|
【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% |
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 |