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【结 构 式】 
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【药物名称】FAUC-213 【化学名称】2-[4-(4-Chlorophenyl)piperazin-1-ylmethyl]pyrazolo[1,5-a]pyridine 【CA登记号】337972-47-1 【 分 子 式 】C18H19ClN4 【 分 子 量 】326.83193 |
【开发单位】Friedrich-Alexander-Universität (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS, Dopamine D4 Antagonists |
合成路线1
The 1,3-dipolar cycloaddition of N-aminopyridinium iodide (I) to dimethyl acetylenedicarboxylate (II) afforded the pyrazolopyridine system (III). Ester groups hydrolysis and regioselective decarboxylation of (III) with hot 50% sulfuric acid gave the mono-carboxylic acid (IV), which was further esterified with ethanol and sulfuric acid. Finally, reductive amination of the ethyl ester (V) with (p-chlorophenyl)piperazine (VI) in the presence of LiAlH4 provided the target compound.
| 【1】 Lober, S.; et al.; Rationally based efficacy tuning of selective dopamine D4 receptor ligands leading to the complete antagonist 2-[4-(4-chlorophenyl) piperazin-1-ylmethyl]pyrazolo[1,5-a]pyridine (FAUC 213). J Med Chem 2001, 44, 17, 2691. |
| 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) | 32760 | 1-aminopyridinium iodide | C5H7IN2 | 详情 | 详情 | |
| (II) | 24551 | Dimethyl acetylenedicarboxylate; Dimethyl 2-butynedioate;Acetylenedicarboxylic acid dimethyl ester | 762-42-5 | C6H6O4 | 详情 | 详情 |
| (III) | 51036 | dimethyl pyrazolo[1,5-a]pyridine-2,3-dicarboxylate | C11H10N2O4 | 详情 | 详情 | |
| (IV) | 51037 | pyrazolo[1,5-a]pyridine-2-carboxylic acid | C8H6N2O2 | 详情 | 详情 | |
| (V) | 51038 | ethyl pyrazolo[1,5-a]pyridine-2-carboxylate | C10H10N2O2 | 详情 | 详情 | |
| (VI) | 33593 | 1-(4-chlorophenyl)piperazine | 38869-46-4 | C10H13ClN2 | 详情 | 详情 |