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【结 构 式】

【分子编号】18186

【品名】2-cyanoethyl 5-(aminocarbonyl)-2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylate

【CA登记号】

【 分 子 式 】C18H18N4O5

【 分 子 量 】370.36488

【元素组成】C 58.37% H 4.9% N 15.13% O 21.6%

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:(IX)

Treatment of a benzenic solution of 4-piperidone hydrate (I) with anhydrous AlCl3 provided 4,4-diphenylpiperidine (II). Then, conjugate addition of acrylonitrile (III) in the presence of triethylamine in ethanol gave the cyanoethylpiperidine (IV), which was reduced with borane in THF to afford the intermediate primary amine (V). Dihydropyridine (IX) was prepared by Hantzsch synthesis by condensation of 3-aminocrotonamide (VI), 4-nitrobenzaldehyde (VII) and cyanoethyl acetoacetate (VIII) in refluxing ethanol. Cyanoethyl ester was then cleaved with dilute KOH at 0 C to give acid (X), which was finally coupled with amine (V) by treatment with DEC to yield the target amide.

1 Cox, E.D.; et al.; Identification of a dihydropyridine as a potent alpha1a adrenoceptor-selective antagonist that inhibits phenylephrine-induced contraction of the human prostate. J Med Chem 1998, 41, 14, 2643.
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) 18178 4,4-piperidinediol 73390-11-1 C5H11NO2 详情 详情
(II) 13154 4,4-Diphenylpiperidine C17H19N 详情 详情
(III) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(IV) 18181 3-(4,4-diphenyl-1-piperidinyl)propanenitrile C20H22N2 详情 详情
(V) 18182 3-(4,4-diphenyl-1-piperidinyl)-1-propanamine; 3-(4,4-diphenyl-1-piperidinyl)propylamine C20H26N2 详情 详情
(VI) 18183 (E)-3-amino-2-butenamide C4H8N2O 详情 详情
(VII) 18184 4-Nitrobenzaldehyde 555-16-8 C7H5NO3 详情 详情
(VIII) 13993 2-cyanoethyl 3-oxobutanoate C7H9NO3 详情 详情
(IX) 18186 2-cyanoethyl 5-(aminocarbonyl)-2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylate C18H18N4O5 详情 详情
(X) 18187 5-(aminocarbonyl)-2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid C15H15N3O5 详情 详情
Extended Information