74936-70-2

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-cyanoethyl 1-methylethyl ester
• Synonyms: 1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid isopropyl 2-cyanoethyl ester;2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-isopropyl ester;2-cyanoethyl isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
• CAS NO: 74936-70-2
• Molecular Formula: C21H23N3O6
• Molecular Weight: 413.43
• Mol File: 74936-70-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 584.1±50.0 °C(Predicted)
• Density: 1.244±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-cyanoethyl 1-methylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-cyanoethyl 1-methylethyl ester(74936-70-2)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-cyanoethyl 1-methylethyl ester(74936-70-2)

Safety Data

• Hazardous Substances Data: 74936-70-2(Hazardous Substances Data)

Upstream product

• 14205-46-0 isopropyl 3-aminocrotonate 
• 99-61-6 3-nitro-benzaldehyde 
• 65193-87-5 2-cyanoethylacetoacetate 
• 143093-33-8 isopropyl β-aminocrotonate 
• 542-08-5 isopropyl acetoacetate 
• 193539-61-6 (Z)-3-Amino-but-2-enoic acid 2-cyano-ethyl ester 
• 39562-25-9 3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester 
• 118431-79-1 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid,1-methylethyl ester 
• 88977-32-6 2-cyanoethyl 3-amino-2-butenoate 

Downstream Products

• 74936-69-9 1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid monoisopropyl ester 

Relevant articles and documents

Compound and its as L-type calcium channel blocker or/and application of acetylcholine esterase inhibitors

Disclosed in this invention are compounds and the uses as L-type calcium channel blocker and/or acetylcholinesterase inhibitor thereof. The uses of said compounds in the manufactures of a medicament for the treatment of cardiovascular diseases, apoplexy or senile dementia are also disclosed in the present invention.

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.

Nimodipine: Synthesis and metabolic pathway

Key step of the synthesis of the calcium antagonistic cerebral vasodilator (±) isopropyl-2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (Bay e 9736, nimodipine) is the cyclising Michael addition. A pharmacokinetic study with 14C-nimodipine in the rat revealed as major metabolites the dihydropyridines as well as the pyridines. A potential metabolic pathway is discussed involving ether cleavage and oxidation to the pyridine form as primary biotransformation steps. Reference metabolites were synthesized using 1,4-dihydropyridines with appropriate functionalities as precursors.