43067-01-2

Usage

Uses

Used in Pharmaceutical Manufacturing:
Dimethyl 4-(2-Chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate is used as an impurity in the production of Amlodipine Besilate (A633500). It is important to monitor and control the levels of this impurity to ensure the safety, efficacy, and quality of the final drug product.
Used in Quality Control and Analysis:
In the pharmaceutical industry, Dimethyl 4-(2-Chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate serves as a reference compound for quality control and analytical testing. It helps in the development and validation of analytical methods to detect and quantify impurities in Amlodipine Besilate, thereby maintaining the standards of the drug.
Used in Research and Development:
This impurity also plays a role in research and development, where it can be used to study the effects of impurities on the pharmacological properties of Amlodipine Besilate. Understanding the behavior of impurities like Dimethyl 4-(2-Chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate can contribute to the optimization of manufacturing processes and the improvement of drug formulations.

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 
• 14205-39-1 methyl (E)-3-aminocrotonate 
• 14205-39-1 methyl 3-aminocrotonate 
• 5837-80-9 methyl 2-acetoxy acetate 

Downstream Products

• 110476-93-2 1-{[3,5-Bis(methoxycarbonyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyrid-2-yl]methylthio}-2,3-dihydroxypropane 
• 130160-97-3 2,6-dimethyl-4-(2'-chlorophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester 
• 97744-29-1 Methyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate 
• 128738-14-7 2,6-Bis-benzylsulfanylmethyl-4-(2-chloro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 128738-13-6 4-(2-Chloro-phenyl)-2-(6-hydroxymethyl-pyridin-2-ylmethoxymethyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 128738-07-8 2-(2-Amino-2-methoxycarbonyl-ethylsulfanylmethyl)-4-(2-chloro-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 128738-11-4 4-(2-Chloro-phenyl)-2-(4-cyano-phenoxymethyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 128738-08-9 4-(2-Chloro-phenyl)-2-methyl-6-(pyrimidin-2-ylsulfanylmethyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 128738-06-7 2-Benzylsulfanylmethyl-4-(2-chloro-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 128738-12-5 4-(2-Chloro-phenyl)-2-methyl-6-(pyridin-3-yloxymethyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 128738-10-3 4-(2-Chloro-phenyl)-2-methyl-6-[1,2,4]triazol-1-ylmethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 128738-09-0 4-(2-Chloro-phenyl)-2-imidazol-1-ylmethyl-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 100276-22-0 methyl 4-(2-chlorophenyl)-1,4,5,7-tetrahydro-2-methyl-5-oxofuro[3, 4-b]pyridine-3-carboxylate 
• 120260-21-1 8-(2-Chloro-phenyl)-3H,5H-difuro[3,4-b;3',4'-e]pyridine-1,7-dione 

Relevant academic research and scientific papers

A New Type of Magnetically-Recoverable Heteropolyacid Nanocatalyst Supported on Zirconia-Encapsulated Fe3O4 Nanoparticles as a Stable and Strong Solid Acid for Multicomponent Reactions

Abstract: A novel highly efficient magnetically retrievable catalyst was developed by the immobilization of H3PW12O40 (20–60 wt%) on the surface of zirconia-encapsulated Fe3O4 nanoparticles. The prepared HPW supported on nano-Fe3O4@ZrO2 heterogeneous acid catalyst (or n-Fe3O4@ZrO2/HPW) was fully characterized by several physicochemical techniques such as: Fourier transform infrared spectroscopy (FT-IR), field emission scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The FT-IR spectroscopic data revealed that H3PW12O40 molecules on the nano-Fe3O4@ZrO2 support existed in the Keggin structure. The acidity of the catalyst was measured by the help of a potentiometric titration with n-butylamine. It was surprising that this very strong solid acid catalyst exhibited an excellent acid strength which was as a result of possessing a higher number of surface active sites compared to its homogeneous analogues. The catalytic activity of the as-prepared novel nano-Fe3O4@ZrO2/HPW was explored through the one-pot three-component synthesis of different 3,4-dihydropyrimidin-2(1H)-ones (i.e. Biginelli reaction) and 1,4-dihydropyridines (i.e. Hantzsh reaction) under solvent free condition. The sample of 40 wt% showed higher acidity and activity in the catalytic transformation. After the reaction, the catalyst/product isolation could be easily achieved with an external magnetic field and the catalyst could be easily recycled for at least five times without any decrease in its high catalytic activity. The excellent recyclability was attributed to the strong interaction between the hydroxyl groups of the nano-Fe3O4@ZrO2 support and the HPW species. Graphical Abstract: [Figure not available: see fulltext.].

Novel Magnetically Separable Sulfated Boric Acid Functionalized Nanoparticles for Hantzsch Ester Synthesis

A novel, separable, solid-acid catalyst consisting of sulfated boric acid nanoparticles immobilized on a silica-coated magnetite support was prepared. This catalyst permits the preparation of dihydropyridine derivatives (Hantzsch esters) by condensation of an aldehyde with two equivalents of a β-keto ester in the presence of ammonium acetate. The catalyst can be recovered and recycled.

A Simple and Efficient One-pot Synthesis of 1,4-dihydropyridines Using Nano-WO3-supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent-free Conditions

Nano-tungsten trioxide-supported sulfonic acid (n-WSA) was found to be an effective heterogeneous catalyst for the one-pot reaction of aromatic aldehydes, β-dicarbonyl compounds and ammonium acetate to afford 1,4-dihydropyridine derivatives in good to excellent yields. The other main advantages of the present method are short reaction times, simple workup, ease in purification and environmentally benign methodology. The reaction conditions were optimized employing Response Surface Method technique (Central Composite Design (CCD)) which is economically considerable because of the minimum number of experiments required to evaluate the effects of multiple parameters on the response.

Synthesis, evaluation of pharmacological activity, and molecular docking of 1,4-dihydropyridines as calcium antagonists

1,4-Dihydropyridine (DHP) is an important class of calcium antagonist. It inhibits the influx of extracellular Ca2+ through L-type voltage-dependent calcium channels. Two series of nifedipine analogues were synthesized and evaluated as calcium

Study of temperature dependent three component dynamic covalent assembly VIa Hantzsch reaction catalyzed by dioxido- and oxidoperoxidomolybdenum(VI) complexes under solvent free conditions

Tridentate ONO donor ligands derived from heterocyclic compound 4-acetyl-3-methyl-1-phenyl-2-pyrazoline-5-one (Hap) and aromatic hydrazides {benzoyl hydrazide (Hbhz), isonicotinoyl hydrazide (Hinh), nicotinoyl hydrazide (Hnah) and furoyl hydrazide (Hfah)} react with [MoVIO2(acac)2] (Hacac = acetylacetone) in equimolar ratio in methanol to give dioxidomolybdenum(vi) complexes, [MoO2(ap-bhz)(MeOH)] 1, [MoO2(ap-inh)(MeOH)] 2, [MoO2(ap-nah)(MeOH)] 3 and [MoO2(ap-fah)(MeOH)] 4. Reaction of these ligands with in situ generated oxidoperoxidomolybdenum(vi) precursor results in the formation of oxidoperoxidomolybdenum(vi) complexes, [MoO(O2)(ap-bhz)(MeOH)] 5, MoO(O2)(ap-inh)(MeOH)] 6, MoO(O2)(ap-nah)(MeOH)] 7 and MoO(O2)(ap-fah)(MeOH)] 8. These complexes have been characterized by elemental analysis, spectroscopic techniques (infrared, UV-vis, 1H and 13C NMR) and thermogravemetric analysis. The structures of complexes [MoVIO2(ap-bhz)(H2O)] 1a (water coordinated), [MoVIO2(ap-bhz)(DMSO)] 1b (DMSO coordinated), [MoVIO2(ap-nah)(DMF)] 3a (DMF coordinated), [MoVIO(O2)(ap-bhz)(MeOH)] 5 (methanol coordinated) and [MoVIO(O2)(Hap-nah)(OMe)]·MeOH 7a (methoxy coordinated) have been confirmed by single crystal X-ray studies. X-ray diffraction study also reveals that tridentate ligands bind to the metal center through enolic oxygen (of pyrazolol), azomethine nitrogen and enolic oxygen (of hydrazide) atoms. In complex 7a, pyridinic nitrogen is protonated. These complexes [dioxidomolybdenum(vi) as well as oxidoperoxidomolybdenum(vi)] have been tested as catalysts for temperature dependent one pot three component (methylacetoacetate, benzaldehyde and ammonium acetate) dynamic covalent assembly, via Hantzsch reaction, using 30% H2O2 as a green oxidant under solvent free conditions. Various parameters such as the amount of catalyst, oxidant and temperature of the reaction mixture have been taken into consideration to optimize the reaction conditions. In the Hantzsch reaction, the temperature and oxidant control the conversion and selectivity of the desired product.

Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions

Abstract Synthesis of 1,4-dihydropyridines by three-component condensation reaction of aldehyde, 1,3-dicarbonyl compounds, and ammonium acetate have been found to be efficiently catalyzed by uranyl nitrate hexahydrate [UO2(NO3)2 ·6H2O] at room temperature under ultrasound irradiation. This novel synthetic method offers the advantages of high yields, short reaction times, simplicity, and easy workup compared to the conventional methods reported in the literature.

Alginic acid: A highly efficient renewable and heterogeneous biopolymeric catalyst for one-pot synthesis of the Hantzsch 1,4-dihydropyridines

Alginic acid, a naturally occurring polysaccharide, in its granular form and without any post-modification was found to be an efficient, environmentally benign, easily recoverable and low-cost catalyst for the clean and rapid synthesis of 1,4-dihydropiridine derivatives (DHPs) just based on its polysaccharide architecture. The Hantzsch pseudo-four-component reaction of ethyl or methyl acetoacetate, ammonium acetate and different aldehydes is catalyzed by alginic acid efficiently under mild conditions to afford the desired products in high to quantitative yields and clean reaction profiles. Avoiding the use of any transition metal, the use of a one-pot and multi-component procedure for the synthesis of DHPs, the reusability of the catalyst and operational simplicity are important features of this methodology.

A magnetic particle-supported sulfonic acid catalyst: Tuning catalytic activity between homogeneous and heterogeneous catalysis

Surface functionalization of magnetic particles is an elegant way to bridge the gap between heterogeneous and homogeneous catalysis. The introduction of magnetic particles (MPs) in a variety of solid matrices allows the combination of well-known procedures for catalyst heterogenization with techniques for magnetic separation. We have conveniently loaded sulfonic acid groups on magnetic particles supports in which chlorosulfonic acid is used as sulfonating agent. The main targets are room temperature, solvent-free conditions, rapid (immediately) and easy immobilization technique, and low cost precursors for the preparation of highly active and stable MPs with high densities of functional groups. The inorganic, magnetic, solid acid catalyst was characterized via Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), transmission electron microscopy (TEM), dynamic light scattering (DLS), vibrating sample magnetometer (VSM) and titration. The catalyst is active for the Hantzsch reaction and the products are isolated in high to excellent yields (90-98%). Supporting this acid catalyst on magnetic particles offers a simple and non-energy-intensive method for recovery and reuse of the catalyst by applying an external magnet. Isolated catalysts were reused for new rounds of reactions without significant loss of their catalytic activity. Copyright

Hantzsch reaction on free nano-Fe2O3 catalyst: Excellent reactivity combined with facile catalyst recovery and recyclability

A magnetic nanoparticle catalyst was readily prepared from inexpensive starting materials which catalyzed the Hantzsch reaction. High catalytic activity and ease of recovery from the reaction mixture using an external magnet, and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system.