110962-94-2

Basic information

• Product Name: 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-methyl ester
• Synonyms: 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-methyl ester;3-(2-cyanoethyl) 5-Methyl 4-(2',3'-dichlorophenyl)-2,6-diMethyl-1,4-dihydropyridine-3,5-dicarboxylate;Clevidipine Butyrate iMpurity Ⅵ;4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-diMethyl-3,5-Pyridinedicarboxylic acid 3-(2-cyanoethyl) 5-Methyl ester;Amlodipine Related Impurity 8;Cleviprex Impurity G;Amlodipine Impurity 8;Clevidipine Butyrate impurity G
• CAS NO: 110962-94-2
• Molecular Formula: C₁₉H₁₈Cl₂N₂O₄
• Molecular Weight: 409.26322
• EINECS: 1312995-182-4
• Product Categories: Clevidipine Butyrate impurity
• Mol File: 110962-94-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 552.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.317±0.06 g/cm3(Predicted)
• PKA: 2.54±0.70(Predicted)
• CAS DataBase Reference: 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-methyl ester(110962-94-2)
• EPA Substance Registry System: 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-methyl ester(110962-94-2)

Safety Data

• Hazardous Substances Data: 110962-94-2(Hazardous Substances Data)

Usage

Uses

4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-Pyridinedicarboxylic Acid 2-cyanoethyl Methyl Ester, is an impurity of Amlodipine (A633495), a dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer.

InChI:InChI=1S/C19H18Cl2N2O4/c1-10-14(18(24)26-3)16(12-6-4-7-13(20)17(12)21)15(11(2)23-10)19(25)27-9-5-8-22/h4,6-7,16,23H,5,9H2,1-3H3

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 65193-87-5 2-cyanoethylacetoacetate 
• 14205-39-1 methyl 3-aminocrotonate 
• 193539-61-6 (Z)-3-Amino-but-2-enoic acid 2-cyano-ethyl ester 
• 74073-22-6 (E/Z)-methyl 2-(2,3-dichlorobenzylidene)acetoacetate 

Downstream Products

• 123853-39-4 (+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid 

Relevant articles and documents

Butyric acid clevidipine preparation method

The invention discloses a preparation method of clevidipine butyrate, comprising the following steps: (1) carrying out one-pot reaction by putting 2,3-dichlorobenzaldehyde, methyl acetoacetate and 3-amino crotonic acid ethyl cyanide in a solvent under the action of a catalyst; (2) carrying out recrystallization to obtain a pure product (+/-)-3-(2-cyanoethyl)-5-methyl-4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid; (3) carrying out a reaction between the pure product and alkali; (4) adding water and hydrochloric acid, and collecting an intermediate from reaction products; and (5) carrying out a reaction between the intermediate and n-chloromethyl butyrate in the presence of an alkaline substance and an iodide catalyst, and finally collecting the target product clevidipine butyrate from reaction products. The preparation method provided by the invention has advantages of high yield, stable product quality and low cost, is simple to operate, and is suitable for industrial product of clevidipine butyrate.

Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetrical 1,4-dihydropyridine dicarboxylates

Several 3-(2-cyanoethyl)-1,4-dihydropyridine carboxylates (16) were prepared in moderate to good yields by means of the Hantzsch reaction. Treatment of these carboxylates with a weak base such as sodium sulfide or tetrabutylammonium fluoride at room temperature afforded smoothly the corresponding 1,4-dihydropyridine monocarboxylic acids (18) in good yields. The monocarboxylic acids 18n and 18o were esterified with 2-nitrooxypropanol or N-(2-hydroxyethyl)nicotinamide p-toluenesulfonic acid salt to afford the selective coronary vasodilators CD-349 (5) and CD-832 (6), respectively.