SN-22977, NSC-683247, AMAC

Chemical Name: 9-Amino-N-[2-(dimethylamino)ethyl]-5-methylacridine-4-carboxamide
项目整合开发状态: Biological Testing
项目研究机构: University of Auckland (Originator)
合成路线:The intermediate 6-methyldiphenylamine-2,2'-dicarboxylic acid (V) has been synthesized in two similar ways.1.By Jourdan-Ullman copper-catalyzed condensation of 6-methylbenzoic acid (I) with 2-aminobenzoic acid (II); and2.By the same type of condensation,but using 2-amino-3-methylbenzoic acid (III) and 2-chlorobenzoic acid (IV).The cyclization of the intermediate dicarboxylic acid (V) under acidic conditions gives 5-methyl-9-oxo-9,10-dihydroacridine-4-carboxylic acid (VI),which is treated with hot SOCl2 and DMF to yield 9-choloro-5-methylacridine-4-carbonyl chloride (VII).The reaction of (VII) with N,N-dimethylethylenediamine (VIII) in dichloromethane affords the corresponding amide (IX),which is finally treated first with phenol at 100 C and then with a stream of dry ammonia at 110-20 C to obtain the target 9-aminoacridine derivative.