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【结 构 式】

【分子编号】25445

【品名】2-cyanoethyl 2,6-dimethyl-5-[(methylamino)carbonyl]-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylate

【CA登记号】

【 分 子 式 】C19H20N4O5

【 分 子 量 】384.39176

【元素组成】C 59.37% H 5.24% N 14.58% O 20.81%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

Condensation of 4-nitrobenzaldehyde (I) with N-methyl acetoacetamide (II) in the presence of piperidine acetate gave benzylideneacetoacetamide (III). This was further condensed with 2-cyanoethyl 3-amino-2-butenoate (IV) to provide dihydropyridine (V), which was resolved into the enantiomers using chiral HPLC. Then, basic hydrolysis of the cyanoethyl ester from the appropriate enantiomer of (V) yielded carboxylic acid (VI). The aminopropyl piperidine (X) was obtained by esterification of 4-phenyl-4-piperidinecarboxylic acid (VII) with MeOH and H2SO4, followed by alkylation of piperidine (VIII) with 3-bromopropylamine (IX). Finally, amine (X) was coupled to acid (VI) by means of EDC and DMAP to furnish the target compound.

1 Nagarathnam, D.; Wetzel, J.M.; Miao, S.W.; Marzabadi, M.R.; Chiu, G.; Wong, W.C.; Hong, X.; Fang, J.; Forray, C.; Branchek, T.A.; Heydorn, W.E.; Chang, R.S.; Broten, T.; Schorn, T.W.; Gluchowski, C.; Design and synthesis of novel alpha1a adrenoceptor-selective dihydropyridine antagonists for the treatment of benign prostatic hyperplasia. J Med Chem 1998, 41, 26, 5320.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18184 4-Nitrobenzaldehyde 555-16-8 C7H5NO3 详情 详情
(II) 25443 N-methyl-3-oxobutanamide 20306-75-6 C5H9NO2 详情 详情
(III) 25444 (Z)-2-acetyl-N-methyl-3-(4-nitrophenyl)-2-propenamide C12H12N2O4 详情 详情
(IV) 13987 2-cyanoethyl (E)-3-amino-2-butenoate C7H10N2O2 详情 详情
(V) 25445 2-cyanoethyl 2,6-dimethyl-5-[(methylamino)carbonyl]-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylate C19H20N4O5 详情 详情
(VI) 25446 2,6-dimethyl-5-[(methylamino)carbonyl]-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid C16H17N3O5 详情 详情
(VII) 25447 4-phenyl-4-piperidinecarboxylic acid 3627-45-0 C12H15NO2 详情 详情
(VIII) 25448 methyl 4-phenyl-4-piperidinecarboxylate C13H17NO2 详情 详情
(IX) 25449 3-bromo-1-propanamine; 3-bromopropylamine 18370-81-5 C3H8BrN 详情 详情
(X) 25450 methyl 1-(3-aminopropyl)-4-phenyl-4-piperidinecarboxylate C16H24N2O2 详情 详情
Extended Information