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【结 构 式】 
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【分子编号】14066 【品名】methyl 11-methylene-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylate 【CA登记号】 |
【 分 子 式 】C17H14O3 【 分 子 量 】266.29636 【元素组成】C 76.68% H 5.3% O 18.02% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 11-methylene-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylic acid methyl ester (I) with N-methylpiperazine and paraformaldehyde by means of trifluoroacetic acid in hot tetrachloroethane gives 11-[2-(4-methylpiperazin-1-yl)ethylidene]-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylic acid methyl ester (II), which by reaction with ethyl chloroformate and sodium acetate in dichloromethane yields the corresponding 2-chloroethylidene derivative (III). The condensation of (III) with 5,6-dimethyl-1H-benzimidazole (IV) in refluxing toluene affords the methyl ester (V) of the desired product, which is finally hydrolyzed with sodium methoxide in methanol.
| 【1】 Oshima, E.; Obase, H.; Karasawa, A.; Kubo, K.; Miki, I.; Ishii, A. (Kyowa Hakko Kogyo Co., Ltd.); Tricyclic cpds. EP 0345747; JP 1990091040; US 4999363; US 5118701; US 5242931; US 5302596 . |
| 【2】 Prous, J.; Castaner, J.; KW-3635. Drugs Fut 1992, 17, 9, 782. |
| 【3】 Ishii, A.; Higo, K.; Miki, I.; Kubo, K.; Ohshima, E.; Takami, H.; Karasawa, A.; Sato, H.; Obase, H.; Shirakura, S.; Synthesis and biological activity of a novel thromboxane A2 receptor antagonist, KW-3635, and its related derivatives. 11th Symp Med Chem (Dec 4-5, Tokushima) 1990, Abst P-6. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 | |
| (I) | 14066 | methyl 11-methylene-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylate | C17H14O3 | 详情 | 详情 | |
| (II) | 14067 | methyl 11-[(E)-2-(4-methylpiperazino)ethylidene]-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylate | C23H26N2O3 | 详情 | 详情 | |
| (III) | 14068 | methyl 11-[(E)-2-chloroethylidene]-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylate | C18H15ClO3 | 详情 | 详情 | |
| (IV) | 14069 | 5,6-Dimethylbenzimidazole; 5,6-Dimethyl-1H-benzimidazole | 582-60-5 | C9H10N2 | 详情 | 详情 |
| (V) | 14070 | methyl 11-[(E)-2-(5,6-dimethyl-1H-benzimidazol-1-yl)ethylidene]-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylate | C27H24N2O3 | 详情 | 详情 |