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【结 构 式】

【分子编号】59830

【品名】3-amino-4-nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-1-ium-1-olate

【CA登记号】

【 分 子 式 】C8H9N3O4

【 分 子 量 】211.17728

【元素组成】C 45.5% H 4.3% N 19.9% O 30.31%

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:(VII)

3-Nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridine (III) was prepared by heating tetrahydropyranone (I) with dinitropyridone (II) in methanolic ammonia following a reported procedure. Hydrogenation of the nitro derivative (III) and protection of the resulting amine (IV) with trichloroacetyl chloride afforded the trichloroacetamide (V). Oxidation of the pyridine ring of (V) with 3-chloroperoxybenzoic acid gave the N-oxide (VI). Nitration of the pyridine ring of (VI) with fuming nitric acid, followed by amide hydrolysis with ammonium hydroxide provided the 3-amino-4-nitropyridine N-oxide (VII). Reduction of the N-oxide and 4-nitro groups of (VII) was accomplished in a single step by hydrogenation in the presence of Raney-nickel to furnish the bicyclic diaminopyridine (VIII). Subsequent monoacylation of (VIII) with isoxazole-3-carbonyl chloride (IX) followed by thermal cyclization provided the desired imidazopyranopyridine compound (1,2), which was finally isolated as the title phosphate salt

1 Takada, S.; Sasatani, T.; Chomei, N.; Adachi, M.; Fujishita, T.; Eigyo, M.; Murata, S.; Kawasaki, K.; Matsushita, A.; Synthesis and structure-activity relationships of fused imidazopyridines: A new series of benzodiazepine receptor ligands. J Med Chem 1996, 39, 14, 2844.
2 Takada, S.; Sasatani, T.; Chomei, N.; Adachi, M.; Matsushita, A. (Shionogi & Co. Ltd.); Condensed imidazopyridine derivs. with psychotropic activity. EP 0556008; JP 1993286973; US 5378848; US 5461062 .
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) 31563 tetrahydro-4H-pyran-4-one 29943-42-8 C5H8O2 详情 详情
(II) 59825 1-methyl-3,5-dinitro-2(1H)-pyridinone C6H5N3O5 详情 详情
(III) 59826 3-nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridine C8H8N2O3 详情 详情
(IV) 59827 7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-amine; 7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-ylamine C8H10N2O 详情 详情
(V) 59828 2,2,2-trichloro-N-(7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)acetamide C10H9Cl3N2O2 详情 详情
(VI) 59829 3-[(2,2,2-trichloroacetyl)amino]-7,8-dihydro-5H-pyrano[4,3-b]pyridin-1-ium-1-olate C10H9Cl3N2O3 详情 详情
(VII) 59830 3-amino-4-nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-1-ium-1-olate C8H9N3O4 详情 详情
(VIII) 59831 3-amino-7,8-dihydro-5H-pyrano[4,3-b]pyridin-4-ylamine; 7,8-dihydro-5H-pyrano[4,3-b]pyridine-3,4-diamine C8H11N3O 详情 详情
(IX) 59832 3-isoxazolecarbonyl chloride C4H2ClNO2 详情 详情
Extended Information