1-[6-(4-nitrobenzoyl)-1,3-benzodioxol-5-yl]acetone -Drug Synthesis Database

【结构式】

【分子编号】35397

【品名】1-[6-(4-nitrobenzoyl)-1,3-benzodioxol-5-yl]acetone

【CA登记号】

【分子式】C₁₇H₁₃NO₆

【分子量】327.29336

【元素组成】C 62.39% H 4% N 4.28% O 29.33%

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 cyclization of benzophenone (I) with hydrazine in isopropanol gives 8-methyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (II), which is treated with KCN in AcOH at 70 C in a sealed tube to afford nitrile (III). Subsequent treatment of (III) with acetyl chloride gave the N-acetyl benzodiazepine (IV). Finally, the nitro group of (IV) was reduced to the target amine by transfer hydrogenation using hydrazine and Pd/C.

参考文献中间体

合成目标

【1】 Andrási, F.; Balogh, T.; Botka, P.; Elekes, I.; Goldschmidt, K.; Hámori, T.; Korosi, J.; Láng, T.; Moravcsik, I.; Sineger, E.; Somogyi, G.; Zolyomi, G. (Egis Pharmaceuticals Ltd.); 5H-2,3-Benzodiazepine derivs., process for their preparation and pharmaceutical compsns. which contain them. FR 2566774; HU 191702 .
【2】 8-Substd.-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine derivs., as AMPA/kainate receptor inhibitors. EP 1003749; WO 9907707 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情
(I)	35397	1-[6-(4-nitrobenzoyl)-1,3-benzodioxol-5-yl]acetone		C₁₇H₁₃NO₆	详情	详情
(II)	29266	8-methyl-5-(4-nitrophenyl)-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepine		C₁₇H₁₃N₃O₄	详情	详情
(III)	35398	8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-[1,3]dioxolo[4,5-h][2,3]benzodiazepine-8-carbonitrile		C₁₈H₁₄N₄O₄	详情	详情
(IV)	35399	7-acetyl-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-[1,3]dioxolo[4,5-h][2,3]benzodiazepine-8-carbonitrile		C₂₀H₁₆N₄O₅	详情	详情

Extended Information