing multiple functional groups, from palladium-catalysed removals of commonly used protecting groups such as benzyl, benzyloxycarbonyl, and allyloxycarbonyl and Sonogashira, Suzuki, Heck, and Buchwald-Hartwig coupling reactions is reported. The significant levels of residual palladium species, typically associated with these reaction products, are successfully and rapidly removed to below acceptable regulatory levels, of less than 5 ppm, by simple, unoptimised treatment with the designed silica scavengers at room temperature. Performance aspects, including broad solvent compatibility, excellent stability, and high metal affinity, combined with large-scale availability, ease of handling, and minimal loss of API make these silica scavengers particularly useful to process development groups.

Evaluation of kilogram-scale Sonagashira, Suzuki, and Heck coupling routes to oncology candidate CP-724,714

The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6- methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetainide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. A convergent and selective synthesis of the candidate was identified which utilizes a Heck coupling of a protected allylamine to install the critical olefin.

Selective erbB2 inhibitor/anti-erbB antibody combinations in the treatment of cancer

This invention relates to a method of treatment of cancer with a combination of an erbB2 ligand and an antibody, in mammals. More particularly, this invention relates to a method of treating cancer by administering an erbB2 ligand in combination with an erbB antibody. This invention also relates to a kit useful in the treatment of abnormal cell growth in mammals, especially humans.