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【结 构 式】 
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【药物名称】386/1634, FCE-386/1634 【化学名称】1,4-Diethyl-5-(N-isopropylthiocarbamoyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine 【CA登记号】70651-76-2 【 分 子 式 】C14H24N4S 【 分 子 量 】280.43818 |
【开发单位】Pfizer (Originator) 【药理作用】Antiulcer Drugs, GASTROINTESTINAL DRUGS |
合成路线1
The tetahydroimidazopyridine (I) is prepared by condensation of histamine with propionaldehyde in the presence of NaOH. The alkylation in position 1 or 3 is performed with ethyl bromide in a catalytic two-phase system, after protection of the amine group in position 5 as benzyloxycarbonyl derivative, and followed by removal of the protecting group by catalytic hydrogenation. The resulting amines (IVa-b) are then made to react with isopropyl isothiocyanate and the two regioisomers obtained are separated by crystallization.
| 【1】 Acari, G.; Bernardi, L.; Falconi, G.; Scarponi, U. (Pharmacia Corp.); 4,5,6,7-Tetrahydroimidazo[4,5-c]pyridine derivatives. BE 0871985; DE 2849572; FR 2433022; GB 2028798; JP 55024158; US 4223146 . |
| 【2】 Riva, F.; 386/1634. Drugs Fut 1985, 10, 2, 101. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IVa) | 28915 | benzyl 1,4-diethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate | C18H23N3O2 | 详情 | 详情 | |
| (IVb) | 28916 | benzyl 3,4-diethyl-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate | C18H23N3O2 | 详情 | 详情 | |
| (Va) | 28917 | 1,4-diethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine | C10H17N3 | 详情 | 详情 | |
| (Vb) | 28918 | 3,4-diethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine | C10H17N3 | 详情 | 详情 | |
| (VIIa) | 28920 | 1,4-diethyl-N-isopropyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carbothioamide | C14H24N4S | 详情 | 详情 | |
| (VIIb) | 28921 | 3,4-diethyl-N-isopropyl-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carbothioamide | C14H24N4S | 详情 | 详情 | |
| (I) | 28913 | 4-ethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine | C8H13N3 | 详情 | 详情 | |
| (II) | 10101 | Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene | 501-53-1 | C8H7ClO2 | 详情 | 详情 |
| (III) | 28914 | benzyl 4-ethyl-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate | C16H19N3O2 | 详情 | 详情 | |
| (VI) | 28919 | 2-isothiocyanatopropane | 2253-73-8 | C4H7NS | 详情 | 详情 |