合成路线:CD-832.HCl can be obtained by several different ways:1) The cyclization of benzaldehyde (IX) with acetoacetate (V) and crotonate (VII) in refluxing isopropanol gives 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) 5-[2-(3-pyridylcarboxamido)ethyl] diester (X),which by reaction with tetrabutylammonium fluoride in THF/DMF,or with Na2S in dichloromethane/methanol,eliminates vinyl cyanide yielding the dihydropyridine monoester (XI).Finally,this compound is esterified with (XII) by means of acetyl chloride and acetic anhydride in dichloromethan).2) The cyclization of benzaldehyde (IX) with crotonate (VI) and acetoacetate (VIII) as before also gives dihydropyridine (X).3) The reaction of benzaldehyde (IX) with acetoacetate (V) by means of piperidinium acetate in refluxing benzene gives the corresponding 3-nitrobenzylidene derivative (XIII),which is then cyclized with crotonate (VII) to afford the previously obtained dihydropyridine (X).4) The reaction of benzaldehyde (IX) with acetoacetate (V) by means of piperidinium acetate in refluxing benzene gives the 3-nitrobenzylidene derivative (XIII),which is then cyclized with 3-aminocrotonic acid ester (XIV) in refluxing isopropanol.
参考文献标题:1,4-Dihydropyridine derivs
文献作者:Ogawa,T.; Ota,T.; Sato,S.; Sunaga,T.; Watanabe,Y.; Hatayama,K.(Taisho Pharmaceutical Co.,Ltd.)
参考来源:EP 0370821; JP 1990223580; US 5047543
合成路线:The starting products are prepared as follows: The reaction of pyridine-3-carboxylic acid methyl ester (I) with ethanolamine (II) gives the 2-hydroxyethylamide (III),which by reaction with diketene in THF yields the corresponding acetoacetic ester (V).The reaction of (V) with ammonia in THF affords the expected 3-aminocrotonate ester (VI).
合成路线:CD-832.HCl can be obtained by several different ways:1) The cyclization of benzaldehyde (IX) with acetoacetate (V) and crotonate (VII) in refluxing isopropanol gives 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) 5-[2-(3-pyridylcarboxamido)ethyl] diester (X),which by reaction with tetrabutylammonium fluoride in THF/DMF,or with Na2S in dichloromethane/methanol,eliminates vinyl cyanide yielding the dihydropyridine monoester (XI).Finally,this compound is esterified with (XII) by means of acetyl chloride and acetic anhydride in dichloromethan).2) The cyclization of benzaldehyde (IX) with crotonate (VI) and acetoacetate (VIII) as before also gives dihydropyridine (X).3) The reaction of benzaldehyde (IX) with acetoacetate (V) by means of piperidinium acetate in refluxing benzene gives the corresponding 3-nitrobenzylidene derivative (XIII),which is then cyclized with crotonate (VII) to afford the previously obtained dihydropyridine (X).4) The reaction of benzaldehyde (IX) with acetoacetate (V) by means of piperidinium acetate in refluxing benzene gives the 3-nitrobenzylidene derivative (XIII),which is then cyclized with 3-aminocrotonic acid ester (XIV) in refluxing isopropanol.
参考文献标题:CD-832.HCl
文献作者:Mealy,N.; Martel,A.M.; Castar,J.
参考来源:Drugs Fut 1996,21(12),1221
合成路线:The starting products are prepared as follows: The reaction of pyridine-3-carboxylic acid methyl ester (I) with ethanolamine (II) gives the 2-hydroxyethylamide (III),which by reaction with diketene in THF yields the corresponding acetoacetic ester (V).The reaction of (V) with ammonia in THF affords the expected 3-aminocrotonate ester (VI).
合成路线:CD-832.HCl can be obtained by several different ways:1) The cyclization of benzaldehyde (IX) with acetoacetate (V) and crotonate (VII) in refluxing isopropanol gives 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) 5-[2-(3-pyridylcarboxamido)ethyl] diester (X),which by reaction with tetrabutylammonium fluoride in THF/DMF,or with Na2S in dichloromethane/methanol,eliminates vinyl cyanide yielding the dihydropyridine monoester (XI).Finally,this compound is esterified with (XII) by means of acetyl chloride and acetic anhydride in dichloromethan).2) The cyclization of benzaldehyde (IX) with crotonate (VI) and acetoacetate (VIII) as before also gives dihydropyridine (X).3) The reaction of benzaldehyde (IX) with acetoacetate (V) by means of piperidinium acetate in refluxing benzene gives the corresponding 3-nitrobenzylidene derivative (XIII),which is then cyclized with crotonate (VII) to afford the previously obtained dihydropyridine (X).4) The reaction of benzaldehyde (IX) with acetoacetate (V) by means of piperidinium acetate in refluxing benzene gives the 3-nitrobenzylidene derivative (XIII),which is then cyclized with 3-aminocrotonic acid ester (XIV) in refluxing isopropanol.
参考文献标题: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
文献作者:Ogawa,T.; Hatayama,K.; Maeda,H.; Kita,Y.
参考来源:Chem Pharm Bull 1994,42(8),1579-89
产品链接: CAS No. 129904-55-8››