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【结 构 式】

【分子编号】57734

【品名】2-Indanyl p-toluenesulphonate

【CA登记号】17783-69-6

【 分 子 式 】C16H16O3S

【 分 子 量 】288.36724

【元素组成】C 66.64% H 5.59% O 16.64% S 11.12%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

Alkylation of isovanillin (I) with 2-indanyl tosylate (II) produces the corresponding indanyl ether (III). Subsequent reduction of the aldehyde function of (III) with NaBH4 yields the benzylic alcohol (IV), which is converted to chloride (V) by treatment with SOCl2. Displacement of chloride (V) by KCN in hot DMF gives nitrile (VI). The phenylacetonitrile (VI) is then converted to the homologous phenylpropionitrile derivative (VII) by alkylation with iodomethane in the presence of LDA. Further cyano group reduction in (VII) by hydrogenation over Raney Ni provides amine (VIII). Condensation of amine (VIII) with diphenyl N-cyanocarbonimidate affords the N-cyano isourea (IX) which, after reaction with 2,2-dimethoxyethylamine (X), yields the cyano guanidine (XI). Finally, cyclization of (XI) under acidic conditions gives rise to the target 2-(cyanoimino)imidazole derivative.

1 Diaz, A.; Andres, J.I.; Alonso, J.M.; et al.; Synthesis and biological evaluation of imidazol-2-one and 2-cyanoiminoimidazole derivatives: Novel series of PDE4 inhibitors. Bioorg Med Chem Lett 2002, 12, 4, 653.
2 Freyne, E.J.E.; Fernandez-Gadea, F.J.; Andres-Gil, J.I. (Janssen Pharmaceutica NV); PDE IV inhibiting 2-cyanoiminoimidazole derivs.. WO 9814432 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18455 3-hydroxy-4-methoxybenzaldehyde; Isovanillin 621-59-0 C8H8O3 详情 详情
(II) 57734 2-Indanyl p-toluenesulphonate 17783-69-6 C16H16O3S 详情 详情
(III) 57735 3-(2,3-dihydro-1H-inden-2-yloxy)-4-methoxybenzaldehyde C17H16O3 详情 详情
(IV) 57736 [3-(2,3-dihydro-1H-inden-2-yloxy)-4-methoxyphenyl]methanol C17H18O3 详情 详情
(V) 57737 2-[5-(chloromethyl)-2-methoxyphenoxy]indane; 4-(chloromethyl)-2-(2,3-dihydro-1H-inden-2-yloxy)phenyl methyl ether C17H17ClO2 详情 详情
(VI) 57738 2-[3-(2,3-dihydro-1H-inden-2-yloxy)-4-methoxyphenyl]acetonitrile C18H17NO2 详情 详情
(VII) 57739 2-[3-(2,3-dihydro-1H-inden-2-yloxy)-4-methoxyphenyl]propanenitrile C19H19NO2 详情 详情
(VIII) 57740 2-[3-(2,3-dihydro-1H-inden-2-yloxy)-4-methoxyphenyl]-1-propanamine; 2-[3-(2,3-dihydro-1H-inden-2-yloxy)-4-methoxyphenyl]propylamine C19H23NO2 详情 详情
(IX) 57741 2-[5-(2-{[(cyanoimino)(phenoxy)methyl]amino}-1-methylethyl)-2-methoxyphenoxy]indane C27H27N3O3 详情 详情
(X) 34158 aminoacetaldehyde dimethylacetal; 2,2-dimethoxy-1-ethanamine; 2,2-dimethoxyethylamine 22483-09-6 C4H11NO2 详情 详情
(XI) 57742 N''-cyano-N-{2-[3-(2,3-dihydro-1H-inden-2-yloxy)-4-methoxyphenyl]propyl}-N'-(2,2-dimethoxyethyl)guanidine C25H32N4O4 详情 详情
Extended Information