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【结 构 式】 
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【分子编号】22040 【品名】3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid 【CA登记号】 |
【 分 子 式 】C18H15ClN4O2S 【 分 子 量 】386.86156 【元素组成】C 55.89% H 3.91% Cl 9.16% N 14.48% O 8.27% S 8.29% |
合成路线1
该中间体在本合成路线中的序号：(XI)Starting from 4-dicarbethoxybutan-1-one (I) and o-chlorocyanoacetophenone (II), in the presence of sufur the aminobenzoylthiophene (III) was obtained. Saponification, decarboxylation and esterification yielded the mono ester (IV), which was acetylated to (V). Amination and ring closure gave the corresponding diazepinone (VII). Sulfuration of (VII), treatment with hydrazine and then with orthoacetate yielded the triazolo compound (X). Saponification of (X) and amidation with morpholine in the presence of carbodiimidazole gave WEB 2086.
| 【1】 Weber, K.-H.; Bechtel, W.D.; Brotizolam radioimmunoassay: Development, evaluati. J Pharm Sci 1985, 74, 1265. |
| 【2】 Weber, K.-H.; Walther, G.; Harreus, A.; Casals Stenzel, J.; Muacevic, G.; Tröger, W. (Boehringer Ingelheim GmbH); Thieno-triazolo-1,4-diazepino-2-carboxamides, proc. AU 8652728; DE 3502392; EP 0194416; ES 8802426; ES 8802523; JP 1986176591; JP 1990191281; US 4968794; US 5082839; US 5155103 . |
| 【3】 Weber, K.H.; WEB 2086. Drugs Fut 1988, 13, 3, 242. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 | |
| (I) | 12923 | 3-(2-Chlorophenyl)-3-oxopropanenitrile | 40018-25-5 | C9H6ClNO | 详情 | 详情 |
| (II) | 22030 | diethyl 2-(3-oxopropyl)malonate | C10H16O5 | 详情 | 详情 | |
| (III) | 22032 | diethyl 2-[[5-amino-4-(2-chlorobenzoyl)-2-thienyl]methyl]malonate | C19H20ClNO5S | 详情 | 详情 | |
| (IV) | 22033 | methyl 3-[5-amino-4-(2-chlorobenzoyl)-2-thienyl]propanoate | C15H14ClNO3S | 详情 | 详情 | |
| (V) | 22034 | methyl 3-[5-[(2-bromoacetyl)amino]-4-(2-chlorobenzoyl)-2-thienyl]propanoate | C17H15BrClNO4S | 详情 | 详情 | |
| (VI) | 22035 | methyl 3-[5-[(2-aminoacetyl)amino]-4-(2-chlorobenzoyl)-2-thienyl]propanoate | C17H17ClN2O4S | 详情 | 详情 | |
| (VII) | 22036 | methyl 3-[5-(2-chlorophenyl)-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-7-yl]propanoate | C17H15ClN2O3S | 详情 | 详情 | |
| (VIII) | 22037 | methyl 3-[5-(2-chlorophenyl)-2-thioxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-7-yl]propanoate | C17H15ClN2O2S2 | 详情 | 详情 | |
| (IX) | 22038 | methyl 3-[5-(2-chlorophenyl)-2-[(Z)hydrazono]-1,3-dihydro-2H-thieno[2,3-e][1,4]diazepin-7-yl]propanoate | C17H17ClN4O2S | 详情 | 详情 | |
| (X) | 22039 | methyl 3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propanoate | C19H17ClN4O2S | 详情 | 详情 | |
| (XI) | 22040 | 3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid | C18H15ClN4O2S | 详情 | 详情 |