1-methoxy-2,3-dihydro-1H-inden-2-yl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】60988

【品名】1-methoxy-2,3-dihydro-1H-inden-2-yl methanesulfonate

【CA登记号】

【分子式】C₁₁H₁₄O₄S

【分子量】242.29576

【元素组成】C 54.53% H 5.82% O 26.41% S 13.23%

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)

This compound can be prepared by three different related ways: 1) By condensation of 1-methoxy-2-aminoindane (I) with 3-bromopropyl diethylamine (II) by means of sodium amide in refluxing toluene (1). 2) The reaction of (I) with 1-chloro-3-bromopropane (III) by heating at 100 C gives the corresponding N-(3-chloropropyl) derivative (IV), which is then condensed with diethylamine by means of NaI in refluxing ethanol (2). 3) By condensation of 1-methoxy-2-indanyl methanesulfonate (V) with N-(diethylaminopropyl)aniline (VI) in refluxing ethanol (2).

参考文献中间体

合成目标

【1】 (A. Christiaens SA); .
【2】 Vanhoof, P.; De Ridder, R. (A. Christiaens SA); CA 1068239; CH 617663; DD 123598; ZA 7607468 .
【3】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Thorpe, P.J..; Moxaprindine. Drugs Fut 1981, 6, 6, 354.

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)	60986	1-methoxy-N-phenyl-2-indanamine; N-(1-methoxy-2,3-dihydro-1H-inden-2-yl)-N-phenylamine		C₁₆H₁₇NO	详情	详情
(II)	60989	3-bromo-N,N-diethyl-1-propanamine; N-(3-bromopropyl)-N,N-diethylamine		C₇H₁₆BrN	详情	详情
(III)	10358	1-Bromo-3-chloropropane	109-70-6	C₃H₆BrCl	详情	详情
(IV)	60987	N-(3-chloropropyl)-1-methoxy-N-phenyl-2-indanamine; N-(3-chloropropyl)-N-(1-methoxy-2,3-dihydro-1H-inden-2-yl)-N-phenylamine		C₁₉H₂₂ClNO	详情	详情
(V)	60988	1-methoxy-2,3-dihydro-1H-inden-2-yl methanesulfonate		C₁₁H₁₄O₄S	详情	详情
(VI)	60990	N-(3-anilinopropyl)-N,N-diethylamine; N~1~,N~1~-diethyl-N~3~-phenyl-1,3-propanediamine		C₁₃H₂₂N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Alkylation of ethyl 4-nitropyrrole-2-carboxylate (I) with 3-methylbutyl bromide (II) in the presence of NaOMe affords the N-isoamyl pyrrole (III). Saponification of the ethyl ester group of (III), followed by treatment of the resultant carboxylic acid (IV) with SOCl2 provides acid chloride (V). This is subsequently coupled with 3-aminopropionitrile (VI) to yield the N-(2-cyanoethyl) amide (VII). Conversion of the cyano group of (VII) into the N-methyl amidine (VIII) is then accomplished under Pinner reaction conditions. Reduction of the nitro group of (VIII) by catalytic hydrogenation over Pd/C furnishes the intermediate aminopyrrole (IX).

参考文献中间体

合成目标

【1】 Roberts, C.D.; Keicher, J.D.; Dyatkina, N.B.; et al.; Minor groove DNA binders as antimicrobial agents. 1. Pyrrole tetraamides are potent antibacterials against vancomycin resistant Enteroccoci and methicillin resistant Staphylococcus aureus. J Med Chem 2002, 45, 4, 805.
【2】 Dyatkina, N.; Hanson, E.; Liehr, S.; et al.; Synthesis, SAR and antimicrobial activity of pyrrole tetraamides. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 62.
【3】 Nelson, P.H.; Muchowski, J.M.; Dyatkina, N.B.; Shi, D.-F.; Zhang, W.; Liehr, S.J.R.; Velligan, M.D.; Botyanszki, J.; Roberts, C.D.; Khorlin, A. (Genelabs Technologies, Inc.); Novel cpds. possessing antibacterial, antifungal or antitumor activity. WO 0200650 .

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)	60988	1-methoxy-2,3-dihydro-1H-inden-2-yl methanesulfonate		C₁₁H₁₄O₄S	详情	详情
(II)	46234	1-bromo-3-methylbutane		C₅H₁₁Br	详情	详情
(III)	54019	ethyl 1-isopentyl-4-nitro-1H-pyrrole-2-carboxylate		C₁₂H₁₈N₂O₄	详情	详情
(IV)	54020	1-isopentyl-4-nitro-1H-pyrrole-2-carboxylic acid		C₁₀H₁₄N₂O₄	详情	详情
(V)	54021	1-isopentyl-4-nitro-1H-pyrrole-2-carbonyl chloride		C₁₀H₁₃ClN₂O₃	详情	详情
(VI)	38094	3-aminopropanenitrile	151-18-8	C₃H₆N₂	详情	详情
(VII)	54022	N-(2-cyanoethyl)-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide		C₁₃H₁₈N₄O₃	详情	详情
(VIII)	60999	N-[3-imino-3-(methylamino)propyl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide		C₁₄H₂₃N₅O₃	详情	详情
(IX)	61000	4-amino-N-[3-imino-3-(methylamino)propyl]-1-isopentyl-1H-pyrrole-2-carboxamide		C₁₄H₂₅N₅O	详情	详情

Extended Information