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【结 构 式】

【分子编号】59837

【品名】N-(4-nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)-3-isoxazolecarboxamide

【CA登记号】

【 分 子 式 】C12H10N4O5

【 分 子 量 】290.23536

【元素组成】C 49.66% H 3.47% N 19.3% O 27.56%

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:(XIV)

In a related procedure, the pyranopyridine (III) was oxidized to the corresponding N-oxide (X) with 3-chloroperoxybenzoic acid, and the nitro group of (X) was subsequently reduced to amine (XI) by catalytic hydrogenation over Pd/C. Acylation of (XI) with isoxazole-3-carbonyl chloride (IX) provided amide (XII). After pyridine ring nitration with fuming nitric acid to afford (XIII), its N-oxide function was reduced by treatment with phosphorus tribromide. The resultant nitro amide (XIV) was then hydrogenated to the corresponding amino amide derivative (XV), which was finally cyclized in hot ethyleneglycol to the target imidazopyranopyridine

1 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
(III) 59826 3-nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridine C8H8N2O3 详情 详情
(IX) 59832 3-isoxazolecarbonyl chloride C4H2ClNO2 详情 详情
(X) 59833 3-nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-1-ium-1-olate C8H8N2O4 详情 详情
(XI) 59834 3-amino-7,8-dihydro-5H-pyrano[4,3-b]pyridin-1-ium-1-olate C8H10N2O2 详情 详情
(XII) 59835 3-[(3-isoxazolylcarbonyl)amino]-7,8-dihydro-5H-pyrano[4,3-b]pyridin-1-ium-1-olate C12H11N3O4 详情 详情
(XIII) 59836 3-[(3-isoxazolylcarbonyl)amino]-4-nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-1-ium-1-olate C12H10N4O6 详情 详情
(XIV) 59837 N-(4-nitro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)-3-isoxazolecarboxamide C12H10N4O5 详情 详情
(XV) 59838 N-(4-amino-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)-3-isoxazolecarboxamide C12H12N4O3 详情 详情
Extended Information