2-[3-(acetoxy)-7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]ethyl acetate -Drug Synthesis Database

【结构式】

【分子编号】33461

【品名】2-[3-(acetoxy)-7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]ethyl acetate

【CA登记号】

【分子式】C₂₁H₁₈ClFN₂O₅

【分子量】432.8355032

【元素组成】C 58.27% H 4.19% Cl 8.19% F 4.39% N 6.47% O 18.48%

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)

Compound can be prepared in two similar ways both starting from 7-chloro-1,3-dihydro-5-(o-fluorophenyl)-2H-1,4-benzodiazepin-2-one-4-oxide (I): 1) The condensation of (I) with 2-bromoethanol (A) by means of NaH in DMF gives the N-hydroxyethyl derivative (II), which by refluxing with acetic anhydride is converted into 7-chloro-1,3-dihydro-1-(2-acetoxyethyl)-3-acetoxy-5-(o-fluorophenyl)-2H-1,4-benzodiazepin-2-one (III). Finally, (III) is deacetylated with methanolic ammonia. 2) The condensation of (I) with 2-bromoethylacetate (B) as before gives the N-acetoxyethyl derivative (IV), which by refluxing with acetic anhydride is converted into (III).

参考文献中间体

合成目标

【1】 Tamagnone, G.F.; et al.; A new benzodiazepine: 1-(2-hydroxyethyl)-3-hydroxy-7-chloro-1,3-dihydro-5-(o-fluorophenyl)-2H-1,4-benzodiazepine-2-one. J Pharm Pharmacol 1974, 26, 566.
【2】 De Marchi, F.; Tamagnone, G.F.; Benzodiazepine compounds for therapeutical use. DE 2338058; ES 405260; FR 2194432; GB 1431282; JP 49080086 .
【3】 Tamagnone, G.F.; et al.; A new series of benzodiazepines: 1-Hydroxyalkyl derivatives of 1,3-dihydro-2H-1,4-benzodiazepin-2-one. Arzneim-Forsch Drug Res 1975, 25, 5, 720-722.
【4】 de Angelis, L.; Castaner, J.; SAS-643. Drugs Fut 1978, 3, 2, 145.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	10059	Ethylene bromohydrin; 2-Bromo-1-ethanol	540-51-2	C₂H₅BrO	详情	详情
(B)	33463	2-bromoethyl acetate	927-68-4	C₄H₇BrO₂	详情	详情
(I)	33459	7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate		C₁₅H₁₀ClFN₂O₂	详情	详情
(II)	33460	7-chloro-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate		C₁₇H₁₄ClFN₂O₃	详情	详情
(III)	33461	2-[3-(acetoxy)-7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]ethyl acetate		C₂₁H₁₈ClFN₂O₅	详情	详情
(IV)	33462	1-[2-(acetoxy)ethyl]-7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate		C₁₉H₁₆ClFN₂O₄	详情	详情

Extended Information