205259-41-2

Basic information

• Product Name: Benzyl 2-amino-4-(benzyloxy)-5-methoxybenzoate
• Synonyms: Benzoic acid, 2-amino-5-methoxy-4-(phenylmethoxy)-, phenylmethyl ester;Benzyl 2-amino-4-(benzyloxy)-5-methoxybenzoate
• CAS NO: 205259-41-2
• Molecular Formula: C₂₂H₂₁NO₄
• Molecular Weight: 363.411
• Mol File: 205259-41-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 544.679 °C at 760 mmHg
• Flash Point: 216.221 °C
• Appearance: /
• Density: 1.215
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.617
• PKA: 2?+-.0.10(Predicted)
• CAS DataBase Reference: Benzyl 2-amino-4-(benzyloxy)-5-methoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 2-amino-4-(benzyloxy)-5-methoxybenzoate(205259-41-2)
• EPA Substance Registry System: Benzyl 2-amino-4-(benzyloxy)-5-methoxybenzoate(205259-41-2)

Safety Data

• Hazardous Substances Data: 205259-41-2(Hazardous Substances Data)

Usage

General Description

Benzyl 2-amino-4-(benzyloxy)-5-methoxybenzoate is a chemical compound with the molecular formula C28H25NO4. It is a benzyl ester derivative of 2-amino-4-(benzyloxy)-5-methoxybenzoic acid. Benzyl 2-amino-4-(benzyloxy)-5-methoxybenzoate is commonly used in organic synthesis and medicinal chemistry as a building block for the synthesis of various pharmaceuticals and bioactive molecules. It may also have potential applications in the development of new drug candidates and may exhibit biological activity, although further research is needed to fully understand its properties and potential uses.

InChI:InChI=1/C22H21NO4/c1-25-20-12-18(22(24)27-15-17-10-6-3-7-11-17)19(23)13-21(20)26-14-16-8-4-2-5-9-16/h2-13H,14-15,23H2,1H3

Upstream product

• 91203-74-6 4-benzyloxy-3-methoxybenzoic acid benzyl ester 
• 100-39-0 benzyl bromide 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 205259-40-1 4-benzyloxy-5-methoxy-2-nitrobenzoic acid benzyl ester 

Downstream Products

• 179688-01-8 7-(benzyloxy)-6-methoxyquinazolin-4(3H)-one 
• 387867-13-2 Tandutinib 
• 401903-53-5 4-[6-methoxy-7-(3-morpholin-4-yl-propoxy)-quinazolin-4-yl]-piperazine-1-carboxylic acid (4-isopropoxy-phenyl)-amide 

Relevant articles and documents

Fluorine-containing 6,7-dialkoxybiaryl-based inhibitors for phosphodiesterase 10 A: Synthesis and in vitro evaluation of inhibitory potency, selectivity, and metabolism

Based on the potent phosphodiesterase 10 A (PDE10A) inhibitor PQ-10, we synthesized 32 derivatives to determine relationships between their molecular structure and binding properties. Their roles as potential positron emission tomography (PET) ligands were evaluated, as well as their inhibitory potency toward PDE10A and other PDEs, and their metabolic stability was determined in vitro. According to our findings, halo-alkyl substituents at position 2 of the quinazoline moiety and/or halo-alkyloxy substituents at positions 6 or 7 affect not only the compounds′ affinity, but also their selectivity toward PDE10A. As a result of substituting the methoxy group for a monofluoroethoxy or difluoroethoxy group at position 6 of the quinazoline ring, the selectivity for PDE10A over PDE3A increased. The same result was obtained by 6,7-difluoride substitution on the quinoxaline moiety. Finally, fluorinated compounds (R)-7-(fluoromethoxy)-6-methoxy-4-(3-(quinoxaline-2-yloxy)pyrrolidine-1-yl) quinazoline (16 a), 19 a-d, (R)-tert-butyl-3-(6-fluoroquinoxalin-2-yloxy) pyrrolidine-1-carboxylate (29), and 35 (IC50 PDE10A 11-65 nM) showed the highest inhibitory potential. Further, fluoroethoxy substitution at position 7 of the quinazoline ring improved metabolic stability over that of the lead structure PQ-10. Fluor your health: Phosphodiesterase 10 A (PDE10A) has emerged as an attractive target for the development of 18F-labelled brain imaging agents for positron emission tomography. A series of fluorinated dialkoxybiaryl compounds were synthesized and evaluated as PDE10A inhibitors, assisted by QSAR docking studies. The 7-fluoromethoxy derivative appears to be a promising candidate for further development.

CHEMICAL PROCESS

The present invention relates to chemical processes for the manufacture of certain quinazoline derivatives, or pharmaceutically acceptable salts thereof. The invention also relates to processes for the manufacture of certain intermediates useful in the manufacture of the quinazoline derivatives and to processes for the manufacture of the quinazoline derivatives utilising said intermediates. In particular, the present invention relates to chemical processes and intermediates useful in the manufacture of the compound 4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline.

Potent and Selective Inhibitors of Platelet-Derived Growth Factor Receptor Phosphorylation. 3. Replacement of Quinazoline Moiety and Improvement of Metabolic Polymorphism of 4-[4-(N-Substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline Derivatives

We have previously reported that a series of 4-[4-(N-substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives were potent and selective inhibitors of platelet-derived growth factor receptor (PDGFR) phosphorylation and demonstrated several biological effects such as suppression of neointima formation following balloon injury in rat carotid artery by oral administration. Here, we investigated structure-activity relationships of the 6,7-dimethoxyquinazolinyl moiety. In regard to 6,7-dimethoxy groups, ethoxy analogues showed potent activity (IC50 of 16b is 0.04 μM; IC50 of 17a is 0.01 μM) and further extension of the alkyl group reduced activity. Interestingly, methoxyethoxy (IC50 of 16j is 0.02μM; IC50 of 17h is 0.01 μM) and ethoxyethoxy (IC50 of 17j is 0.02 μM) analogues showed the most potent activity, suggesting that the inserted oxygen atom significantly interacts with β-PDGFR. Among tricyclic quinazoline derivatives, the 2-oxoimidazo[4,5-e]quinazoline derivative 21a showed potent activity (IC 50 = 0.10 μM). Regarding replacements of quinazoline by other heterocyclic rings, pyrazolo[3,4-d]pyrimidine (39a, IC50 = 0.17 μM) and quinoline (IC50 of 40a is 0.18 μM; IC50 of 40b is 0.09 μM) derivatives showed potent activity. Isoquinoline and some pyridopyrimidine derivatives were completely inactive; therefore, 1-aza has an important role. Also 7-aza and 8-aza substitution on the parent quinazoline ring has a detrimental effect on the interaction with β-PDGFR. We also demonstrated that the substituents on the quinazoline ring possess major consequences for metabolic polymorphism. Although there existed extensive metabolizers and poor metabolizers in Sprague-Dawley rats administrated 6,7-dimethoxyquinazoline derivatives (1b and 1c), 6-(2-methoxy)ethoxy-7-methoxyquinazoline analogue 16k showed no metabolic polymorphism.