N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-5-methoxy-2-(methylsulfanyl)aniline; N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-N-[5-methoxy-2-(methylsulfanyl)phenyl]amine -Drug Synthesis Database

【结构式】

【分子编号】63671

【品名】N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-5-methoxy-2-(methylsulfanyl)aniline; N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-N-[5-methoxy-2-(methylsulfanyl)phenyl]amine

【CA登记号】

【分子式】C₁₂H₁₇N₃OS

【分子量】251.3526

【元素组成】C 57.34% H 6.82% N 16.72% O 6.37% S 12.76%

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：(V)

5-Methoxy-2-methylbenzothiazole (I) is hydrolyzed by NaOH in ethylene glycol to furnish 2-amino-4-methoxythiophenol (II), which is further alkylated with iodomethane and potassium tert-butoxide, yielding thioether (III). Condensation of aniline (III) with 2-(chloromethyl)imidazoline (IV) in the presence of phenol provides (V). After oxidation of sulfide (V) to the corresponding sulfone by means of m-chloroperbenzoic acid, the title compound is isolated as its fumarate salt (1,2).

参考文献中间体

合成目标

【1】 Hodson, S.J.; Bishop, M.J.; Speake, J.D.; Navas, F. III; Garrison, D.T.; Bigham, E.C.; Saussy, D.L. Jr.; Liacos, J.A.; Irving, P. E.; Gobel, M.J.; Sherman, B.W.; 2-(Anilinomethyl)imidazolines as alpha1 adrenergic receptor agonists: The discovery of alpha1a subtype selective 2'-alkylsulfonyl-substituted analogues. J Med Chem 2002, 45, 11, 2229.
【2】 Hodson, S.J.; Navas, F. III; Bishop, M.J.; Bigham, E.C.; Garrison, D.T.; Drewry, D.H.; Speake, J.D. (Glaxo Group Ltd.); Imidazoline derivs. as alpha-1A adrenoceptor ligands. WO 0066563 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	63668	5-methoxy-2-methyl-1,3-benzothiazole; methyl 2-methyl-1,3-benzothiazol-5-yl ether	C₉H₉NOS	详情	详情
(II)	63669	2-amino-4-methoxybenzenethiol; 2-amino-4-methoxyphenylhydrosulfide	C₇H₉NOS	详情	详情
(III)	63670	5-methoxy-2-(methylsulfanyl)aniline; 5-methoxy-2-(methylsulfanyl)phenylamine	C₈H₁₁NOS	详情	详情
(IV)	17330	2-(chloromethyl)-4,5-dihydro-1H-imidazole	C₄H₇ClN₂	详情	详情
(V)	63671	N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-5-methoxy-2-(methylsulfanyl)aniline; N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-N-[5-methoxy-2-(methylsulfanyl)phenyl]amine	C₁₂H₁₇N₃OS	详情	详情

Extended Information