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【结 构 式】 
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【分子编号】58433 【品名】S-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) dimethylcarbamothioate 【CA登记号】 |
【 分 子 式 】C12H12N2O3S 【 分 子 量 】264.30496 【元素组成】C 54.53% H 4.58% N 10.6% O 18.16% S 12.13% |
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：(III)Condensation of 4-methyl-7-hydroxypyrano[2,3-b]pyridin-2-one (I) with N,N-dimethylthiocarbamoyl chloride gives the thiocarbamate (II), which undergoes thermal rearrangement at 220 C to the S-aryl thiocarbamate isomer (III). Subsequent alkaline hydrolysis of (III) provides the 7-mercapto azacoumarin (IV). Alkylation of (IV) with chloroacetone (V) affords thioether (VI). This compound is finally cyclized to the target pyranothienopyridine compound under alkaline conditions.
| 【1】 Via, L.D.; et al.; Synthesis, photobiological activity and photoreactivity of methyl-thieno-8-azacoumarins, novel bioisosters of psoralen. Bioorg Med Chem Lett 2002, 12, 9, 1253. |
| 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) | 58431 | 7-hydroxy-4-methyl-2H-pyrano[2,3-b]pyridin-2-one | C9H7NO3 | 详情 | 详情 | |
| (II) | 58432 | O-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) dimethylcarbamothioate | C12H12N2O3S | 详情 | 详情 | |
| (III) | 58433 | S-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) dimethylcarbamothioate | C12H12N2O3S | 详情 | 详情 | |
| (IV) | 58434 | 4-methyl-7-sulfanyl-2H-pyrano[2,3-b]pyridin-2-one | C9H7NO2S | 详情 | 详情 | |
| (V) | 15288 | 1-Chloroacetone; Chloroacetone | 78-95-5 | C3H5ClO | 详情 | 详情 |
| (VI) | 58435 | 4-methyl-7-[(2-oxopropyl)sulfanyl]-2H-pyrano[2,3-b]pyridin-2-one | C12H11NO3S | 详情 | 详情 |
Extended Information