4-bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzamide -Drug Synthesis Database

【结构式】

【分子编号】45961

【品名】4-bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzamide

【CA登记号】

【分子式】C₁₉H₂₂BrN₃O₂

【分子量】404.3067

【元素组成】C 56.44% H 5.48% Br 19.76% N 10.39% O 7.91%

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)

Coupling of 4-bromobenzoyl chloride (I) with amine (II) by means of Et3N in CH2Cl2 or THF yields bromo derivative (III), which is then converted into boronic acid derivative (IV) by treatment with triisopropyloxyboron and n-BuLi in THF/hexane. Suzuki reaction between (IV) and oxadiazole (V) by means of Pd(PPd3)4 and Na2CO3 in dimethoxyethane (DME)/H2O affords compound (VI), which is finally hydrogenated over Raney-Ni in H2O/MeOH/AcOH to furnish the desired product.

参考文献中间体

合成目标

【1】 März, J.; Cremers, T.; Harting, J.; Liao, Y.; Wikstrom, H.; Rautenberg, W.; Greiner, H.; Sundell, S.; Böttcher, H.; van Amsterdam, C.; New selective and potent 5-HT1B/1D antagonists: Chemistry and pharmacological evaluation of N-piperazinylphenyl biphenylcarboxamides and biphenylsulfonamides. J Med Chem 2000, 43, 3, 517.
【2】 Van Amsterdam, C.; Harting, J.; Wikstrom, H.V.; Liao, Y.; Bottcher, H. (Merck Patent GmbH); Biphenyl derivs.. WO 0005225 .

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)	45960	4-bromobenzoyl chloride	586-75-4	C₇H₄BrClO	详情	详情
(II)	25915	4-methoxy-3-(4-methyl-1-piperazinyl)phenylamine; 4-methoxy-3-(4-methyl-1-piperazinyl)aniline		C₁₂H₁₉N₃O	详情	详情
(III)	45961	4-bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzamide		C₁₉H₂₂BrN₃O₂	详情	详情
(IV)	45964	4-[[4-methoxy-3-(4-methyl-1-piperazinyl)anilino]carbonyl]phenylboronic acid		C₁₉H₂₄BN₃O₄	详情	详情
(V)	45962	3-(4-bromo-3-methylphenyl)-5-methyl-1,2,4-oxadiazole		C₁₀H₉BrN₂O	详情	详情
(VI)	45963			C₂₈H₃₂BrN₅O₃	详情	详情

Extended Information