ethyl 2-[2,3-dihydro-1,4-benzodioxin-5-yl(2-ethoxy-2-oxoethyl)amino]acetate -Drug Synthesis Database

【结构式】

【分子编号】64784

【品名】ethyl 2-[2,3-dihydro-1,4-benzodioxin-5-yl(2-ethoxy-2-oxoethyl)amino]acetate

【CA登记号】

【分子式】C₁₆H₂₁NO₆

【分子量】323.34588

【元素组成】C 59.43% H 6.55% N 4.33% O 29.69%

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：(IV)

The reaction of 4-aminobenzoic acid ethyl ester (I) with acryloyl chloride (II) by means of TEA in dichloromethane gives the corresponding acrylamide (III), which is condensed with 4,5,6,7-tetrahydro-1H-indol-4-one (IV) by means of K2CO3 in hot DMF to yield NEO-339. (1,2)

参考文献中间体

合成目标

【1】 Mohan, P.; Fick, D.B.; McKinley, L.K.; Prigaro, B.J.; Pfadenhauer, E.; Helton, D.; Search, design and discovery of NEO-339, a novel agent that increases attentional processes associated with cognition. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 249.
【2】 Foreman, M.M.; Glasky, A.J.; Fick, D.B. (Spectrum Pharmaceuticals, Inc.); Synthesis and methods of use of tetrahydroisoindolone analogues and derivs.. EP 1383742; WO 0285856 .

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)	16498	Benzocaine; ethyl 4-aminobenzoate	94-09-7	C₉H₁₁NO₂	详情	详情
(II)	11577	Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride	814-68-6	C₃H₃ClO	详情	详情
(III)	64783	ethyl 4-(acryloylamino)benzoate		C₁₂H₁₃NO₃	详情	详情
(IV)	64784	ethyl 2-[2,3-dihydro-1,4-benzodioxin-5-yl(2-ethoxy-2-oxoethyl)amino]acetate		C₁₆H₂₁NO₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The intermediate dimesylate (VI) can be obtained as follows: The condensation of 2,3-dihydro-1,4-benzodioxin-5-amine (I) with ethyl bromoacetate (II) by means of Hunig's base and NaI in refluxing toluene gives the tertiary amine (III), which is reduced by means of LiAlH4 in THF to yield the diethanolamine (IV). Finally, this compound is esterified by means of mesyl chloride (V) to provide the desired dimesylate intermediate (VI). Alternatively, the diethanolamine (IV) can be obtained by direct condensation of 2,3-dihydro-1,4-benzodioxin-5-amine (I) with 2-chloroethanol (VII) by means of Hunig's base.

参考文献中间体

合成目标

【1】 Jirkovsky, I.; Zeldis, J.; Chan, A.W.-Y.; Fiegelson, G.B. (Wyeth); Preparation of N1-(2'-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines. WO 0378396 .

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)	22000	2,3-dihydro-1,4-benzodioxin-5-amine; 2,3-dihydro-1,4-benzodioxin-5-ylamine; 5-Amino-1,4-benzodioxane	16081-46-2	C₈H₉NO₂	详情	详情
(II)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(III)	64784	ethyl 2-[2,3-dihydro-1,4-benzodioxin-5-yl(2-ethoxy-2-oxoethyl)amino]acetate		C₁₆H₂₁NO₆	详情	详情
(IV)	64785	2-[2,3-dihydro-1,4-benzodioxin-5-yl(2-hydroxyethyl)amino]-1-ethanol		C₁₂H₁₇NO₄	详情	详情
(V)	13467	Methanesulfonyl chloride;Mesyl chloride;Methylsulfonyl chloride;Methanesulfonic acid chloride;Methanesulfonyl chloride;Methanesulphonyl chloride	124-63-0	CH₃ClO₂S	详情	详情
(VI)	64786	2-(2,3-dihydro-1,4-benzodioxin-5-yl{2-[(methylsulfonyl)oxy]ethyl}amino)ethyl methanesulfonate		C₁₄H₂₁NO₈S₂	详情	详情
(VII)	10384	2-Chloro-1-ethanol; Ethylene chlorohydrin	107-07-3	C₂H₅ClO	详情	详情

Extended Information