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【结 构 式】 
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【分子编号】36653 【品名】2-imidazo[1,2-a]pyridin-3-ylacetic acid 【CA登记号】 |
【 分 子 式 】C9H8N2O2 【 分 子 量 】176.1748 【元素组成】C 61.36% H 4.58% N 15.9% O 18.16% |
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：(IV)The cyclization of 2-aminopyridine (I) with ethyl 4-bromoacetoacetate (II) by means of NaHCO3 in hot dioxane gives the imidazopyridine (III), which is hydrolyzed at the ester function with KOH in ethanol yielding the free acid (IV) . Finally, the treatment of acid (IV) with phosphorous acid and PCl3 in chlorobenzene at 115 C, followed by hydrolysis in boiling 6N HCl yielded the target bisphosphonate.
| 【1】 Atsumi, T.; et al.; JP 7688965 . |
| 【2】 Takeuchi, M.; Sakamoto, S.; Kawamuki, K.; Kurihara, H.; Nakahara, H.; Isomura, Y.; Studies on novel bone resorption inhibitors. II. Synthesis and pharmacological activities of fused aza-heteroarylbisphosphonate derivatives. Chem Pharm Bull 1998, 46, 11, 1703. |
| 【3】 Isomura, Y.; Takeuchi, M.; Abe, T. (Yamanouchi Pharmaceutical Co., Ltd.); Heterocyclic biphosphonic acid derivs.. EP 0354806; US 4990503; US 5039669 . |
| 【4】 Casagrande, C.; et al.; Synthesis and pharmacological activity of imidazo-[1,2-a]pyridine-2-acetic and -2,3-dicarboxylic acid and related compounds. Farmaco 1968, 23, 12, 1141. |
| 【5】 Ishii, M.; Takaoka, K. (Yamanouchi Pharmaceutical Co., Ltd.); Novel preparation method of heterocyclic bis(phosphonic acid) derivs.. JP 1999269184 . |
| 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) | 11305 | 2-Pyridinamine; 2-Pyridinylamine; 2-Aminopyridine | 504-29-0 | C5H6N2 | 详情 | 详情 |
| (II) | 36651 | Ethyl (bromoacetyl)acetate;ethyl 4-bromo-3-oxobutanoate | 13176-46-0 | C6H9BrO3 | 详情 | 详情 |
| (III) | 36652 | ethyl 2-imidazo[1,2-a]pyridin-3-ylacetate | C11H12N2O2 | 详情 | 详情 | |
| (IV) | 36653 | 2-imidazo[1,2-a]pyridin-3-ylacetic acid | C9H8N2O2 | 详情 | 详情 |
Extended Information