(E)-2-(5-chloro-2-thienyl)-1-ethenesulfonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】48101

【品名】(E)-2-(5-chloro-2-thienyl)-1-ethenesulfonyl chloride

【CA登记号】

【分子式】C₆H₄Cl₂O₂S₂

【分子量】243.13396

【元素组成】C 29.64% H 1.66% Cl 29.16% O 13.16% S 26.38%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The lithium anion of ethyl methanesulfonate (I) was condensed with ethyl chlorophosphonate to produce the phosphonate (II), which was subsequently subjected to a Wittig reaction with 5-chlorotiophene-2-carboxaldehyde (III), yielding olefin (IV). After cleavage of the ethyl sulfonate of (IV) by means of tetrabutylammonium iodide, treatment with sulfuryl chloride afforded the intermediate sulfonyl chloride (V).

参考文献中间体

合成目标

【2】 Myers, M.R.; Becker, M.R.; Ewing, W.R.; Spada, A.P. (Aventis Pharmaceuticals, Inc.); Substd. oxoazaheterocyclyl factor Xa inhibitors. WO 0032590; WO 0107436 .
【1】 Hanney, B.A.; He, W.; Poli, G.B.; Spada, A.P.; Myers, M.R.; Burns, C.J.; Pauls, H.W.; Jiang, J.Z.; Condon, S.M.; Ewing, W.R.; Becker, M.R.; Li, A.; Choi-Sledeski, Y.M.; Lau, W.F.; Davis, R.S. (Aventis Pharmaceuticals, Inc.); Substd. oxoazaheterocyclyl factor Xa inhibitors. EP 1051176; WO 9937304 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	48097	ethyl methanesulfonate；ethylmesylate;ethyl methanesulphonate；O-ethylmethylsulfonate	62-50-0	C₃H₈O₃S	详情	详情
(II)	48098	ethyl (diethoxyphosphoryl)methanesulfonate		C₇H₁₇O₆PS	详情	详情
(III)	48099	5-chloro-2-thiophenecarbaldehyde	7283-96-7	C₅H₃ClOS	详情	详情
(IV)	48100	ethyl (E)-2-(5-chloro-2-thienyl)-1-ethenesulfonate		C₈H₉ClO₃S₂	详情	详情
(V)	48101	(E)-2-(5-chloro-2-thienyl)-1-ethenesulfonyl chloride		C₆H₄Cl₂O₂S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Coupling of piperazinone (XIV) with sulfonyl chloride (V) gave rise to the sulfonamide (XV). The N-Boc group of (XV) was finally cleaved by treatment with trifluoroacetic acid to afford the title compound.

参考文献中间体

合成目标

【2】 Myers, M.R.; Becker, M.R.; Ewing, W.R.; Spada, A.P. (Aventis Pharmaceuticals, Inc.); Substd. oxoazaheterocyclyl factor Xa inhibitors. WO 0032590; WO 0107436 .
【1】 Hanney, B.A.; He, W.; Poli, G.B.; Spada, A.P.; Myers, M.R.; Burns, C.J.; Pauls, H.W.; Jiang, J.Z.; Condon, S.M.; Ewing, W.R.; Becker, M.R.; Li, A.; Choi-Sledeski, Y.M.; Lau, W.F.; Davis, R.S. (Aventis Pharmaceuticals, Inc.); Substd. oxoazaheterocyclyl factor Xa inhibitors. EP 1051176; WO 9937304 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(V)	48101	(E)-2-(5-chloro-2-thienyl)-1-ethenesulfonyl chloride	C₆H₄Cl₂O₂S₂	详情	详情
(XIV)	48108	tert-butyl 2-[(2-oxo-1-piperazinyl)methyl]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate	C₁₇H₂₂N₄O₃	详情	详情
(XV)	48109	tert-butyl 2-[(4-[[(E)-2-(5-chloro-2-thienyl)ethenyl]sulfonyl]-2-oxo-1-piperazinyl)methyl]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate	C₂₃H₂₅ClN₄O₅S₂	详情	详情

Extended Information