PD-161989

Chemical Name: 6-Methyl-7-nitro-5-(pyrrolidin-1-ylmethyl)quinoxaline-2,3(1H,4H)-dione
CAS No. 186268-07-5
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:2-Amino-6-methylbenzoic acid (I) was reduced to alcohol (II) using LiAlH4,and then acetylated in Ac2O at 50 C.The acetyl protected compound (III) was nitrated with HNO3 in AcOH to afford (IV),which was hydrolyzed to the nitroaniline (V) with methanolic KOH.Subsequent condensation with pyrrolidine (VI) in the presence of diethyl azodicarboxylate and triphenylphosphine provided tertiary amine (VII).Hydrogenation of the nitro group of (VII) over Raney-Ni gave phenylenediamine (VIII),which was cyclized with dimethyl oxalate to produce quinoxalinedione (IX).This was finally nitrated with KNO3 in H2SO4 to furnish the title compound.