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【结 构 式】 
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【药物名称】Etazolate, SQ-20009(hydrochloride) 【化学名称】1-Ethyl-4-(isopropylidenehydrazino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 【CA登记号】51022-77-6, 35838-58-5 (HCl) 【 分 子 式 】C14H19N5O2 【 分 子 量 】289.33983 |
【开发单位】Bristol-Myers Squibb (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
The condensation of 1-ethyl-5-aminopyrazole (I) with diethyl ethoxymethylenemalonate (II) by heating at 120 C gives diethyl [((1-ethyl-5-pyrazolyl)amino)methylene]malonate (III), which by heating at 235-5 C in diphenyl ether is converted into ethyl 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (IV). The reaction of (IV) with ethyl iodide (A) and K2CO3 in DMF affords ethyl 1-ethyl-4-ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (V), which is condensed with hydrazine in refluxing ethanol with ZnCl2 yielding ethyl 1-ethyl-4-hydrazino-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (VI). Finally, (VI) is condensed with refluxing acetone (B).
| 【1】 Hoehn, H.; Chasin, M. (Bristol-Myers Squibb Co.); Hydrazines and hydrazones of pyrazolopyridine carboxylic acids and esters. DE 2028869; GB 1317797; NL 165461C; NL 7008768 . |
| 【2】 Chatterjee, S.S.; Etazolate. Drugs Fut 1977, 2, 4, 243. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10925 | Iodoethane;ethyl iod | 75-03-6 | C2H5I | 详情 | 详情 |
| (B) | 23199 | 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether | 67-64-1 | C3H6O | 详情 | 详情 |
| (I) | 40098 | 1-ethyl-1H-pyrazol-5-amine; 1-ethyl-1H-pyrazol-5-ylamine | 3528-58-3 | C5H9N3 | 详情 | 详情 |
| (II) | 14088 | Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate | 87-13-8 | C10H16O5 | 详情 | 详情 |
| (III) | 40099 | diethyl 2-[[(1-ethyl-1H-pyrazol-5-yl)amino]methylene]malonate | C13H19N3O4 | 详情 | 详情 | |
| (IV) | 40100 | ethyl 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate | C11H13N3O3 | 详情 | 详情 | |
| (V) | 40101 | ethyl 4-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate | C13H17N3O3 | 详情 | 详情 | |
| (VI) | 40102 | ethyl 1-ethyl-4-hydrazino-1H-pyrazolo[3,4-b]pyridine-5-carboxylate | C11H15N5O2 | 详情 | 详情 |