methyl 3-[5-[(2-aminoacetyl)amino]-4-(2-chlorobenzoyl)-2-thienyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】22035

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

【CA登记号】

【分子式】C₁₇H₁₇ClN₂O₄S

【分子量】380.85176

【元素组成】C 53.61% H 4.5% Cl 9.31% N 7.36% O 16.8% S 8.42%

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：(VI)

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.

参考文献中间体

合成目标

【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