Teniloxazine maleate, Sulfoxazine maleate, Y-8894, Luceran, Metatone
替尼沙秦马来酸盐替尼沙秦Chemical Name: 2-[2-(2-Thenyl)phenoxymethyl]morpholine maleate
CAS No. 62473-80-7, 63342-78-9 (1:1), 62473-79-4 (free base)
项目整合开发状态: Phase III
项目研究机构: Mitsubishi Pharma (Originator)
合成路线:This compound can be obtained in two different ways:1) The acylation of 1-benzylamino-3-[2-(2-thenyl)phenoxy]-2-propanol (I) with chloroacetyl chloride (II) by means of triethylamine in CHCl3 gives N-[2-hydroxy-3-[2-(2-thenyl)phenoxy)propyl]-N-benzylchloroacetamide (III),which is cyclized by treatment with sodium methoxide in refluxing methanol yielding N-benzyl-2-[2-(2-thenyl)phenoxymethyl]morpholin-5-one (IV).The reduction of (IV) with LiAlH4 in refluxing ether affords N-benzyl-2-[2-(2-thenyl)phenoxymethyl]morpholine (V),which is debenzylated by treatment with ethyl chlorotormate (A) in refluxing toluene giving N-ethoxycarbonyl-2-[2-(2-thenyl)phenoxymethyl]morpholine (VI).Finally,this compound is decarboxylated by treatment with barium hydroxide in refluxing water and treated with maleic acid (B).2) By cyclization of 1-[2-(2-thenyl)phenoxy]-2,3-epoxypropane (VII) with 2-aminoethyl hydrogen sulfate (VIII) by means of NaOH in refluxing water.Finally,the resulting compound is treated with maleic acid (B).
📌 参考资料/链接：
参考文献标题:Y-8894
文献作者:Serradell,M.N.; Blancafort,P.; Castar,J.
参考来源:Drugs Fut 1981,6(7),423
📄 详细内容
合成路线:This compound can be obtained in two different ways:1) The acylation of 1-benzylamino-3-[2-(2-thenyl)phenoxy]-2-propanol (I) with chloroacetyl chloride (II) by means of triethylamine in CHCl3 gives N-[2-hydroxy-3-[2-(2-thenyl)phenoxy)propyl]-N-benzylchloroacetamide (III),which is cyclized by treatment with sodium methoxide in refluxing methanol yielding N-benzyl-2-[2-(2-thenyl)phenoxymethyl]morpholin-5-one (IV).The reduction of (IV) with LiAlH4 in refluxing ether affords N-benzyl-2-[2-(2-thenyl)phenoxymethyl]morpholine (V),which is debenzylated by treatment with ethyl chlorotormate (A) in refluxing toluene giving N-ethoxycarbonyl-2-[2-(2-thenyl)phenoxymethyl]morpholine (VI).Finally,this compound is decarboxylated by treatment with barium hydroxide in refluxing water and treated with maleic acid (B).2) By cyclization of 1-[2-(2-thenyl)phenoxy]-2,3-epoxypropane (VII) with 2-aminoethyl hydrogen sulfate (VIII) by means of NaOH in refluxing water.Finally,the resulting compound is treated with maleic acid (B).
参考文献标题:
文献作者:Muro,T.; et al.
参考来源:US 4005084
合成路线:This compound can be obtained in two different ways:1) The acylation of 1-benzylamino-3-[2-(2-thenyl)phenoxy]-2-propanol (I) with chloroacetyl chloride (II) by means of triethylamine in CHCl3 gives N-[2-hydroxy-3-[2-(2-thenyl)phenoxy)propyl]-N-benzylchloroacetamide (III),which is cyclized by treatment with sodium methoxide in refluxing methanol yielding N-benzyl-2-[2-(2-thenyl)phenoxymethyl]morpholin-5-one (IV).The reduction of (IV) with LiAlH4 in refluxing ether affords N-benzyl-2-[2-(2-thenyl)phenoxymethyl]morpholine (V),which is debenzylated by treatment with ethyl chlorotormate (A) in refluxing toluene giving N-ethoxycarbonyl-2-[2-(2-thenyl)phenoxymethyl]morpholine (VI).Finally,this compound is decarboxylated by treatment with barium hydroxide in refluxing water and treated with maleic acid (B).2) By cyclization of 1-[2-(2-thenyl)phenoxy]-2,3-epoxypropane (VII) with 2-aminoethyl hydrogen sulfate (VIII) by means of NaOH in refluxing water.Finally,the resulting compound is treated with maleic acid (B).
参考文献标题:
文献作者:Fukuzawa,S.; et al.
参考来源:JP 76131883
产品链接: CAS No. 62473-80-7›› 产品链接: CAS No.62473-79-4››