• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】14070

【品名】methyl 11-[(E)-2-(5,6-dimethyl-1H-benzimidazol-1-yl)ethylidene]-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylate

【CA登记号】

【 分 子 式 】C27H24N2O3

【 分 子 量 】424.49924

【元素组成】C 76.4% H 5.7% N 6.6% O 11.31%

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:(V)

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
Extended Information