Tirilazad mesylate, ISV-600, U-74006F, Tridax, Freedox

替拉扎特Chemical Name: 16alpha-Methyl-21-[4-[2,6-bis(pyrrolidino)-4-pyrimidinyl]-1-piperazinyl]pregna-1,4,9(11)triene-3,20-dione monomethanesulfonate hydrate; 21-[4-[2,6-Bis(pyrrolidino)pyrimidin-4-yl]piperazin-1-yl]-16alpha-methyl-pregna-1,4,9(11)-triene-3,20-dione methanesulfonate hydrate
CAS No. 111793-42-1, 110101-67-2 (anhydrous), 110101-66-1 (anhydrous, free base), 111640-96-1 (anhydrous, HCl salt), 111640-95-0 (dimethanesulfonate)
项目整合开发状态: Launched-1995
项目研究机构: Pfizer (Originator)
合成路线:The intermediate pyrimidine (IV) has been obtained as follows: The reaction of 2,4,6-trichloropyrimidine (I) with pyrrolidine in THF gives 6-chloro-2,4-bis(1-pyrrolidinyl) pyrimidine (II),which is condensed with piperazine (III) in pyridine to yield 6-(1-piperazinyl)-2,4-bis(1-pyrrolidinyl)pyrimidine (IV).The methylation of 21-acetoxy-pregna-1,4,9(11),16-tetraene-3,20-dione (V) with methylmagnesium chloride catalyzed by copper propionate,followed by hydrolysis of the acetate group with NaOMe in methanol,gives the 16-alpha-methyl steroid (VI),which is condensed with piperazine intermediate (IV) by means of MeSO2Cl and TEA in acetonitrile,affording the precursor (VII).Finally,this compound is treated with methanesulfonic acid to afford the target compound.