849235-68-3

Basic information

• Product Name: 4-({[4-(Pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid
• Synonyms: 4-({[4-(Pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid
• CAS NO: 849235-68-3
• Molecular Formula: C₁₇H₁₄N₄O₂
• Molecular Weight: 306.31866
• Mol File: 849235-68-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 608.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.348±0.06 g/cm3(Predicted)
• PKA: 4.24±0.10(Predicted)
• CAS DataBase Reference: 4-({[4-(Pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-({[4-(Pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid(849235-68-3)
• EPA Substance Registry System: 4-({[4-(Pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid(849235-68-3)

Safety Data

• Hazardous Substances Data: 849235-68-3(Hazardous Substances Data)

Upstream product

• 350-03-8 methyl-3-pyridylketone 
• 736080-30-1 4-guanidinomethylbenzoic acid methyl ester 
• 55314-16-4 (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 1571-08-0 methyl 4-formylbenzoate 
• 849235-67-2 methyl 4-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)benzoate 
• 55314-16-4 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 66521-66-2 4-pyridin-3-ylpyrimidin-2-ylamine 

Downstream Products

• 726169-73-9 mocetinostat 
• 1448350-10-4 N-(2-amino-4-methoxyphenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-19-3 N-(4-{[(tert-butyldimethylsilyl)oxy]methyl}-2-nitrophenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-18-2 N-(4-bromo-2-nitrophenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-17-1 N-(2-nitro-4-phenylphenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-08-0 N-(2-amino-4-phenylphenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-09-1 N-(2-amino-4-bromophenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-11-5 N-(2-amino-4-hydroxyphenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-12-6 N-(2-amino-4-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-13-7 N-[2-amino-4-(hydroxymethyl)phenyl]-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide 
• 1448350-20-6 benzyl 3-nitro-4-{[4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzene]amido}benzoate 
• 1448350-14-8 benzyl 3-amino-4-[4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamido]benzoate 
• 1448350-15-9 3-amino-4-[4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamido]benzoic acid 
• 944537-89-7 N-(2-aminophenyl)-4-((4-(pyridin-3-yl)pyrimidin-2-ylamino)methyl)benzamide dihydrobromide 

Relevant articles and documents

Synthesis, Biological Activities and Docking Studies of Novel 4-(Arylaminomethyl)benzamide Derivatives as Potential Tyrosine Kinase Inhibitors

A number of new compounds containing the 4-(aminomethyl)benzamide fragment as a linker were designed and synthesized, and their biological activities were evaluated as potential anticancer agents. The cytotoxicity activity of the designed compounds was studied in two hematological and five solid cell lines in comparison with the reference drugs. Targeted structures against eight receptor tyrosine kinases including EGFR, HER-2, HER-4, IGF1R, InsR, KDR, PDGFRa, and PDGFRb were investigated. The majority of the compounds showed a potent inhibitory activity against the tested kinases. The analogues 11 and 13 with the (trifluoromethyl)benzene ring in the amide or amine moiety of the molecule were proven to be highly potent against EGFR, with 91% and 92% inhibition at 10 nM, respectively. The docking of synthesized target compounds for nine protein kinases contained in the Protein Data Bank (PDB) database was carried out. The molecular modeling results for analogue 10 showed that the use of the 4-(aminomethyl)benzamide as a flexible linker leads to a favorable overall geometry of the molecule, which allows one to bypass the bulk isoleucine residue and provides the necessary binding to the active center of the T315I-mutant Abl (PDB: 3QRJ).

PROCESS FOR THE PREPARATION OF SUBSTITUTED PYRIMIDINES

This invention relates to an improved process of making compounds of Formula (I) and synthetic intermediates thereof. (I) In particular, the invention relates to an improved process to prepare N-(2-aminophenyl)-4- ((pyrimidin-2-ylamino)methyl)benzamides which requires fewer steps, is efficient, can be used on an industrial scale, and results in a final product which is suitable for pharmaceutical use.

Discovery of N-(2-Aminophenyl)-4-[(4-pyridin-3-ylpyrimidin-2-ylamino) methyl]benzamide(MGCD0103), an orally active histone deacetylase inhibitor

The design, synthesis, and biological evaluation of N-(2-aminophenyl)-4- [(4-pyridin-3-ylpyrimidin-2-ylamino)methyl]benzamide 8 (MGCD0103) is described. Compound 8 is an isotype-selective small molecule histone deacetylase (HDAC) inhibitor that selectively inhibits HDACs 1-3 and 11 at submicromolar concentrations in vitro. 8 blocks cancer cell proliferation and induces histone acetylation, p21ciP/waf1 protein expression, cell-cycle arrest, and apoptosis. 8 is orally bioavailable, has significant antitumor activity in vivo, has entered clinical trials, and shows promise as an anticancer drug.