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【结 构 式】

【分子编号】32762

【品名】ethyl 4-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1(6H)-pyridazinyl]butanoate

【CA登记号】

【 分 子 式 】C23H22N4O3

【 分 子 量 】402.45284

【元素组成】C 68.64% H 5.51% N 13.92% O 11.93%

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:(IX)

The Grignard condensation of phenylethynylmagnesium bromide with acetic anhydride in THF gives 4-phenyl-3-butyn-2-one (II), which is cyclized with 1-aminopyridinium iodide (III) by means of KOH in dichloromethane yielding the pyrazolopyridine (IV). The reaction of (IV) with 2-oxoacetic acid (V) by means of acetic acid in dimethoxyethane (DME) affords the butyric acid derivative (VI), which is cyclized with hydrazine in hot DMA to give the pyridazinone (VII). The condensation of (VII) with 4-bromobutyric acid ethyl ester (VIII) by means of benzyltriethylammonium chloride in hot DME/methanol provides the butyric ester intermediate (IX), which is finally hydrolyzed with NaOH.

1 Zanka, A.; et al.; Pilot-scale synthesis of a novel non-xanthine adenosine A1 receptor antagonist. 1,3-dipolar cycloaddition of pyridine N-immine to an acetylene. Org Process Res Dev 1998, 2, 5, 320.
2 Zanka, A.; Efficient large-scale synthesis of 4-phenyl-3-butyn-2-one, a key intermediate for a novel potent adenosine antagonist. Org Process Res Dev 1998, 2, 1, 60.
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) 32758 bromo(2-phenylethynyl)magnesium;phenylacetylenyl magnesium bromide;(phenylethynyl)magnesium bromide C8H5BrMg 详情 详情
(II) 32759 4-phenyl-3-butyn-2-one 1817-57-8 C10H8O 详情 详情
(III) 32760 1-aminopyridinium iodide C5H7IN2 详情 详情
(IV) 32760 1-aminopyridinium iodide C5H7IN2 详情 详情
(V) 15618 2-Oxoacetic acid; Glyoxylic Acid 298-12-4 C2H2O3 详情 详情
(VI) 32761 2-hydroxy-4-oxo-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)butyric acid C17H14N2O4 详情 详情
(VII) 17984 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-3(2H)-pyridazinone C17H12N4O 详情 详情
(VIII) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(IX) 32762 ethyl 4-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1(6H)-pyridazinyl]butanoate C23H22N4O3 详情 详情
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