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Doxefazepam, SAS-643, Doxans

度氟西泮Chemical Name: 7-Chloro-5-(o-fluorophenyl)-1,3-dihydro-3-hydroxy-1-(2-hydroxyethyl)-2H-1,4-benzodiazepin-2-one
CAS No. 40762-15-0
项目整合开发状态: Launched-1984
项目研究机构: Schiapparelli Farmaceutici (Originator)
合成路线: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).
📌 参考资料/链接:
参考文献标题:SAS-643
文献作者:de Angelis,L.; Castar,J.
参考来源:Drugs Fut 1978,3(2),145

📄 详细内容


合成路线: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).

参考文献标题:A new series of benzodiazepines: 1-Hydroxyalkyl derivatives of 1,3-dihydro-2H-1,4-benzodiazepin-2-one
文献作者:Tamagnone,G.F.; et al.
参考来源:Arzneim-Forsch Drug Res 1975,25(5),720-722


合成路线: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).

参考文献标题:Benzodiazepine compounds for therapeutical use
文献作者:De Marchi,F.; Tamagnone,G.F.
参考来源:DE 2338058; ES 405260; FR 2194432; GB 1431282; JP 49080086


合成路线: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).
参考文献标题:A new benzodiazepine: 1-(2-hydroxyethyl)-3-hydroxy-7-chloro-1,3-dihydro-5-(o-fluorophenyl)-2H-1,4-benzodiazepine-2-one
文献作者:Tamagnone,G.F.; et al.
参考来源:J Pharm Pharmacol 1974,26566


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