• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】EPH-350

【化学名称】1-(5-Methylpyridin-2-yl)ethanone (1-methyl-1H-benzimidazol-2-yl)hydrazone

【CA登记号】379226-93-4

【 分 子 式 】C16H17N5

【 分 子 量 】279.34739

【开发单位】Universität Innsbruck (Originator)

【药理作用】Oncolytic Drugs

合成路线1

3-Picoline (I) is oxidized to the corresponding N-oxide (II) by means of peracetic acid. Condensation of (II) with dimethylcarbamoyl chloride furnishes carbamate (III), which is then reacted with cyanotrimethylsilane, producing 2-cyano-5-methylpyridine (IV). Subsequent addition of methylmagnesium iodide to the cyanopyridine (IV) gives rise to the pyridyl ketone (V).

1 Easmon, J.; Fürtinger, S.; Lackner, G. ; Magreiter, E.; Hofmann, J.; Heinisch, G.; Puerstinger, G.; Hydrazones derived from monosubstitued 2-acetylpyridines and 2-hydrazino-1-methylbenzimidazole: Synthesis and biological studies. Eur J Cancer 2002, 38, Suppl. 7.
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) 62792 3-Methylpyridine; 3-Picoline 108-99-6 C6H7N 详情 详情
(II) 62793 3-Methyl-1-pyridiniumolate; 3-Picoline N-oxide 1003-73-2 C6H7NO 详情 详情
(III) 62794 1-{[(dimethylamino)carbonyl]oxy}-3-methylpyridinium chloride C9H13ClN2O2 详情 详情
(IV) 38502 5-methyl-2-pyridinecarbonitrile C7H6N2 详情 详情
(V) 62795 1-(5-methyl-2-pyridinyl)-1-ethanone C8H9NO 详情 详情

合成路线2

Alkylation of 2-chlorobenzimidazole (VI) with iodomethane and NaOH leads to 2-chloro-1-methylbenzimidazole (VII). The 2-chloro group of (VII) is then displaced with hydrazine hydrate to afford hydrazine (VIII). Finally, condensation between ketone (V) and hydrazine (VIII) gives rise to the target hydrazone.

1 Easmon, J.; Fürtinger, S.; Lackner, G. ; Magreiter, E.; Hofmann, J.; Heinisch, G.; Puerstinger, G.; Hydrazones derived from monosubstitued 2-acetylpyridines and 2-hydrazino-1-methylbenzimidazole: Synthesis and biological studies. Eur J Cancer 2002, 38, Suppl. 7.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 62795 1-(5-methyl-2-pyridinyl)-1-ethanone C8H9NO 详情 详情
(VI) 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
(VII) 62796 2-chloro-1-methyl-1H-benzimidazole C8H7ClN2 详情 详情
(VIII) 62797 2-hydrazino-1-methyl-1H-benzimidazole C8H10N4 详情 详情
Extended Information