药物详细合成路线
| Name | WB-4101 | | Chemical Name | 2-[2-(2,6-Dimethoxyphenoxy)ethylaminomethyl]-1,4-benzodioxane | | CAS | 613-67-2 | | Related CAS | | | Formula | C19H23NO5 | | Structure |  | | Formula Weight | 345.39886 | | Stage | 未确定 | | Company | | | Activity/Mechanism | alpha1-Adrenoceptor Antagonists | | Syn. Route | 1 | | Route 1 | | by condensation of 2-aminomethyl-1,4-benzodioxane (i) with 2,6-dimethoxyphenoxyethyl chloride (ii) performed by heating at 160 c or by means of k2co3 in refluxing chcl3 - water.the starting products (i) and (ii) are prepared as follows:1) the reaction of 2-chloromethyl-1,4-benzodioxane (iii) with potassium phthalimide (iv) in refluxing dmf gives 2-phthalimidomethyl-1,4-benzodioxane (v), which is then treated with hydrazine hydrate (a) in refluxing 2-ethoxyethanol to give (i).2) the condensation of 2,6-dimethoxyphenol (vi) with ethylene carbonate (vii) by means of k2co3 in refluxing toluene gives 2,6-dimethoxyphenoxyethanol (viii), which is then refluxed with socl2 to afford (ii). | | |  | | List of intermediates | No. | | 1,4-dihydroestronemethylether; (8r,9s,13s,14s)-3-methoxy-13-methyl-1,4,6,7,8,9,11,12,13,14,15,16-dodecahydro-17h-cyclopenta[a]phenanthren-17-one | (vi) | | (3r)-3-(stearoyloxy)tetradecanoic acid | (a) | | octahydropyrrolo[1,2-a]pyrazine | (iv) | | [4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridinyl]methanol | (vii) | | n(1)-(6-chloro-1-naphthyl)-1,2-ethanediamine; n-(2-aminoethyl)-n-(6-chloro-1-naphthyl)amine | (iii) | | | (v) | | 1,6-dichloronaphthalene | (i) | | 4-amino-n-[(1s)-2-amino-1-(4-chlorobenzyl)-2-oxoethyl]-8-chromanecarboxamide | (viii) | | (2s)-2-(2-fluoro[1,1-biphenyl]-4-yl)propionic acid | (ii) | | | Reference 1: us 3472874 . Reference 2: castaner, j.; serradell, m.n.; hillier, k.; blancafort, p.; wb-4101. drugs fut 1979, 4, 5, 369. Reference 3: green, p.n.; et al.; synthesis and pharmacological properties of a series of 2-(substituted-aminoethyl)-1,4-benzodioxanes. j med chem 1969, 12, 2, 326-329. |
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