(3S,4R)-4-[[(1R,6S)-4-(2-chlorobenzyl)-5-oxo-3,4-diazabicyclo[4.1.0]hept-2-en-2-yl]oxy]-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbonitrile -Drug Synthesis Database

【结构式】

【分子编号】44165

【品名】(3S,4R)-4-[[(1R,6S)-4-(2-chlorobenzyl)-5-oxo-3,4-diazabicyclo[4.1.0]hept-2-en-2-yl]oxy]-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbonitrile

【CA登记号】

【分子式】C₂₄H₂₂ClN₃O₄

【分子量】451.9092

【元素组成】C 63.79% H 4.91% Cl 7.85% N 9.3% O 14.16%

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)

Condensation of 1,2-cyclo-propanedicarboxylic anhydride (I) with chlorobenzylhydrazine derivative (II) in EtOH (1) or acetonitrile affords derivative (III), which then reacts with epoxy-benzopyrancarbonitrile derivative (IV) in the presence of pyridine in EtOH to yield a mixture of two diastereomers (Va-b), from which the desired product is chromatographically separated.

参考文献中间体

合成目标

【1】 Mimura, T.; Kubo, H. (Daiichi Pharmaceutical Co., Ltd.); Diazabicycloalkene derivs.. EP 0571822; JP 1994025233; US 5418232 .
【2】 Horino, H.; Mimura, T.; Kobayashi, S.; Ohta, M.; Kubo, H.; Ito, K.; Tsumura, M.; Kitagawa, M.; Novel potassium channel opener prodrugs with a slow onset and prolonged duration of action. Chem Pharm Bull 2000, 48, 4, 490.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	44161	3-oxabicyclo[3.1.0]hexane-2,4-dione	C₅H₄O₃	详情	详情
(II)	44162	1-(2-chlorobenzyl)hydrazine	C₇H₉ClN₂	详情	详情
(III)	44163	3-(2-chlorobenzyl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione	C₁₂H₁₁ClN₂O₂	详情	详情
(IV)	14639	(1aS,7bS)-2,2-dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile	C₁₂H₁₁NO₂	详情	详情
(V)	44164	(3S,4R)-4-[[(1S,6R)-4-(2-chlorobenzyl)-5-oxo-3,4-diazabicyclo[4.1.0]hept-2-en-2-yl]oxy]-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbonitrile	C₂₄H₂₂ClN₃O₄	详情	详情
(VI)	44165	(3S,4R)-4-[[(1R,6S)-4-(2-chlorobenzyl)-5-oxo-3,4-diazabicyclo[4.1.0]hept-2-en-2-yl]oxy]-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbonitrile	C₂₄H₂₂ClN₃O₄	详情	详情

Extended Information