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【结 构 式】 
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【药物名称】Soquinolol mucate, We-704, Sertum 【化学名称】5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydro-2(1H)-isoquinolinecarboxaldehyde mucate 【CA登记号】61563-19-7, 63614-17-5 ((2:1) salt), 61563-18-6 (free base), 63614-18-6 (monoacetate salt) 【 分 子 式 】C23H36N2O11 【 分 子 量 】516.55017 |
【开发单位】Abbott (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, beta-Adrenoceptor Antagonists |
合成路线1
The formylation of 5-hydroxy-1,2,3,4-tetrahydroisoquinoline (I) with formamide (II) at 140 C gives N-formyl-5-hydroxy-1,2,3,4-tetrahydroisoquinoline (III), which is condensed with epichlorohydrin (IV) by means of NaOH in water yielding N-formyl-5-(2,3-epoxypropoxy)-1,2,3,4-tetrahydroisoquinoline (V). Finally, this compound is condensed with tert-butylamine (VI).
| 【1】 Knoll, A.-G. (Knoll AG); Isoquinoline derivatives. NL 7513301 . |
| 【2】 Westermann, A.; Zimmermann, F.; Wuppermann, D.; Friedrich, L.; Raschack, M. (Knoll AG.); New isoquinoline derivatives. DE 2620179 . |
| 【3】 Prous, J.; Castaner, J.; SOQUINOLOL MUCATE < Rec INNM >. Drugs Fut 1989, 14, 5, 439. |
| 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) | 20879 | 1,2,3,4-tetrahydro-5-isoquinolinol | C9H11NO | 详情 | 详情 | |
| (III) | 20880 | 5-hydroxy-3,4-dihydro-2(1H)-isoquinolinecarbaldehyde | C10H11NO2 | 详情 | 详情 | |
| (IV) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (V) | 20882 | 5-(2-oxiranylmethoxy)-3,4-dihydro-2(1H)-isoquinolinecarbaldehyde | C13H15NO3 | 详情 | 详情 | |
| (VI) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |