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【结 构 式】

【分子编号】40101

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

【CA登记号】

【 分 子 式 】C13H17N3O3

【 分 子 量 】263.2964

【元素组成】C 59.3% H 6.51% N 15.96% O 18.23%

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 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
Extended Information