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 -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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