N,N-bis(2-methoxyethyl)amine; 2-methoxy-N-(2-methoxyethyl)-1-ethanamine -Drug Synthesis Database

【结构式】

【分子编号】23785

【品名】N,N-bis(2-methoxyethyl)amine; 2-methoxy-N-(2-methoxyethyl)-1-ethanamine

【CA登记号】111-95-5

【分子式】C₆H₁₅NO₂

【分子量】133.19064

【元素组成】C 54.11% H 11.35% N 10.52% O 24.02%

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)

Condensation of 5-amino-4,6-dichloro-2-methylpyrimidine (I) and 2-bromo-4-isopropylaniline (II) in boiling ethoxyethanol gave diarylamine (III). Subsequent diazotization of (III) using NaNO2 and AcOH produced the triazolopyrimidine (IV), which was finally condensed with bis(2-methoxyethyl)amine (V) in the presence of Et3N in refluxing EtOH to provide the title compound.

参考文献中间体

合成目标

【1】 Wilde, R.G.; Curry, M.; Cheeseman, R.S.; Bakthavatchalam, R.; Gilligan, P.J.; Hobbs, F.W.; Rescinito, J.P.; Chorvat, R.J.; Cocuzza, A.J.; Beck, J.P.; Synthesis, corticotropin-releasing factor receptor. J Med Chem 1999, 42, 5, 833.

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)	23537	4,6-dichloro-2-methyl-5-pyrimidinamine; 4,6-dichloro-2-methyl-5-pyrimidinylamine		C₅H₅Cl₂N₃	详情	详情
(II)	23782	2-bromo-4-isopropylaniline; 2-bromo-4-isopropylphenylamine	51605-97-1	C₉H₁₂BrN	详情	详情
(III)	23783	N(4)-(2-bromo-4-isopropylphenyl)-6-chloro-2-methyl-4,5-pyrimidinediamine; N-(5-amino-6-chloro-2-methyl-4-pyrimidinyl)-N-(2-bromo-4-isopropylphenyl)amine		C₁₄H₁₆BrClN₄	详情	详情
(IV)	23784	3-(2-bromo-4-isopropylphenyl)-7-chloro-5-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine		C₁₄H₁₃BrClN₅	详情	详情
(V)	23785	N,N-bis(2-methoxyethyl)amine; 2-methoxy-N-(2-methoxyethyl)-1-ethanamine	111-95-5	C₆H₁₅NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Treatment of 2,6-dimethoxy-4-methylphenol (I) with 2-bromobutyryl bromide (II) and Et3N in dichloromethane provides 2,6-dimethoxy-4-methylphenyl ester (III), which is converted into the target product by reaction with bis(2-methoxyethyl)amine (IV) and Et3N in refluxing toluene. The target (R)-enantiomer is isolated by resolution of the racemic amino ester by either enantiospecific enzyme hydrolysis of the corresponding (S)-isomer or by means of chiral HPLC.

参考文献中间体

合成目标

【1】 Bennett, D.J.; Belelli, D.; Anderson, A.; et al.; alpha-Amino acid phenolic ester derivatives: Novel water-soluble general anesthetic agents which allosterically modulate GABAA receptors. J Med Chem 2001, 44, 22, 3582.
【2】 Hamilton, N.M. (Akzo Nobel N.V.); alpha-Amino acid phenyl ester derivs.. EP 1098871; WO 0005196 .

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)	47212	2,6-dimethoxy-4-methylphenol		C₉H₁₂O₃	详情	详情
(II)	47213	2-bromobutanoyl bromide	26074-52-2	C₄H₆Br₂O	详情	详情
(III)	47214	2,6-dimethoxy-4-methylphenyl 2-bromobutanoate		C₁₃H₁₇BrO₄	详情	详情
(IV)	23785	N,N-bis(2-methoxyethyl)amine; 2-methoxy-N-(2-methoxyethyl)-1-ethanamine	111-95-5	C₆H₁₅NO₂	详情	详情
(V)	56452	2,6-dimethoxy-4-methylphenyl 2-[bis(2-methoxyethyl)amino]butanoate		C₁₉H₃₁NO₆	详情	详情

Extended Information