827602-53-9

Basic information

• Product Name: 5-BROMO-3-[(4-METHOXYBENZYL)AMINO]PYRAZIN-2-AMINE
• Synonyms: 5-BROMO-3-[(4-METHOXYBENZYL)AMINO]PYRAZIN-2-AMINE
• CAS NO: 827602-53-9
• Molecular Formula: C₁₂H₁₃BrN₄O
• Molecular Weight: 0
• Mol File: 827602-53-9.mol

Chemical Properties

• Boiling Point: 450.3°C at 760 mmHg
• Flash Point: 226.1°C
• Appearance: /
• Density: 1.557g/cm³
• Vapor Pressure: 2.68E-08mmHg at 25°C
• Refractive Index: 1.681
• CAS DataBase Reference: 5-BROMO-3-[(4-METHOXYBENZYL)AMINO]PYRAZIN-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-3-[(4-METHOXYBENZYL)AMINO]PYRAZIN-2-AMINE(827602-53-9)
• EPA Substance Registry System: 5-BROMO-3-[(4-METHOXYBENZYL)AMINO]PYRAZIN-2-AMINE(827602-53-9)

Safety Data

• Hazardous Substances Data: 827602-53-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H13BrN4O/c1-18-9-4-2-8(3-5-9)6-16-12-11(14)15-7-10(13)17-12/h2-5,7H,6H2,1H3,(H2,14,15)(H,16,17)

Upstream product

• 2393-23-9 4-methoxy-benzylamine 
• 24241-18-7 2-amino-3,5-dibromopyrazine 

Downstream Products

• 1399857-81-8 1-(4-methoxybenzyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine 
• 1399857-79-4 6-(4-fluorophenyl)-1-(4-methoxybenzyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine 
• 1021918-21-7 (3-amino-6-(5-quinolinyl)pyrazin-2-yl)[(4-methoxyphenyl)methyl]amine 
• 827602-54-0 N-[5-bromo-3-(4-methoxy-benzylamino)-pyrazin-2-yl]-formamide 

Relevant articles and documents

Discovery of a novel class of exquisitely selective mesenchymal-epithelial transition factor (c-MET) protein kinase inhibitors and identification of the clinical candidate 2-(4-(1-(Quinolin-6-ylmethyl)-1 H -[1,2,3]triazolo[4,5- b ]pyrazin-6-yl)-1 H -pyrazol-1-yl)ethanol (PF-04217903) for the treatment of cancer

The c-MET receptor tyrosine kinase is an attractive oncology target because of its critical role in human oncogenesis and tumor progression. An oxindole hydrazide hit 6 was identified during a c-MET HTS campaign and subsequently demonstrated to have an unusual degree of selectivity against a broad array of other kinases. The cocrystal structure of the related oxindole hydrazide c-MET inhibitor 10 with a nonphosphorylated c-MET kinase domain revealed a unique binding mode associated with the exquisite selectivity profile. The chemically labile oxindole hydrazide scaffold was replaced with a chemically and metabolically stable triazolopyrazine scaffold using structure based drug design. Medicinal chemistry lead optimization produced 2-(4-(1-(quinolin-6- ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)-1H-pyrazol-1-yl)ethanol (2, PF-04217903), an extremely potent and exquisitely selective c-MET inhibitor. 2 demonstrated effective tumor growth inhibition in c-MET dependent tumor models with good oral PK properties and an acceptable safety profile in preclinical studies. 2 progressed to clinical evaluation in a Phase I oncology setting.

HETEROARYL COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH

Provided herein are Heteroaryl Compounds having the following structure: (I) wherein R1, R2, L, X, Y, Z, Q, A and B are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a patient in need thereof.

ARYLMETHYL TRIAZOLO AND IMIDAZOPYRAZINES AS C-MET INHIBITORS

The present invention relates to compounds of the Formulae (I) - (IV), wherein R1 - R6, R11 - R13, X and Y are defined herein, and their pharmaceutically acceptable salts. These compounds modulate the activity of c-Met and are therefore expected to be useful in the prevention and treatment of c-Met related disorders such as cancer.