Semaxanib, Semoxind, TSU-16, NSC-696819, SU-5416

1,3-二氢-3-[(3,5-二甲基-1H-吡咯-2-基)亚甲基]-2H-吲哚-2-酮Chemical Name: (Z)-3-(3,5-Dimethylpyrrol-2-ylmethylene)indolin-2-one
CAS No. 204005-46-9
项目整合开发状态: Phase II
项目研究机构: Sugen (Originator), Esteve (Licensee), Taiho (Licensee), M.D. Anderson Cancer Center (Codevelopment)
合成路线:Vilsmeier reaction between 2,4-dimethylpyrrole (I) and dimethylformamide (II) by means of phosphorous oxychloride in dichloroethane provides carbaldehyde (III),which is then condensed with 2-indolinone (IV) in ethanol in the presence of piperidine.

合成路线:Title compound was prepared by condensation of oxindole (I) and formylpyrrole (II) in the presence of a catalytic amount of piperidine in refluxing EtOH.

合成路线:The reaction of 1-phenylpiperazine (I) with DMF and POCl3 in dichloroethane gives 4-(4-formylpiperazin-1-yl)benzaldehyde (II),which is condensed with indolin-2-one (III) by means of piperidine in refluxing ethanol.

合成路线:Aldehyde (II) was prepared by Vilsmeier-Haack formylation of 2,4-dimethylpyrrole (I).Subsequent condensation of the pyrrole aldehyde (II) with 5-chlorooxindole (III) in the presence of piperidine furnished the title compound.