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【结 构 式】

【分子编号】51038

【品名】ethyl pyrazolo[1,5-a]pyridine-2-carboxylate

【CA登记号】

【 分 子 式 】C10H10N2O2

【 分 子 量 】190.20168

【元素组成】C 63.15% H 5.3% N 14.73% O 16.82%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

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
Extended Information