Sumanirole maleate, U-95666(free base), U-95666E, PNU-95666E, PNU-95666A, U-95666A

1-CBZ-3-哌啶甲醛(R)-5-(甲基氨基)-5,6-二氢-1H-咪唑并[4,5,1-ij]喹啉-2(4h)-酮Chemical Name: 5(R)-(Methylamino)-2,4,5,6-tetrahydro-1H-imidazo[4,5,1-ij]quinolin-2-one maleate
CAS No. 179386-44-8, 194919-11-4 (error), 179386-43-7 (free base)
项目整合开发状态: Discontinued
项目研究机构: Pfizer (Originator)
合成路线:D-Phenylalanine (I) was protected as the methyl carbamate (II) by acylation with methyl chloroformate under Schotten-Baumann conditions.The N-methoxy amide (III) was then prepared by coupling of (II) with O-methyl hydroxylamine in the presence of EDC.Cyclization of (III) to the N-methoxy quinolinone (IV) was accomplished by treatment with bis(trifluoroacetoxy)iodobenzene in the presence of trifluoroacetic acid.Simultaneous reduction of the N-methoxy lactam and carbamate functions of (IV) by means of borane-methyl sulfide complex provided diamine (V).The aliphatic amino group of (V) was then selectively protected as the benzyl carbamate (VI) by using N-(benzyloxycarbonyloxy)succinimide at -40 C.Reaction of (VI) with phosgene,followed by treatment of the intermediate carbamoyl chloride with O-methyl hydroxylamine gave rise to the N-methoxy urea derivative (VII).This was cyclized with bis(trifluoroacetoxy)iodobenzene to the imidazoquinolinone (VIII).The N-methoxy and N-benzyloxycarbonyl groups of (VIII) were then removed by hydrogenolysis in the presence of Pearlman's catalyst,and the title compound was finally converted to the corresponding maleate salt.