4-[4-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]-1-piperazinyl}ethoxy)phenyl]-1-butanol -Drug Synthesis Database

【结构式】

【分子编号】64425

【品名】4-[4-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]-1-piperazinyl}ethoxy)phenyl]-1-butanol

【CA登记号】

【分子式】C₂₉H₃₅ClN₂O₂

【分子量】479.06188

【元素组成】C 72.71% H 7.36% Cl 7.4% N 5.85% O 6.68%

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：(VIII)

4-Iodophenol (I) is alkylated with 1,2-dibromoethane (II) to afford 1-(2-bromoethoxy)-4-iodobenzene (III). Subsequent palladium-catalyzed coupling of aryl iodide (III) with 3-butyn-1-ol (IV) furnishes the phenylbutynol adduct (V), which is further hydrogenated in the presence of Pd/C to the saturated alcohol (VI). Condensation of the alkyl bromide (VI) with (R)-p-chlorobenzhydrylpiperazine (VII) produces the dialkylated piperazine (VIII). Then, Mitsunobu coupling of arylbutanol (VIII) with phenoxycarbonylaminophenoxyformate (IX) leads to the protected hydroxamic acid (X). This is finally treated with methanolic ammonia to provide the title N-hydroxyurea derivative.

参考文献中间体

合成目标

【1】 Chatelain, P.; Differding, E.; Cai, X.; Hussoin, S.; Grewal, G.; Young, M.; Lewis, T.; Toy-Palmer, A.; Scannel, R.; Ellis, J.; Lassoie, M.-A. (UCB SA); Cpds. and methods for treatment of asthma, allergy and inflammatory disorders. JP 2002540198; US 6451801; WO 0058295 .

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)	22242	4-iodophenol	540-38-5	C₆H₅IO	详情	详情
(II)	10252	1,2-Dibromoethane; Ethylene dibromide	106-93-4	C₂H₄Br₂	详情	详情
(III)	64422	1-(2-bromoethoxy)-4-iodobenzene; 2-bromoethyl 4-iodophenyl ether		C₈H₈BrIO	详情	详情
(IV)	32507	3-butyn-1-ol	927-74-2	C₄H₆O	详情	详情
(V)	64423	4-[4-(2-bromoethoxy)phenyl]-3-butyn-1-ol		C₁₂H₁₃BrO₂	详情	详情
(VI)	64424	4-[4-(2-bromoethoxy)phenyl]-1-butanol		C₁₂H₁₇BrO₂	详情	详情
(VII)	30404	1-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazine		C₁₇H₁₉ClN₂	详情	详情
(VIII)	64425	4-[4-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]-1-piperazinyl}ethoxy)phenyl]-1-butanol		C₂₉H₃₅ClN₂O₂	详情	详情
(IX)	19646	1-[([[(phenoxycarbonyl)oxy]amino]carbonyl)oxy]benzene		C₁₄H₁₁NO₅	详情	详情
(X)	64426	1-[(R)-(4-chlorophenyl)(phenyl)methyl]-4-{2-[4-(4-{(phenoxycarbonyl)[(phenoxycarbonyl)oxy]amino}butyl)phenoxy]ethyl}piperazine		C₄₃H₄₄ClN₃O₆	详情	详情

Extended Information