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【结 构 式】

【分子编号】23104

【品名】2-hydroxy-3-nitrobenzaldehyde

【CA登记号】5274-70-4

【 分 子 式 】C7H5NO4

【 分 子 量 】167.12104

【元素组成】C 50.31% H 3.02% N 8.38% O 38.29%

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:(I)

The synthesis of the heteroarylpiperazine part of the molecule begins with 3-nitrosalicylaldehyde (I). Alkylation with diethyl bromomalonate under phase transfer conditions immediately gives the cyclized nitrobenzofuran ethyl ester (II), which is converted to 7-nitrobenzofuran (III) by saponification followed by copper-catalyzed decarboxylation. After chemoselective reduction with hydrazine/Raney Nickel to afford aniline (IV), the benzofuranylpiperazine (V) is obtained by reaction with bis(chloroethyl)amine and isolated as the hydrochloride salt. The benzamide part of befiperide is prepared starting from cumenealdehyde (VI). Permanganate oxidation attords the corresponding carboxylic acid (VII), which is converted to oxazoline (VIII) by a one-pot procedure consisting of consecutive treatment with thionyl chloride, chloroethylamine and sodium hydroxide. Coupling of (V) and (VIII) gives the secondary benzamide (IX), which is converted to befiperide hydrochloride by reaction with potassium tert-butylate, N-methylation of the resulting anion with methyliodide and treatment with hydrochloric acid.

1 Kruse, C.G.; van der Heyden, J.A.M.; Befiperide hydrochloride. Drugs Fut 1988, 13, 11, 939.
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) 23104 2-hydroxy-3-nitrobenzaldehyde 5274-70-4 C7H5NO4 详情 详情
(II) 23105 ethyl 7-nitro-1-benzofuran-2-carboxylate C11H9NO5 详情 详情
(III) 23106 7-nitro-1-benzofuran C8H5NO3 详情 详情
(IV) 23107 1-benzofuran-7-ylamine; 1-benzofuran-7-amine C8H7NO 详情 详情
(V) 23108 1-(1-benzofuran-7-yl)piperazine C12H14N2O 详情 详情
(VI) 23109 4-isopropylbenzaldehyde 122-03-2 C10H12O 详情 详情
(VII) 11698 4-Isopropylbenzoic acid 536-66-3 C10H12O2 详情 详情
(VIII) 23111 2-(4-isopropylphenyl)-4,5-dihydro-1,3-oxazole C12H15NO 详情 详情
(IX) 23112 N-[2-[4-(1-benzofuran-7-yl)-1-piperazinyl]ethyl]-4-isopropylbenzamide C24H29N3O2 详情 详情
Extended Information