Succinchlorimide; N-Chlorosuccinimide; 1-chloro-2,5-pyrrolidinedione -Drug Synthesis Database

【结构式】

【分子编号】40429

【品名】Succinchlorimide; N-Chlorosuccinimide; 1-chloro-2,5-pyrrolidinedione

【CA登记号】128-09-6

【分子式】C₄H₄ClNO₂

【分子量】133.534

【元素组成】C 35.98% H 3.02% Cl 26.55% N 10.49% O 23.96%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(II)

By oxidation of cyclosporin D (I) with N-chlorosuccinimide (II) and dimethylsulfide in toluene.

参考文献中间体

合成目标

【1】 Robinson, C.; Castaner, J.; PSC-833. Drugs Fut 1995, 20, 10, 1010.
【2】 Bollinger, P.; Bolsterli, J.J.; Borel, J.-F.; Krieger, M.; Payne, T.G.; Traber, R.P.; Wenger, R. (Novartis AG); Cyclosporins and their use as pharmaceuticals. AU 8817679; EP 0296122; JP 1989045396; JP 1996048696; US 5525590 .

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)	15475	(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexenyl]-6,9,18,24-tetraisobutyl-3,21,30-triisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone		C₆₃H₁₁₃N₁₁O₁₂	详情	详情
(II)	40429	Succinchlorimide; N-Chlorosuccinimide; 1-chloro-2,5-pyrrolidinedione	128-09-6	C₄H₄ClNO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(A)

It is prepared in two different ways, both starting from 6-methyl-8-methanesulfonyloxymethylergolin (II), m.p. 192-4 C, prepared by reaction of the corresponding hydroxy compound (I) with methanesulfonyl chloride in pyridine: 1) The starting product (II) is first chlorinated with N-chlorosuccinimide (A) in dioxane to 2-chloro-6-methyl-8-methanesulfonyloxymethylergolin (III), which is then treated with sodium cyanide in DMSO. 2) The starting product (II) is first treated with sodium cyanide in DMSO to give 6-methyl-8-cyanomethylergolin (IV), which is then chlorinated with N-chlorosuccinimide (A) in dioxane.

参考文献中间体

合成目标

【1】 Castañer, J.; Chatterjee, S.S.; Lergotrile. Drugs Fut 1976, 1, 2, 63.
【2】 Clemens, J.A.; et al. (Eli Lilly and Company); D-6-methyl-2,8-disubstituted ergolines. DE 2335750; ES 446789; FR 2193606; GB 1423065; JP 57081487 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	40429	Succinchlorimide; N-Chlorosuccinimide; 1-chloro-2,5-pyrrolidinedione	128-09-6	C₄H₄ClNO₂	详情	详情
(I)	10051	[(6aR,9R,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]methanol; 9,10-Dyhydrosergol	18051-16-6	C₁₆H₂₀N₂O	详情	详情
(II)	40428	(6aR,9R,10aR)-7-methyl-9-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline		C₁₉H₂₆N₂OS	详情	详情
(III)	40430	(6aR,9R,10aR)-5-chloro-7-methyl-9-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline		C₁₉H₂₅ClN₂OS	详情	详情
(IV)	40431	2-[(6aR,9S,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]acetonitrile		C₁₇H₁₉N₃	详情	详情

合成路线3

该中间体在本合成路线中的序号：(XVIII)

The reaction of the already reported amide (VIII) with phosphonate salt (XV) gives the succinimide ammonium salt (XVI), which is finally treated with HCl in acetone to yield the target quaternary ammonium chloride derivative. The phosphonate salt (XV) is obtained by reaction of trimethyl phosphite (XVII) with N-chlorosuccinimide (XVIII) in trimethyl phosphate.

参考文献中间体

合成目标

【1】 Ikemoto, T.; et al.; Convenient efficient synthesis of TAK-779, a nonpeptide CCR5 antagonist: Development of preparation of various ammonium salts using trialkylphosphite and N-halogenosuccinimide. Tetrahedron 2001, 57, 8, 1525.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	55371			C₂H₆ClO₃P	详情	详情
(VIII)	31567	2-(4-methylphenyl)-N-(4-[[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl)-6,7-dihydro-5H-benzo[a]cycloheptene-8-carboxamide		C₃₂H₃₆N₂O₂	详情	详情
(XV)	55369			C₇H₁₃ClNO₅P	详情	详情
(XVI)	55370			C₃₇H₄₃N₃O₄	详情	详情
(XVII)	12642	Trimethyl phosphite	121-45-9	C₃H₉O₃P	详情	详情
(XVIII)	40429	Succinchlorimide; N-Chlorosuccinimide; 1-chloro-2,5-pyrrolidinedione	128-09-6	C₄H₄ClNO₂	详情	详情

Extended Information