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【结 构 式】 
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【分子编号】59844 【品名】4-chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-amine; 4-chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-ylamine 【CA登记号】 |
【 分 子 式 】C8H9ClN2O 【 分 子 量 】184.62504 【元素组成】C 52.04% H 4.91% Cl 19.2% N 15.17% O 8.67% |
合成路线1
该中间体在本合成路线中的序号：(XXI)In a different synthetic strategy, dienamine (XVIII) was obtained by heating the tetrahydropyranone enamine (XVI) with the (aminomethylene)oxazolone (XVII) in the presence of Ac2O in toluene. Thermal cyclization of (XVIII) in hot N-methylpyrrolidinone gave rise to the pyridopyranone (XIX). Upon chlorination of pyridone (XIX) with POCl3 in the presence of DMF, a simultaneous displacement of the benzoyl group occurred, leading to the formamidino derivative (XX), which was further hydrolyzed to the 3-amino-4-chloropyridine (XXI) under acidic conditions. Acylation of amine (XXI) with acid chloride (IX) afforded the corresponding amide (XXII). This was converted to the required amidine (XXIII) by chlorination with PCl5, followed by treatment with isopropanolic ammonia. Finally, the tricyclic imidazo-fused compound was obtained by thermal cyclization of the chloro amidine (XXIII) in NMP at 215 C
| 【1】 Adachi, M.; Chomei, N.; Takada, S.; Intramolecular transfer of an alkenyl group in enamines: Application to synthesis of [b]-fused pyridines. Tetrahedron Lett 1996, 37, 49, 8871. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 59832 | 3-isoxazolecarbonyl chloride | C4H2ClNO2 | 详情 | 详情 | |
| (XVI) | 59839 | 4-(3,6-dihydro-2H-pyran-4-yl)morpholine | C9H15NO2 | 详情 | 详情 | |
| (XVII) | 59840 | 4-[(E)-aminomethylidene]-2-phenyl-1,3-oxazol-5(4H)-one | C10H8N2O2 | 详情 | 详情 | |
| (XVIII) | 59841 | 4-[(E)-(3,6-dihydro-2H-pyran-4-ylamino)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one | C15H14N2O3 | 详情 | 详情 | |
| (XIX) | 59842 | N-(4-oxo-1,5,7,8-tetrahydro-4H-pyrano[4,3-b]pyridin-3-yl)benzamide | C15H14N2O3 | 详情 | 详情 | |
| (XX) | 59843 | N'-(4-chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)-N,N-dimethyliminoformamide | C11H14ClN3O | 详情 | 详情 | |
| (XXI) | 59844 | 4-chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-amine; 4-chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-ylamine | C8H9ClN2O | 详情 | 详情 | |
| (XXII) | 59846 | N-(4-chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)-3-isoxazolecarboxamide | C12H10ClN3O3 | 详情 | 详情 | |
| (XXIII) | 59845 | N'-(4-chloro-7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)-3-isoxazolecarboximidamide | C12H11ClN4O2 | 详情 | 详情 |