methyl (5R)-5-methyl-4-oxotetrahydro-3-thiophenecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】22082

【品名】methyl (5R)-5-methyl-4-oxotetrahydro-3-thiophenecarboxylate

【CA登记号】

【分子式】C₇H₁₀O₃S

【分子量】174.2206

【元素组成】C 48.26% H 5.79% O 27.55% S 18.41%

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：(II)

The condensation of 1 2-benzenediamine (I) with methyltetrahydro-5-methyl 4-oxo-3-thiophenecarboxylate (II) in toluene using a Dean-Stark trap gives the triyclic system (III), which is dehydrogenated to 4,9-dihydro-3-methyl-10H-thienol[3,4-b][1,5]benzodiazepin-10-one (IV). Treatment of (IV) with chloroacetyl chloride in dioxane in the presence of K2CO3 yields 4-chloroacetyl-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one (V), which is finally reacted with N-methylpiperazine to produce telenzepine, which is isolated as the hydrochloride.

参考文献中间体

合成目标

【1】 Borner, H.; Haffer, G.; Sauer, G. (Schering AG); Process for the preparation of 2-bromo-8-ergolinyl. DE 3340025; US 4970314 .
【2】 Galvan, M.; Eltze, M.; Figala, V.; TELENZEPINE HYDROCHLORIDE < Rec INN >. Drugs Fut 1988, 13, 4, 327.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	10061	1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine	109-01-3	C₅H₁₂N₂	详情	详情
(A)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(I)	12824	2-Aminophenylamine; o-Phenylenediamine; 1,2-Benzenediamine	95-54-5	C₆H₈N₂	详情	详情
(II)	11372	Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate		C₅H₉NO₂	详情	详情
(II)	22082	methyl (5R)-5-methyl-4-oxotetrahydro-3-thiophenecarboxylate		C₇H₁₀O₃S	详情	详情
(III)	22083	(3R)-3-methyl-1,3,4,9-tetrahydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one		C₁₂H₁₂N₂OS	详情	详情
(III)	22088	2-[4-(3,4-dichlorophenyl)-1-piperazinyl]ethyl 3-oxobutanoate		C₁₆H₂₀Cl₂N₂O₃	详情	详情
(IV)	22084	3-methyl-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one		C₁₂H₁₀N₂OS	详情	详情
(V)	22085	4-(2-chloroacetyl)-3-methyl-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one		C₁₄H₁₁ClN₂O₂S	详情	详情

Extended Information