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【结 构 式】 
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【药物名称】AVP-13358 【化学名称】2-[4-(Adamantan-1-ylcarboxamido)phenyl]-N-(2-pyridyl)-1H-benzimidazole-5-carboxamide 【CA登记号】459805-03-9 【 分 子 式 】C30H29N5O2 【 分 子 量 】491.59793 |
【开发单位】Avanir (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Immunoglobulin E Inhibitors |
合成路线1
The cyclization of 3,4-diaminobenzoic acid (I) with 4-nitrobenzaldehyde (II) in nitrobenzene at 160 C gives 2-(4-nitrophenyl)-1H-benzimidazole-5-carboxylic acid (III), which is condensed with 2-aminopyridine (IV) by means of CDI in DMF to yield the corresponding amide (V). The reduction of the nitro group of (V) with H2 over Pd/C in methanol affords 2-(4-aminophenyl)-N-(2-pyridinyl)-1H-benzimidazole-5-carboxamide (VI). Finally, this compound is condensed with adamantane-1-carboxylic acid (VII) to provide the target diamide.
| 【1】 Sircar, J.C.; Richards, M.L.; Major, M.W. (Avanir Pharmaceuticals); Benzimidazole cpds. for modulating IgE and inhibiting cellular proliferation. EP 1368028; WO 0272090 . |
| 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) | 62528 | C7H8N2O2 | 详情 | 详情 | ||
| (II) | 18184 | 4-Nitrobenzaldehyde | 555-16-8 | C7H5NO3 | 详情 | 详情 |
| (III) | 64591 | 2-(4-nitrophenyl)-1H-benzimidazole-5-carboxylic acid | C14H9N3O4 | 详情 | 详情 | |
| (IV) | 11305 | 2-Pyridinamine; 2-Pyridinylamine; 2-Aminopyridine | 504-29-0 | C5H6N2 | 详情 | 详情 |
| (V) | 64592 | 2-(4-nitrophenyl)-N-(2-pyridinyl)-1H-benzimidazole-5-carboxamide | C19H13N5O3 | 详情 | 详情 | |
| (VI) | 64593 | 2-(4-aminophenyl)-N-(2-pyridinyl)-1H-benzimidazole-5-carboxamide | C19H15N5O | 详情 | 详情 | |
| (VII) | 64594 | tricyclo[3.3.1.1~3,7~]decane-1-carbonyl chloride | C11H15ClO | 详情 | 详情 |