新产品编号:737721

Chemical Name: 6-Chloro-2-(2-hydroxybiphenyl-3-yl)-1H-indole-5-carboxamidine
CAS No. 277312-21-7
项目整合开发状态: Preclinical
项目研究机构: Celera (Originator)
合成路线:The ammonolysis of the cyano group of 4-amino-2-chlorobenzonitrile (I) with Me3Al and NH4Cl in refluxing p-xylene gives the benzamidine (II),which by reaction with NaNO2 and HCl,followed by reduction with SnCl2,yields 4-carboxamidino-3-clorophenylhydrazine (III).The condensation of (III) with acetophenone (IV) by means of TEA in refluxing ethanol affords the corresponding hydrazone (V),which is finally submitted to a Fisher indolization reaction with PPA at 155?C,providing a mixture of the 4-chloro and the target 6-chloro regioisomers that is resolved by preparative HPLC.

合成路线:The reaction of 4-amino-2-chloro-5-iodobenzonitrile (VI) with Ms-Cl gives the corresponding mesylate (VII),which is cyclized with 3-ethynyl-2-methoxybiphenyl (VIII) by means of Pd(PPh3)2Cl2,CuI,TEA and TBAF or NaOH to yield the O-protected cyanoindole (IX).Finally,this compound is treated with hydroxylamine in refluxing ethanol and deprotected with HOAc,Ac2O and Zn to afford the target indole carboxamidine compound.