SUN-9221

Chemical Name: 1-[4-[4-(4-Fluorobenzoyl)piperidin-1-yl]butyl]-4(E)-(hydroxyimino)-7-methyl-1,4,5,6,7,8-hexahydropyrrolo[2,3-c]azepin-8-one
CAS No. 136976-16-4
项目整合开发状态: Phase I
项目研究机构: Daiichi Suntory Pharma (Originator)
合成路线:2-Pyrrolecarboxylic acid (I) was condensed with ethyl 3-(methylamino)-propionate (II) by means of diethyl phosphorocyanidate to give amide (III).Alkaline hydrolysis of the ethyl ester group of (III) provided carboxylic acid (IV),which was cyclized in 80% polyphosphoric acid at 100 C to afford the pyrroloazepine (V).Subsequent reaction of (V) with 1,4-dichlorobutane (VI) in the presence of K2CO3 yielded the N-(4-chlorobutyl)pyrrole (VII).Treatment of (VII) with hydroxylamine hydrochloride and NaOAc furnished the E-oxime (VIII) as the major isomer.Then,displacement of the chloro atom of (VIII) with 4-(4-fluorobenzoyl)piperidine-HCl (IX) using K2CO3 and NaI yielded the title compound.