96382-71-7

Basic information

• Product Name: DEHYDRO FELODIPINE-13C4
• Synonyms: DEHYDRO FELODIPINE-13C4;4-(2,3-Dichlorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Ethyl Methyl Ester;H 152/3;H 152/37;4-(2,3-Dichlorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid 5-ethyl 3-methyl ester;4-(2,3-Dichlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid 3-ethyl 5-methyl ester;Felodipine EP IMpurity A;3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
• CAS NO: 96382-71-7
• Molecular Formula: C₁₈H₁₇Cl₂NO₄
• Molecular Weight: 382.241
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 96382-71-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 70-73C
• Boiling Point: 444.8°Cat760mmHg
• Flash Point: 222.8°C
• Appearance: /
• Density: 1.288g/cm³
• Vapor Pressure: 4.16E-08mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: DEHYDRO FELODIPINE-13C4(CAS DataBase Reference)
• NIST Chemistry Reference: DEHYDRO FELODIPINE-13C4(96382-71-7)
• EPA Substance Registry System: DEHYDRO FELODIPINE-13C4(96382-71-7)

Safety Data

• Hazardous Substances Data: 96382-71-7(Hazardous Substances Data)

Usage

Description

DEHYDRO FELODIPINE-13C4 is a stable isotope-labeled compound derived from Dehydro Felodipine, which is the primary metabolite of Felodipine. It is a white to off-white solid and is used for various applications in different industries.
Used in Pharmaceutical Industry:
DEHYDRO FELODIPINE-13C4 is used as a reference material for the identification and quantification of Dehydro Felodipine in pharmaceutical formulations and biological samples. Its stable isotope labeling allows for accurate and sensitive detection using mass spectrometry techniques.
Used in Drug Metabolism Studies:
DEHYDRO FELODIPINE-13C4 is used as a tracer compound in drug metabolism studies to investigate the metabolic pathways and enzyme interactions of Felodipine and its metabolites. This helps in understanding the pharmacokinetics and pharmacodynamics of the drug, as well as its potential drug-drug interactions.
Used in Quality Control:
DEHYDRO FELODIPINE-13C4 is used as a quality control standard for the assessment of analytical methods and instruments used in the analysis of Felodipine and its impurities. Its stable isotope labeling ensures accurate quantification and reliable results in quality control processes.
Used in Environmental Analysis:
DEHYDRO FELODIPINE-13C4 can be used as a tracer compound in environmental analysis to study the fate and transport of Felodipine and its metabolites in various environmental matrices, such as water, soil, and air. This helps in understanding the environmental impact of the drug and its metabolites.
Used in Forensic Analysis:
DEHYDRO FELODIPINE-13C4 can be used as a reference compound in forensic analysis to detect and quantify Felodipine and its metabolites in biological samples, such as blood, urine, and tissues. This aids in investigations related to drug abuse, overdose, or poisoning cases.

InChI:InChI=1/C18H17Cl2NO4/c1-5-25-18(23)14-10(3)21-9(2)13(17(22)24-4)15(14)11-7-6-8-12(19)16(11)20/h6-8H,5H2,1-4H3

Synthetic route

ethyl 2-(2,3-dichlorobenzylidene)-3-oxobutanoate (94739-24-9) + methyl 3-aminocrotonate (14205-39-1) → Dehydrofelodipine (96382-71-7)

Conditions	Yield
In ethanol at 50 - 55℃; for 8h; Darkness; Large scale;	90%

ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate (72509-76-3) → Dehydrofelodipine (96382-71-7)

Conditions	Yield
With potassium carbonate; eosin Y bis(tetrabutyl ammonium salt) In methanol; water at 20℃; for 12h; Irradiation; Green chemistry;	83%
With potassium carbonate In ethanol; water at 20℃; for 12h;	83.1%
Stage #1: ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate With hydrogenchloride In water Stage #2: With nickel In water at 20℃; for 4h;	72.4%
With potassium phosphate; ethylenediaminetetraacetic acid; Emulgen 911; human liver cytochrome b5; human liver HL 39 lipid extract; rabbit liver NADPH-P-450 reductase; yeast P-450 IIIA4; magnesium chloride In water Rate constant; other human liver enzymes;

ethyl acetoacetate (141-97-9) + acetoacetic acid methyl ester (105-45-3) + 2,3-dichlorobenzylaldehyde (6334-18-5) → Dehydrofelodipine (96382-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium acetate / ethanol / 2 h / 80 °C 2: eosin Y bis(tetrabutyl ammonium salt); potassium carbonate / water; methanol / 12 h / 20 °C / Irradiation; Green chemistry View Scheme

ethyl acetoacetate (141-97-9) + 2,3-dichlorobenzylaldehyde (6334-18-5) → Dehydrofelodipine (96382-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: piperidine; acetic acid / 6 h / 15 - 55 °C / Large scale 2: ethanol / 8 h / 50 - 55 °C / Darkness; Large scale View Scheme

Upstream product

• 72509-76-3 ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 94739-24-9 ethyl 2-(2,3-dichlorobenzylidene)-3-oxobutanoate 
• 14205-39-1 methyl 3-aminocrotonate 

Relevant articles and documents

Dihydropyridine compound dehydrogenation aromatization method and in use in the drug detection (by machine translation)

Relates to dihydropyridine compound dehydrogenation aromatization method and in use in the drug detection, compounds such as nifedipine, amlodipine, Cini horizontal, Lacidipine, felodipine, NIKA of amlodipine, nitrendipine, nimodipine and BANI to equal, the method in acidic aqueous solution in the presence of a nickel-containing catalyst in the oxidation reaction of the then purified to realize. The method can be used for preparing this kind of drug detection and quality monitoring of the impurity reference substance, also can be used for quality detection process is used in the instrument of the instrument such as the dissolution of the design reference, drug synthesis process and the design of the manufacturing process of the preparation of the reference, in order to avoid impurities introduced by the process channels, in addition can also be dihydropyridine compound of related synthetic process route provides design provides a reference. The reaction can be in the acidic aqueous solution, to a suitable oxidant (such as air) as the oxidizing agent, in the presence of nickel, at normal temperature to carry out dehydrogenation aromatization reaction, mild reaction conditions, the target compound of high conversion rate, the operation is simple, by-product little small pollution to the environment, is a completely environment-friendly preparation process. (by machine translation)

For 1, 4 - dihydro pyridine compound to prepare the corresponding pyridine compound (by machine translation)

The invention discloses a method for the 1, 4 - dihydro pyridine compound to prepare the corresponding pyridine compound. The method of the invention is: will be 1, 4 - dihydro pyridine compound, eosin Y of the four n-butyl ammonium salt, potassium carbonate is added to the organic solvent with the water in the mixed solvent of stirring and mixing, inject the air in visible light irradiation under the conditions of reaction, to be after the reaction, by adding ethyl acetate, respectively water, saturated ammonium chloride washing, removal of inorganic alkali and adjust the system to subacid, in the organic phase by adding a small amount of activated carbon to remove the pigment, then dried with anhydrous sodium sulfate, turns on lathe does, recrystallize and obtain the corresponding pyridine compound. The method of the invention compared with the prior art has to oxygen in air as the oxidizing agent, is cheap and easy to get; to sunlight as the energy source, so that the industrial production more favorable; catalytic amount of the use of non-metal catalyst, reduces the cost of synthesizing, avoiding the noble metal in the accumulation of drug in the synthesis. (by machine translation)

Pyridyl compounds and pharmaceutical compositions containing them

The present invention is concerned with new pyridine double esters of formula (I), their acids, and pharmaceutically acceptable salts. These compounds can be obtained by oxydation of the corresponding 1,4-dihydropyridines, and they are useful as cardioprotective agents in pharmaceutical compositions.