4-[3-[2,6-dimethyl-4-thioxo-1(4H)-pyridinyl]propyl]-4-methylmorpholin-4-ium iodide -Drug Synthesis Database

【结构式】

【分子编号】46012

【品名】4-[3-[2,6-dimethyl-4-thioxo-1(4H)-pyridinyl]propyl]-4-methylmorpholin-4-ium iodide

【CA登记号】

【分子式】C₁₅H₂₅IN₂OS

【分子量】408.34685

【元素组成】C 44.12% H 6.17% I 31.08% N 6.86% O 3.92% S 7.85%

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：(VII)

N-(3-Aminopropyl)morpholine (I) was protected as the N-Boc derivative (II) and then quaternized with iodomethane to produce the ammonium salt (III). Subsequent acid deprotection of (III) gave amine (IV). Treatment of 2,6-dimethyl-4-pyrone (V) with Lawesson’s reagent in toluene yielded the thiono derivative (VI), which was coupled with amine (IV) to afford the pyridine thione (VII).

参考文献中间体

合成目标

【1】 Singh, J.; et al.; A practical synthesis of an anti-methicillin resistant Staphylococcus aureus cephalosporin BMS-247243. Org Process Res Dev 2000, 4, 6, 488.
【2】 Kim, O.; et al.; Discovery, synthesis and SAR of BMS-247243, a novel cephalosporin active against methicillin-resistant Staphylococcus aureus (MRSA) and susceptible Staphylococcus aureus (MSSA). 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1062.

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)	25440	3-(4-morpholinyl)-1-propanamine	123-00-2	C₇H₁₆N₂O	详情	详情
(II)	46007	tert-butyl 3-(4-morpholinyl)propylcarbamate		C₁₂H₂₄N₂O₃	详情	详情
(III)	46008	4-[3-[(tert-butoxycarbonyl)amino]propyl]-4-methylmorpholin-4-ium iodide		C₁₃H₂₇IN₂O₃	详情	详情
(IV)	46009	4-(3-aminopropyl)-4-methylmorpholin-4-ium iodide		C₈H₁₉IN₂O	详情	详情
(V)	46010	2,6-dimethyl-4H-pyran-4-one	1004-36-0	C₇H₈O₂	详情	详情
(VI)	46011	2,6-dimethyl-4H-pyran-4-thione		C₇H₈OS	详情	详情
(VII)	46012	4-[3-[2,6-dimethyl-4-thioxo-1(4H)-pyridinyl]propyl]-4-methylmorpholin-4-ium iodide		C₁₅H₂₅IN₂OS	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII)

Acylation of the cephem nucleus (XX) with the intermediate acid (XVI) via activation with either DCC or the Vilsmeier reagent provided amide (XXI). The ester groups of (XXI) were then cleaved with trifluoroacetic acid to give acid (XXII). Finally, condensation of (XXII) with pyridine thione (VII) furnished the title compound.

参考文献中间体

合成目标

【1】 Singh, J.; et al.; A practical synthesis of an anti-methicillin resistant Staphylococcus aureus cephalosporin BMS-247243. Org Process Res Dev 2000, 4, 6, 488.
【3】 Springer, D.M.; Luh, B.Y.; D'Andrea, S.V.; Hudyma, T.W.; Kim, O.K. (Bristol-Myers Squibb Co.); Cephalosporin derivs.. EP 0966472; WO 9823621 .
【2】 Kim, O.; et al.; Discovery, synthesis and SAR of BMS-247243, a novel cephalosporin active against methicillin-resistant Staphylococcus aureus (MRSA) and susceptible Staphylococcus aureus (MSSA). 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1062.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VII)	46012	4-[3-[2,6-dimethyl-4-thioxo-1(4H)-pyridinyl]propyl]-4-methylmorpholin-4-ium iodide	C₁₅H₂₅IN₂OS	详情	详情
(XVI)	46020	2-[[4-((E)-3-[[2-(tert-butoxy)-2-oxoethyl]amino]-3-oxo-1-propenyl)-2,5-dichlorophenyl]sulfanyl]acetic acid	C₁₇H₁₉Cl₂NO₅S	详情	详情
(XX)	31135	benzhydryl (6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₂₁H₁₉ClN₂O₃S	详情	详情
(XXI)	46023	benzhydryl (6R,7R)-7-[(2-[[4-((E)-3-[[2-(tert-butoxy)-2-oxoethyl]amino]-3-oxo-1-propenyl)-2,5-dichlorophenyl]sulfanyl]acetyl)amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₃₈H₃₆Cl₃N₃O₇S₂	详情	详情
(XXII)	46024	(6R,7R)-7-([2-[(4-[(E)-3-[(carboxymethyl)amino]-3-oxo-1-propenyl]-2,5-dichlorophenyl)sulfanyl]acetyl]amino)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	C₂₁H₁₈Cl₃N₃O₇S₂	详情	详情

Extended Information