2-([2-[(2-hydroxyethyl)amino]ethyl]amino)-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】38377

【品名】2-([2-[(2-hydroxyethyl)amino]ethyl]amino)-1-ethanol

【CA登记号】4439-20-7

【分子式】C₆H₁₆N₂O₂

【分子量】148.20532

【元素组成】C 48.63% H 10.88% N 18.9% O 21.59%

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：(II)

The condensation of 2-bromo-N,N-bis(benzyloxycarbonylmethyl)acetamide (I) with N,N'-bis(2-hydroxyethyl)ethylene-1,2-diamine (II) by means of TEA in DMF gives the corresponding bis-adduct (III). The monoacylation of (III) with butyryl chloride (IV) and DMAP in THF yields the monobutyrate (V), which is acylated with acetyl chloride (VI) and DMAP in THF affording the mixed diester monoacetate monobutyrate (VII). The deprotection of (VII) by hydrogenation with H2 over Pd/C in ethanol provides the tetraacetic acid (VIII), which is finally treated with gadolinium trichloride and NaOH to furnish the target compound.

参考文献中间体

合成目标

【1】 Saab-Ismail, N.H.; et al.; Synthesis and in vivo evaluation of new contrast agents for cardiac MRI. J Med Chem 1999, 42, 15, 2852.

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)	38376	benzyl 2-[[2-(benzyloxy)-2-oxoethyl](2-bromoacetyl)amino]acetate		C₂₀H₂₀BrNO₅	详情	详情
(II)	38377	2-([2-[(2-hydroxyethyl)amino]ethyl]amino)-1-ethanol	4439-20-7	C₆H₁₆N₂O₂	详情	详情
(III)	38378	dibenzyl 3,12-bis[2-(benzyloxy)-2-oxoethyl]-6,9-bis(2-hydroxyethyl)-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioate		C₄₆H₅₄N₄O₁₂	详情	详情
(IV)	10792	Butanoyl chloride; Butyryl chloride	141-75-3	C₄H₇ClO	详情	详情
(V)	38379	dibenzyl 3,12-bis[2-(benzyloxy)-2-oxoethyl]-6-[2-(butyryloxy)ethyl]-9-(2-hydroxyethyl)-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioate		C₅₀H₆₀N₄O₁₃	详情	详情
(VI)	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情
(VII)	38380	dibenzyl 6-[2-(acetoxy)ethyl]-3,12-bis[2-(benzyloxy)-2-oxoethyl]-9-[2-(butyryloxy)ethyl]-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioate		C₅₂H₆₂N₄O₁₄	详情	详情
(VIII)	38381	6-[2-(acetoxy)ethyl]-9-[2-(butyryloxy)ethyl]-3,12-bis(carboxymethyl)-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioic acid		C₂₄H₃₈N₄O₁₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Treatment of N,N'-bis(2-hydroxyethyl)ethylenediamine (I) with p-toluenesulfonyl chloride in pyridine afforded the tretratosyl derivative (II). The disodium salt (IV) prepared from tritosyl diethylenetriamine (III) was then condensed with (II) in hot DMF to produce the macrocyclic compound (V). Cleavage of the N-tosyl groups of (V) to afford (VI) was effected by treatment with H2SO4 at 110 C. Quaternization of triethylamine with 1,3-dibromopropane (VII) gave rise to ammonium salt (VIII). Macrocycle (VI) was then alkylated with bromide (VIII) to furnish (IX). Then, complexation of (IX) with 99TcO2 was carried out by treatment with radiolabeled sodium pertechnetate in the presence of SnCl2.

参考文献中间体

合成目标

【1】 Nicolas, C.; et al.; Synthesis of N-quaternary ammonium [3H] and [99mTc]polyazamacrocycles, potential radiotracers for cartilage imaging. J Label Compd Radiopharm 2000, 43, 6, 585.

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)	38377	2-([2-[(2-hydroxyethyl)amino]ethyl]amino)-1-ethanol	4439-20-7	C₆H₁₆N₂O₂	详情	详情
(II)	46447	2-([(4-methylphenyl)sulfonyl][2-[[(4-methylphenyl)sulfonyl](2-[[(4-methylphenyl)sulfonyl]oxy]ethyl)amino]ethyl]amino)ethyl 4-methylbenzenesulfonate		C₃₄H₄₀N₂O₁₀S₄	详情	详情
(III)	46448	4-methyl-N-[2-[[(4-methylphenyl)sulfonyl](2-[[(4-methylphenyl)sulfonyl]amino]ethyl)amino]ethyl]benzenesulfonamide		C₂₅H₃₁N₃O₆S₃	详情	详情
(IV)	46449			C₂₅H₂₉N₃Na₂O₆S₃	详情	详情
(V)	46450	1,4,7,10,13-pentakis[(4-methylphenyl)sulfonyl]-1,4,7,10,13-pentaazacyclopentadecane		C₄₅H₅₅N₅O₁₀S₅	详情	详情
(VI)	46451	1,4,7,10,13-pentaazacyclopentadecane		C₁₀H₂₅N₅	详情	详情
(VII)	12581	1,3-Dibromopropane	109-64-8	C₃H₆Br₂	详情	详情
(VIII)	46452	3-bromo-N,N,N-triethyl-1-propanaminium bromide		C₉H₂₁Br₂N	详情	详情
(IX)	46453	N,N,N-triethyl-3-(1,4,7,10,13-pentaazacyclopentadecan-1-yl)-1-propanaminium bromide		C₁₉H₄₅BrN₆	详情	详情

Extended Information