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【结 构 式】

【分子编号】56983

【品名】3-[1,1'-biphenyl]-4-yl-4-{2-[(6-bromohexyl)oxy]phenyl}-5-methyl-4H-1,2,4-triazole; 2-(3-[1,1'-biphenyl]-4-yl-5-methyl-4H-1,2,4-triazol-4-yl)phenyl 6-bromohexyl ether

【CA登记号】

【 分 子 式 】C27H28BrN3O

【 分 子 量 】490.44294

【元素组成】C 66.12% H 5.75% Br 16.29% N 8.57% O 3.26%

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:(X)

Acetylation of o-aminophenol (I) gives o-hydroxy acetanilide (II), which is then protected as the benzyl ether (III) with benzyl bromide and K2CO3. Treatment of acetamide (III) with P2S5 affords the corresponding thioamide (IV), and subsequent S-methylation of (IV) gives rise to the thioimidate (V). Cyclization of thioimidate (V) with 4-biphenylcarboxylic acid hydrazide (VI) in hot DMF leads to the triazole derivative (VII). After benzyl group hydrogenolysis in (VII), the resultant phenol (VIII) is alkylated with 1,6-dibromohexane (IX) to produce the bromohexyl ether (X). Finally, condensation of bromide (X) with N-methylpiperazine (XI) furnishes the title compound.

1 Kakefuda, A.; et al.; Synthesis and pharmacological evaluation of 5-(4-biphenyl)-3-methyl-4-phenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human vasopressin V1A receptor. J Med Chem 2002, 45, 12, 2589.
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) 18663 o-aminophenol; 2-aminophenol 95-55-6 C6H7NO 详情 详情
(II) 56976 2-Acetamidophenol; 2-Hydroxyacetanilide; o-Acetamidophenol; o-Hydroxyacetanilide 614-80-2 C8H9NO2 详情 详情
(III) 56977 N-[2-(benzyloxy)phenyl]acetamide C15H15NO2 详情 详情
(IV) 56978 N-[2-(benzyloxy)phenyl]ethanethioamide C15H15NOS 详情 详情
(V) 56979 methyl N-[2-(benzyloxy)phenyl]ethanimidothioate C16H17NOS 详情 详情
(VI) 56980 4-Biphenylcarboxylic acid hydrazide; 4-Phenylbenzhydrazide 18622-23-6 C13H12N2O 详情 详情
(VII) 56981 benzyl 2-(3-[1,1'-biphenyl]-4-yl-5-methyl-4H-1,2,4-triazol-4-yl)phenyl ether; 4-[2-(benzyloxy)phenyl]-3-[1,1'-biphenyl]-4-yl-5-methyl-4H-1,2,4-triazole C28H23N3O 详情 详情
(VIII) 56982 2-(3-[1,1'-biphenyl]-4-yl-5-methyl-4H-1,2,4-triazol-4-yl)phenol C21H17N3O 详情 详情
(IX) 24786 1,6-dibromohexane 629-03-8 C6H12Br2 详情 详情
(X) 56983 3-[1,1'-biphenyl]-4-yl-4-{2-[(6-bromohexyl)oxy]phenyl}-5-methyl-4H-1,2,4-triazole; 2-(3-[1,1'-biphenyl]-4-yl-5-methyl-4H-1,2,4-triazol-4-yl)phenyl 6-bromohexyl ether C27H28BrN3O 详情 详情
(XI) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
Extended Information