167963-66-8

Upstream product

• 88488-47-5 2-bromoethyl acetoacetate 
• 129094-89-9 2-(acetylthio)ethyl acetoacetate 
• 129094-92-4 2-acetylthioethyl 2-(3-nitrobenzilidene)acetoacetate 
• 99-61-6 3-nitro-benzaldehyde 
• 167963-68-0 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-acetylsulfanyl-ethyl) ester 5-(2-cyano-ethyl) ester 

Downstream Products

• 121138-49-6 2-cyanoethyl N-trifluoroacetyl-3-piperidinyl-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate N-oxide 
• 121138-48-5 2-cyanoethyl N-trifluoroacetyl-3-piperidinyl-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 121138-42-9 N-benzyl-3-piperidinyl 2-cyanoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 121138-53-2 6-acetoxymethyl-2-methyl-4-(3-nitrophenyl)-5-(3-piperidinyl)oxycarbonyl-3-pyridinecarboxylic acid 
• 121138-39-4 2-cyanoethyl 3-piperidinyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 121138-40-7 2-cyanoethyl 3-piperidinyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 118935-46-9 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-(3-piperidinyl)oxycarbonyl-3-pyridinecarboxylic acid 

Relevant academic research and scientific papers

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.

Synthesis of expected metabolites of benidipine hydrochloride

(±)-(R*)-2,6-Dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5- dicarboxylic acid (R*)-1-benzyl-3-piperidinyl ester, methyl ester hydrochloride (benidipine hydrochloride, KW-3049, 1) a highly potent and long-acting calcium antagonistic 1,4-dihydropyridine derivative, is now under clinical study as an antihypertensive and as an antianginal agent. In order to confirm the structures of the metabolites of KW-3049, 19 compounds were prepared. Among then 11 compounds were found to be metabolites (the compounds 2, 3, 6, 8, 14, 15, 16, 28, 31, 32 and 34) of KW-3049 in rats and/or dogs.