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【结 构 式】

【分子编号】10846

【品名】2-(4-Pyridinyl)butanenitrile

【CA登记号】

【 分 子 式 】C9H10N2

【 分 子 量 】146.19188

【元素组成】C 73.94% H 6.89% N 19.16%

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:(III)

1) The reaction of 4-(chloromethyl)pyridine (I) with KCN in refluxing methanol gives 2-(4-pyridyl)acetonitrile (II), which is alkylated with ethyl iodide and sodium hydride in DMF, yielding 2-(4-pyridyl)butyronitrile (III). The condensation of (III) with acrylonitrile (IV) by means of Triton B in tert-butanol affords 2-cyano-2-(4-pyridyl)hexanenitrile (V), which is finally cyclized with concentrated H2SO4 in refluxing acetic acid. 2) The alkylation of 2-(4-pyridyl)acetic acid ethyl ester (VI) with ethyl iodide and potassium tert-butoxide gives 2-(4-pyridyl)butanoic acid ethyl ester (VII), which is condensed with acrylamide (VIII) by means of potassium tert-butoxide, yielding 4-carbamoyl-2-ethyl-2-(4-pyridyl)butanoic acid ethyl ester (IX). Finally, this compound is cyclized in the presence of potassium tert-butoxide. 3) The condensation of ester (VI) with acrylonitrile (IV) in the presence of Triton B gives 4-cyano-2-(4-pyridyl)butanoic acid ethyl ester (X), which is alkylated with ethyl iodide and lithium diisopropylamide yielding 4-cyano-2-ethyl-2-(4-pyridyl)butanoic acid ethyl ester (XI). Finally, this compound is cyclized with concentrated H2SO4 in refluxing acetic acid.

1 Foster, A.B.; Jarman, M.; Taylor, G.N.; Kwan, C.-S. (Institute of Cancer Research); 2,6-Dioxopiperidine derivs., their preparation and pharmaceutical compsns. containing them. EP 0147121; GB 2151226; JP 1986500613; US 5071857; WO 8502618 .
2 Markson, A.J.; Boss, A.M.; Clissold, D.W.; Thickitt, C.P.; Mann, J.; A concise synthesis of racemic pyridoglutethimide and its resolution using chiral stationary phase HPLC. Tetrahedron 1989, 45, 18, 6011.
3 Jarman, M.; Griggs, L.J.; Wilman, D.E.V.; Rowlands, M.G.; Foster, A.B.; Leung, C.-S.; Analogues of 3-ethyl-3-(4-pyridyl)piperidine-2,6-dione as selective inhibitors of aromatase: Derivatives with variable 1-alkyl and 3-alkyl substituents. J Med Chem 1987, 30, 9, 1550.
4 Sampson, P.; Taylor, G.N.; Leung, C.-S.; Rowlands, M.G.; Plevey, R.G.; Jarman, M.; Foster, A.B.; Analogues of animoglutethimide: Selective inhibition of aromatase. J Med Chem 1989, 28, 2, 200.
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) 10844 4-(Chloromethyl)pyridine 10445-91-7 C6H6ClN 详情 详情
(II) 10845 2-(4-Pyridinyl)acetonitrile C7H6N2 详情 详情
(III) 10846 2-(4-Pyridinyl)butanenitrile C9H10N2 详情 详情
(IV) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(V) 10848 2-Ethyl-2-(4-pyridinyl)pentanedinitrile C12H13N3 详情 详情
(VI) 10849 ethyl 2-(4-pyridinyl)acetate; Ethyl 4-pyridylacetate 54401-85-3 C9H11NO2 详情 详情
(VII) 10850 ethyl 2-(4-pyridinyl)butanoate C11H15NO2 详情 详情
(VIII) 10851 Acrylamide 79-06-1 C3H5NO 详情 详情
(IX) 10852 ethyl 5-amino-2-ethyl-5-oxo-2-(4-pyridinyl)pentanoate C14H20N2O3 详情 详情
(X) 10853 ethyl 4-cyano-2-(4-pyridinyl)butanoate C12H14N2O2 详情 详情
(XI) 10854 ethyl 4-cyano-2-ethyl-2-(4-pyridinyl)butanoate C14H18N2O2 详情 详情
Extended Information