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Dapiprazole hydrochloride, AF-2139, Remydrial, Rev-Eyes, Reversil, Glamidolo

盐酸达哌唑 达哌唑 Chemical Name: 5,6,7,8-Tetrahydro-3-[2-(4-o-tolyl-1-piperazinyl)-ethyl]-s-triazolo[4,3-a]pyridine monohydrochloride
CAS No. 72822-13-0, 72822-12-9 (free base)
项目整合开发状态: Launched-1986
项目研究机构: Angelini (Originator)
合成路线:By cyclization of O-methylvalerolactam (I) with 3-(4-o-tolyl-1-piperazinyl) propionic acid hydrazide (II) in refluxing xylene,followed by a treatment with ethanolic HCl.
📌 参考资料/链接:
参考文献标题:Cycloalkyltriazoles and process for obtaining same
文献作者:Silvestrini,B.; Baiocchi,L.(ACRAF SpA)
参考来源:FR 2423221; GB 2020269; JP 54157576; NL 7902489; US 4252721

📄 详细内容


合成路线:By cyclization of O-methylvalerolactam (I) with 3-(4-o-tolyl-1-piperazinyl) propionic acid hydrazide (II) in refluxing xylene,followed by a treatment with ethanolic HCl.

参考文献标题:Cycloalkyltriazoles et leur proc閐?de pr閜aration
文献作者:Silvestrini,B.; Baiocchi,L.(ACRAF SpA)
参考来源:BE 0877161


合成路线:By cyclization of O-methylvalerolactam (I) with 3-(4-o-tolyl-1-piperazinyl) propionic acid hydrazide (II) in refluxing xylene,followed by a treatment with ethanolic HCl.

合成路线:Acylation of (1-methylcyclopropyl)guanidine (IV) with 3-bromo-5-chlorothiophene-2-sulfonyl chloride (III) under Schotten-Baumann conditions afforded the sulfonyl guanidine (V).This was cyclized to the desired thienothiadiazine upon treatment with Cs2CO3 and Cu2O in boiling butanol.

合成路线:In a closely related method,guanidine (IV) was sulfonylated with 3,5-dichlorothiophene-2-sulfonyl chloride (VI),and the resultant sulfonylguanidine (VII) was then cyclized in the presence of Cs2CO3 and Cu2O as above.

合成路线:In a different method,(1-methylcyclopropyl)guanidine (I) is acylated by 3-bromo-5-chlorothiophene-2-sulfonyl chloride (II) to produce the sulfonyl guanidine (III).Intramolecular cyclization of (III) in the presence of Cu2O and Cs2CO3 leads to the title thienothiadiazine derivative.Similarly,acylation of guanidine (I) with 3,5-dichlorothiophene-2-sulfonyl chloride (IV) provides sulfonyl guanidine (V),which is then cyclized in the presence of Cu2O and Cs2CO3.

合成路线:In an alternative method,sulfonylation of N-isopropylguanidine (V) with 2,5-dichlorothiophene-3-sulfonyl chloride (IV) produced the sulfonyl guanidine (VI).This was then cyclized to the title compound by treatment with copper bronze and potassium carbonate in boiling DMF.

参考文献标题:Novel process
文献作者:Nielsen,F.E.; Ebdrup,S.(Novo Nordisk A/S)
参考来源:WO 0102410


合成路线:By cyclization of O-methylvalerolactam (I) with 3-(4-o-tolyl-1-piperazinyl) propionic acid hydrazide (II) in refluxing xylene,followed by a treatment with ethanolic HCl.
参考文献标题:
文献作者:
参考来源:Drug Data Rep 1982,465


产品链接: CAS No. 72822-13-0››

产品链接: CAS No.72822-12-9››