2,3-Diaminobenzoic acid (I) is condensed with glycolic acid (II) under acidic conditions to produce 2-(hydroxymethyl)benzimidazole-4-carboxylic acid (III). Chlorination of (III) with SOCl2, followed by acidic hydrolysis of the acid chloride group leads to the chloromethyl benzimidazole (IV). Condensation of chloride (IV) with 1-(2-ethoxyphenyl)piperazine (V) furnishes the disubstituted piperazine (VI). Acid (VI) is finally coupled to 3-aminoquinuclidine (VII) via activation with CDI to produce the title amide. (1-3)
2-(Trichloromethyl)quinazolin-4-one (I) is chlorinated with oxalyl chloride in the presence of DMF producing 4-chloro-2-(trichloromethyl)quinazoline (II). Subsequent coupling of chloroquinazoline (II) with 4-(4'-aminophenylazo)phenylarsonic acid (III) in refluxing isopropanol furnishes the title compound. (1,2)
The title compound is prepared by condensation between 4-chloro-2-(methylthio)pyrimidine (I) and p-arsanilic acid (II) in refluxing alcohol.