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【结 构 式】

【分子编号】58543

【品名】ethyl 4-cyano-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

【CA登记号】

【 分 子 式 】C12H12N4O2

【 分 子 量 】244.25304

【元素组成】C 59.01% H 4.95% N 22.94% O 13.1%

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:(VI)

The condensation between diethyl ethoxymethylenemalonate (I) and 5-amino-1-ethylpyrazole (II) afforded the enamino malonate (III). Cyclization of (III) upon heating at 255 C in diphenyl ether produced the pyrazolopyridine (IV). This was subsequently chlorinated to (V) in refluxing phosphoryl chloride. Alternatively, enamino malonate (III) was directly converted to the chloro pyrazolopyridine (V) by treatment with POCl3. Nitrile (VI) was prepared by displacement of the chloro group of (V) with cyanide in the presence of a phase-transfer catalyst. Cyclization of the cyano ester (VI) with hydrazine led to the pyrazolopyridopyridiazine tricyclic system (VII). Diazotization of amine (VII) generated the dioxo derivative (VIII), which was chlorinated with POCl3 to yield the dichloro derivative (IX). Selective displacement of the 6-chloro group of (IX) with the imidazole carboxamide (X) produced the imidazolyl derivative (XI).

1 Kim, S.; Wang, Y.; Yu, G.; Macor, J.; Chung, H.-J.; Humora, M.; Katipally, K. (Bristol-Myers Squibb Co.); Fused pyridopyridazine inhibitors of cGMP phosphodiesterase. EP 1165521; JP 2002540102; US 6316438; WO 0056719 .
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) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(II) 40098 1-ethyl-1H-pyrazol-5-amine; 1-ethyl-1H-pyrazol-5-ylamine 3528-58-3 C5H9N3 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) 58542 ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate C11H12ClN3O2 详情 详情
(VI) 58543 ethyl 4-cyano-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate C12H12N4O2 详情 详情
(VII) 58544 9-amino-3-ethyl-3,7-dihydro-6H-pyrazolo[4',3':5,6]pyrido[3,4-d]pyridazin-6-one C10H10N6O 详情 详情
(VIII) 58545 3-ethyl-7,8-dihydro-3H-pyrazolo[4',3':5,6]pyrido[3,4-d]pyridazine-6,9-dione C10H9N5O2 详情 详情
(IX) 58546 6,9-dichloro-3-ethyl-3H-pyrazolo[4',3':5,6]pyrido[3,4-d]pyridazine C10H7Cl2N5 详情 详情
(X) 58547 N-methyl-1H-imidazole-4-carboxamide C5H7N3O 详情 详情
(XI) 58548 1-(9-chloro-3-ethyl-3H-pyrazolo[4',3':5,6]pyrido[3,4-d]pyridazin-6-yl)-N-methyl-1H-imidazole-4-carboxamide C15H13ClN8O 详情 详情
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