JTE-907

Chemical Name: N-(1,3-Benzodioxol-5-ylmethyl)-7-methoxy-2-oxo-8-(pentyloxy)-1,2-dihydroquinoline-3-carboxamide
项目整合开发状态: Discontinued
项目研究机构: Japan Tobacco (Originator)
合成路线:3-Hydroxy-4-methoxy-2-nitrobenzaldehyde (II) was prepared by nitration of isovanillin (I) with fuming nitric acid in cold HOAc.Subsequent alkylation of the phenolic hydroxyl of (II) with n-pentyl bromide yielded the corresponding pentyl ether (III).The nitro group of (III) was then reduced to amine (IV) employing tin chloride in EtOH.Condensation of amino aldehyde (IV) with dimethyl malonate under Knoevenagel conditions furnished the quinolinone derivative (V).Saponification of the ester group of (V),followed by activation of the resultant carboxylic acid (VI) with SOCl2,gave rise to the acid chloride (VII).This was then coupled with 3,4-(methylenedioxy)benzylamine (VIII) to provide the target amide.