Zonampanel, YM-872

唑南帕奈Chemical Name: 2-[7-(1-Imidazolyl)-6-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl]acetic acid
CAS No. 210245-80-0, 179010-47-0 (monoHCl)
项目整合开发状态: Phase II
项目研究机构: Yamanouchi (Originator)
合成路线:The title compound has been obtained by two related ways: Condensation of glycine ethyl ester (II) with 2,4-difluoronirobenzene (I) provided the N-arylglycine (III),which was further reduced to the phenylenediamine derivative (IV) by catalytic hydrogenation.Acylation of diamine (IV) with ethyl chloroglyoxylate,followed by ring closure in refluxing ethanol,yielded the quinoxalinedione (V).Subsequent electrophyllic nitration of (V) furnished the 6-nitroquinoxaline (VI).The fluoride group of (III) was then displaced with imidazole (VII) in hot DMF yielding the imidazolyl quinoxaline (VIII).Finally,basic hydrolysis of the ethyl ester function of (VIII) gave the target carboxylic acid.

合成路线:In a related procedure,the nitrophenyl imidazole (IX) was reduced to diamine (X) by catalytic hydrogenation.Acylation of diamine (X) with ethyl chloroglyoxylate,followed by ring closure,gave rise to quinoxaline (XI),which was then nitrated to afford (VIII) with fuming nitric acid.Finally,basic hydrolysis of the ethyl ester group of (VIII) as above,yielded the corresponding acid.