GENZ-29155

Chemical Name: 2-Benzoyl-N-[1-(3-cyanophenyl)-1-[N-(2,2-diphenylethyl)carbamoylmethyl]-N-[2-(1H-imidazol-4-yl)ethyl]benzamide
CAS No. 374080-21-4, 374080-26-9 ((R)-isomer), 374080-27-0 ((S)-isomer)
项目整合开发状态: Discontinued
项目研究机构: Genzyme (Originator)
合成路线:2,2-Diphenylethylamine (I) is converted into the corresponding formamide (II) upon refluxing in ethyl formate.Subsequent dehydration of formamide (II) with phosphorus oxychloride in the presence of diisopropylamine furnishes isocyanide (III)

合成路线:The title compound is prepared according to the Ugi reaction by combination of the four components: isocyanide (III),m-cyanobenzaldehyde (IV),2-benzoylbenzoic acid (V),and histamine (VI) in refluxing MeOH

合成路线:Condensation of the pyridyl enaminone (I) with thiourea (II) in the presence of NaOEt gives 2-mercapto-4-(pyridin-2-yl)pyrimidine (III),which is alkylated with iodomethane,producing the corresponding methylsulfanyl pyrimidine (IV).Subsequent displacement of the methylsulfanyl group of (IV) with hydrazine leads to the hydrazino pyrimidine (V).Rhodium acetate-catalyzed coupling between 3-diazo-2,4-pentanedione (VI) and 4-chlorophenol (VII) furnishes the chlorophenyl ether (VIII).The tile pyrazole derivative is finally obtained by condensation between hydrazine (V) and diketone (VIII) in the presence of p-toluenesulfonic acid in boiling EtOH.