2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole; 2-(2-chloro-1H-benzimidazol-1-yl)ethyl ethyl ether -Drug Synthesis Database

【结构式】

【分子编号】20902

【品名】2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole; 2-(2-chloro-1H-benzimidazol-1-yl)ethyl ethyl ether

【CA登记号】

【分子式】C₁₁H₁₃ClN₂O

【分子量】224.6898

【元素组成】C 58.8% H 5.83% Cl 15.78% N 12.47% O 7.12%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VI)

A new synthesis of KB-2413 has been described: The reaction of 2-chloronitrobenzene (I) with 2-ethoxyethylamine (II) gives 1-(2-ethoxyethylamino)-2-nitrobenzene (III), which is reduced with Zn and NaOH to N-(2-ethoxyethyl-o-phenylenediamine (IV). The cyclization of (IV) with urea in amyl alcohol affords 1-(2-ethoxyethyl)benzimidazol-2-one (V), which is treated with refluxing POCl3 yielding 2-chloro-1-(2-ethoxyethyl)benzimidazole (VI). Finally, this compound is condensed with N-methylhexahydro-1,4-diazepine (VII) and treated with fumaric acid.

参考文献中间体

合成目标

【1】 Awata, N.; Satomi, O.; Synthesis of 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)-[2-14C]benzimidazole difumarate ([14C]KB-2413). J Label Compd Radiopharm 1987, 24, 3, 331-8.

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)	15248	1-chloro-2-nitrobenzene	88-73-3	C₆H₄ClNO₂	详情	详情
(II)	20898	2-ethoxyethylamine; 2-ethoxy-1-ethanamine	110-76-9	C₄H₁₁NO	详情	详情
(III)	20899	N-(2-ethoxyethyl)-N-(2-nitrophenyl)amine; N-(2-ethoxyethyl)-2-nitroaniline		C₁₀H₁₄N₂O₃	详情	详情
(IV)	20900	N(1)-(2-ethoxyethyl)-1,2-benzenediamine; N-(2-aminophenyl)-N-(2-ethoxyethyl)amine		C₁₀H₁₆N₂O	详情	详情
(V)	20901	1-(2-ethoxyethyl)-1,3-dihydro-2H-benzimidazol-2-one		C₁₁H₁₄N₂O₂	详情	详情
(VI)	20902	2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole; 2-(2-chloro-1H-benzimidazol-1-yl)ethyl ethyl ether		C₁₁H₁₃ClN₂O	详情	详情
(VII)	20903	1-methyl-1,4-diazepane	4318-37-0	C₆H₁₄N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The reaction of 2-chlorobenzimidazole (I) with 2-chloroethyl ethyl ether (II) by means of NaOH in DMF gives 1-(2-ethoxyethyl)benzimidazole (III), which is then condensed with N-methylhomopiperazine (IV) at 120 C.

参考文献中间体

合成目标

【1】 Iemura, R.; et al. (Kanebo Pharmaceuticals, Ltd.); Benzimidazole derivatives, process for the peparation thereof and pharmaceutical composition containing the same. EP 0079545; JP 58079983 .
【2】 Serradell, M.N.; Castaner, J.; KB-2413. Drugs Fut 1985, 10, 5, 397.

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)	26761	2-chloroimidazo[1,2-a]pyridine; 2-chlorobenzimidazole; 2-Amino-4'-chlorodiphenylether; 2-Aminodiphenylether; 2-chloro-1H-benzimidazole	4857-06-1	C₇H₅ClN₂	详情	详情
(II)	29358	1-chloro-2-ethoxyethane	628-34-2	C₄H₉ClO	详情	详情
(III)	20902	2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole; 2-(2-chloro-1H-benzimidazol-1-yl)ethyl ethyl ether		C₁₁H₁₃ClN₂O	详情	详情
(IV)	20903	1-methyl-1,4-diazepane	4318-37-0	C₆H₁₄N₂	详情	详情

Extended Information