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【结 构 式】

【分子编号】22033

【品名】methyl 3-[5-amino-4-(2-chlorobenzoyl)-2-thienyl]propanoate

【CA登记号】

【 分 子 式 】C15H14ClNO3S

【 分 子 量 】323.7998

【元素组成】C 55.64% H 4.36% Cl 10.95% N 4.33% O 14.82% S 9.9%

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)

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
Extended Information