GW-505524B

Chemical Name: N-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-N-[2-(methylsulfonyl)phenyl]amine
CAS No. 305809-45-4, 305809-46-5 (fumarate salt), 305809-64-7 (monohydrochloride)
项目整合开发状态: Preclinical
项目研究机构: GlaxoSmithKline (Originator)
合成路线:2-(Methylthio)aniline (I) was alkylated with 2-(chloromethyl)-2-imidazoline hydrochloride (II) in phenol at 120 C to afford the condensation product (III).Subsequent oxidation of the thioether functionality of (III) with m-chloroperbenzoic acid gave rise to the target sulfone.

合成路线: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).