2-azidophenethylamine; 2-(2-azidophenyl)-1-ethanamine -Drug Synthesis Database

【结构式】

【分子编号】42246

【品名】2-azidophenethylamine; 2-(2-azidophenyl)-1-ethanamine

【CA登记号】

【分子式】C₈H₁₀N₄

【分子量】162.19436

【元素组成】C 59.24% H 6.21% N 34.54%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

Acetonitrile derivative (I) is treated with BuLi and alkylated with 3-bromopropanol (A) to yield alcohol (II), which is further alkylated by means of LICKOR (n-BuLi/t-BuOK) and 1-chloro-3-bromopropane (B) to afford (III). Reaction of derivative (III) with secondary amine (VIII) in acetonitrile gives (IV). Amine (VIII) is obtained by trifluoroacetylation of azide (VI) with trifluoroacetic anhydride to yield (VII), which is then N-methylated by means of MeI and hydrolyzed with KOH. Finally, alcohol (IV) reacts with succinimido biotinate (V) in DMSO to provide the desired product.

参考文献中间体

合成目标

【1】 Teodori, E.; et al.; Synthesis and binding properties of photoactivable biotin-conjugated verapamil derivatives for the study of P-170 glycoprotein. Bioorg Med Chem 1999, 7, 9, 1873.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	12573	3-Bromo-1-propanol; 3-Bromopropanol	627-18-9	C₃H₇BrO	详情	详情
(B)	19490	3-chloro-1-propanol	627-30-5	C₃H₇ClO	详情	详情
(I)	25857	2-(3,4-dimethoxyphenyl)acetonitrile	93-17-4	C₁₀H₁₁NO₂	详情	详情
(II)	42244	2-(3,4-dimethoxyphenyl)-5-hydroxypentanenitrile		C₁₃H₁₇NO₃	详情	详情
(III)	42245	5-chloro-2-(3,4-dimethoxyphenyl)-2-(3-hydroxypropyl)pentanenitrile		C₁₆H₂₂ClNO₃	详情	详情
(IV)	42249	5-[(2-azidophenethyl)(methyl)amino]-2-(3,4-dimethoxyphenyl)-2-(3-hydroxypropyl)pentanenitrile		C₂₅H₃₃N₅O₃	详情	详情
(V)	42250	1-([5-[(3aS,4S,6aR)-3a,4,6a-trimethyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]oxy)-2,5-pyrrolidinedione		C₁₇H₂₅N₃O₅S	详情	详情
(VI)	42246	2-azidophenethylamine; 2-(2-azidophenyl)-1-ethanamine		C₈H₁₀N₄	详情	详情
(VII)	42247	N-(2-azidophenethyl)-2,2,2-trifluoroacetamide		C₁₀H₉F₃N₄O	详情	详情
(VIII)	42248	N-(2-azidophenethyl)-N-methylamine; 2-(2-azidophenyl)-N-methyl-1-ethanamine		C₉H₁₂N₄	详情	详情

Extended Information