1-methyl-1H-imidazol-2-ylhydrosulfide; 1-methyl-1H-imidazole-2-thiol -Drug Synthesis Database

【结构式】

【分子编号】18783

【品名】1-methyl-1H-imidazol-2-ylhydrosulfide; 1-methyl-1H-imidazole-2-thiol

【CA登记号】60-56-0

【分子式】C₄H₆N₂S

【分子量】114.17112

【元素组成】C 42.08% H 5.3% N 24.54% S 28.09%

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：(I)

C-10213-Go has been synthesized from 1-methyl-2-mercaptoimidazole (I). When (I) is methylated with methyl iodide it gives the corresponding thiomethyl derivative (II). Nitration of (II) yields the nitro derivative (III). Oxidation of (III) with monoperphthalic acid gives the sulfone (IV). Condensation of (IV) with 1-methanesulfonyl-2-imidazolidinone (VI) in the presence of sodium hydride affords C-10213-Go.

参考文献中间体

合成目标

【1】 Arya, V.P.; Satranidazole. Drugs Fut 1983, 8, 9, 797.

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)	13467	Methanesulfonyl chloride;Mesyl chloride;Methylsulfonyl chloride;Methanesulfonic acid chloride;Methanesulfonyl chloride;Methanesulphonyl chloride	124-63-0	CH₃ClO₂S	详情	详情
(A)	34077	2-carboperoxybenzoic acid		C₈H₆O₅	详情	详情
(I)	18783	1-methyl-1H-imidazol-2-ylhydrosulfide; 1-methyl-1H-imidazole-2-thiol	60-56-0	C₄H₆N₂S	详情	详情
(II)	36225	1-methyl-2-(methylsulfanyl)-1H-imidazole; methyl 1-methyl-1H-imidazol-2-yl sulfide		C₅H₈N₂S	详情	详情
(III)	36226	methyl 1-methyl-5-nitro-1H-imidazol-2-yl sulfide; 1-methyl-2-(methylsulfanyl)-5-nitro-1H-imidazole		C₅H₇N₃O₂S	详情	详情
(IV)	36227	1-methyl-2-(methylsulfonyl)-5-nitro-1H-imidazole; methyl 1-methyl-5-nitro-1H-imidazol-2-yl sulfone		C₅H₇N₃O₄S	详情	详情
(V)	36228	2-imidazolidinone	120-93-4	C₃H₆N₂O	详情	详情
(VI)	36229	1-(methylsulfonyl)-2-imidazolidinone	41730-79-4	C₄H₈N₂O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXVII)

Reaction of mesylate (XVII) with triazole sodium salt (XVIII) gave (XIX). Ozonization of olefinic double bond, followed by treatment with Me2S and K2CO3 provided ketone (XX). Then, haloform reaction with NaOBr gave acid (XXI), and reduction with LiAlH4 in cold Et2O afforded primary alcohol (XXII). Alcohol (XXII) was converted to mesylate (XXIII), and this was condensed with 4-(trifluoromethoxy)phenol (XXIV) to give ether (XXV). Deprotection of the trityl group with formic acid in EtOAc and subsequent reaction with methanesulfonyl chloride provided mesylate (XXVI), which was finally condensed with mercaptoimidazole (XXVII) to furnish the target compound.

参考文献中间体

合成目标

【1】 Tsukuda, T.; Watanabe, M.; Ontsuka, H.; Hattori, K.; Shirai, M.; Shimma, N.; Synthesis of novel antifungal agents (2). Bioorg Med Chem Lett 1998, 8, 14, 1825.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVII)	18762	1-Ethoxyethylene; Ethyl vinyl ether；Ethoxyethene	109-92-2	C₄H₈O	详情	详情
(XVIII)	16341	1H-1,2,4-triazol-1-ylsodium		C₂H₂N₃Na	详情	详情
(XIX)	18775	2-[(1S,2R,3R,4R)-4-isopropenyl-2-methoxy-1-methyl-3-(1H-1,2,4-triazol-1-ylmethyl)cyclohexyl]ethyl trityl ether; 1-([(1R,2R,3S,6R)-6-isopropenyl-2-methoxy-3-methyl-3-[2-(trityloxy)ethyl]cyclohexyl]methyl)-1H-1,2,4-triazole		C₃₅H₄₁N₃O₂	详情	详情
(XX)	18776	1-[(1R,2R,3R,4S)-3-methoxy-4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-4-[2-(trityloxy)ethyl]cyclohexyl]-1-ethanone		C₃₄H₃₉N₃O₃	详情	详情
(XXI)	18777	(1R,2R,3R,4S)-3-methoxy-4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-4-[2-(trityloxy)ethyl]cyclohexanecarboxylic acid		C₃₃H₃₇N₃O₄	详情	详情
(XXII)	18778	[(1R,2R,3R,4S)-3-methoxy-4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-4-[2-(trityloxy)ethyl]cyclohexyl]methanol		C₃₃H₃₉N₃O₃	详情	详情
(XXIII)	18779	[(1R,2R,3R,4S)-3-methoxy-4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-4-[2-(trityloxy)ethyl]cyclohexyl]methyl methanesulfonate		C₃₄H₄₁N₃O₅S	详情	详情
(XXIV)	18780	4-(trifluoromethoxy)phenol	828-27-3	C₇H₅F₃O₂	详情	详情
(XXV)	18781	1-([(1R,2R,3S,6R)-2-methoxy-3-methyl-6-[[4-(trifluoromethoxy)phenoxy]methyl]-3-[2-(trityloxy)ethyl]cyclohexyl]methyl)-1H-1,2,4-triazole; 2-((1S,2R,3R,4R)-2-methoxy-1-methyl-3-(1H-1,2,4-triazol-1-ylmethyl)-4-[[4-(trifluoromethoxy)phenoxy]methyl]cyclohexyl)ethyl trityl ether		C₄₀H₄₂F₃N₃O₄	详情	详情
(XXVI)	18782	2-((1S,2R,3R,4R)-2-methoxy-1-methyl-3-(1H-1,2,4-triazol-1-ylmethyl)-4-[[4-(trifluoromethoxy)phenoxy]methyl]cyclohexyl)ethyl methanesulfonate		C₂₂H₃₀F₃N₃O₆S	详情	详情
(XXVII)	18783	1-methyl-1H-imidazol-2-ylhydrosulfide; 1-methyl-1H-imidazole-2-thiol	60-56-0	C₄H₆N₂S	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

Condensation of 3-chloro-4-fluoronitrobenzene (I) with the sodium derivative of 2-mercapto-1-methylimidazole (II) affords the diaryl sulfide (III). Subsequent nitro group reduction in (III) using iron dust and ammonium chloride provides the intermediate aniline (IV).

参考文献中间体

合成目标

【1】 Dutia, M.; Powell, D.W.; Berger, D.M.; et al.; Synthesis and evaluation of 4-anilino substituted 3-quinolinecarbonitriles as inhibitors of kinases of the Ras-MAPK signaling cascade. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 105.

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)	58441	2-chloro-1-fluoro-4-nitrobenzene; 3-Chloro-4-fluoronitrobenzene; 4-Fluoro-3-chloronitrobenzene	350-30-1	C₆H₃ClFNO₂	详情	详情
(II)	18783	1-methyl-1H-imidazol-2-ylhydrosulfide; 1-methyl-1H-imidazole-2-thiol	60-56-0	C₄H₆N₂S	详情	详情
(III)	58442	2-chloro-4-nitrophenyl 1-methyl-1H-imidazol-2-yl sulfide; 2-[(2-chloro-4-nitrophenyl)sulfanyl]-1-methyl-1H-imidazole		C₁₀H₈ClN₃O₂S	详情	详情
(IV)	58443	3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]aniline; 3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]phenylamine		C₁₀H₁₀ClN₃S	详情	详情

Extended Information