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【结 构 式】 
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【分子编号】44868 【品名】methyl (Z)-3-(1H-imidazo[4,5-b]pyridin-1-yl)-3-phenyl-2-propenoate 【CA登记号】 |
【 分 子 式 】C16H13N3O2 【 分 子 量 】279.29824 【元素组成】C 68.81% H 4.69% N 15.04% O 11.46% |
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：(XIX)Intermediate (XIV) can be obtained as follows: Bromination of methyl cinnamate (XV) with Br2 in CH2Cl2 provides 2,3-dibromo-3-phenylpropanoate (XVI), which is then converted into alpha-bromocinnamic ester (XVII) by reaction with Et3N in refluxing toluene. Treatment of (XVII) with imidazopyridine (XVIII) and NaH in DMF affords derivative (XIX), which is then hydrolyzed by treatment with NaOH in MeOH to furnish carboxylic acid (XX). Finally, (XX) reacts with carbonylditriazole in DMF to give the target intermediate (XIV).
| 【1】 Hemmerle, H.; Schubert, G.; Burger, H.-J.; Herling, A.; Efendic, S. (Aventis SA); Cyclohexane derivs., processes for their preparation and their use as glucose-6-phosphatase inhibitors. CA 2149007; CA 4416433; EP 0682024; JP 1995330767; US 5739147 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 44863 | C17H12N6O | 详情 | 详情 | ||
| (XV) | 23888 | methyl (E)-3-phenyl-2-propenoate | 103-26-4 | C10H10O2 | 详情 | 详情 |
| (XVI) | 44865 | methyl 2,3-dibromo-3-phenylpropanoate | C10H10Br2O2 | 详情 | 详情 | |
| (XVII) | 44866 | methyl (Z)-2-bromo-3-phenyl-2-propenoate | C10H9BrO2 | 详情 | 详情 | |
| (XVIII) | 44867 | 1H-imidazo[4,5-b]pyridine | C6H5N3 | 详情 | 详情 | |
| (XIX) | 44868 | methyl (Z)-3-(1H-imidazo[4,5-b]pyridin-1-yl)-3-phenyl-2-propenoate | C16H13N3O2 | 详情 | 详情 | |
| (XX) | 44869 | (Z)-3-(1H-imidazo[4,5-b]pyridin-1-yl)-3-phenyl-2-propenoic acid | C15H11N3O2 | 详情 | 详情 | |
| (XXI) | 44870 | di(1H-1,2,4-triazol-1-yl)methanone | C5H4N6O | 详情 | 详情 |
Extended Information