N-{4-[bis(2-hydroxyethyl)amino]phenyl}-N'-(4-hydroxyphenethyl)urea -Drug Synthesis Database

【结构式】

【分子编号】64079

【品名】N-{4-[bis(2-hydroxyethyl)amino]phenyl}-N'-(4-hydroxyphenethyl)urea

【CA登记号】

【分子式】C₁₉H₂₅N₃O₄

【分子量】359.42532

【元素组成】C 63.49% H 7.01% N 11.69% O 17.81%

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)

Coupling of tyramine (I) with p-nitrophenyl isocyanate (II) affords urea (III). Subsequent nitro group reduction with H2 and Pd/C gives amine (IV). Condensation of amine (IV) with ethylene oxide (V) leads to the bis-hydroxyethyl amine (VI). This is finally chlorinated employing SOCl2 in pyridine. Alternatively, amine (IV) is subjected to reductive alkylation with chloroacetaldehyde and NaBH3CN to furnish the target bis-chloroethyl amine. (1,2)

参考文献中间体

合成目标

【1】 Jordan, A.M.; Khan, T.H.; Malkin, H.; Osborn, H.M.I.; Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT). Bioorg Med Chem 2002, 10, 8, 2625.
【2】 Riley, P.A.; Photiou, A.; Khan, T.H.; Osborn, H.M.I.; Malkin, H.; Phenylethylamine derivs. and their use in the treatment of melanoma. EP 1303481; WO 0208174 .

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)	19988	4-(2-Aminoethyl)phenol; Tyramine	51-67-2	C₈H₁₁NO	详情	详情
(II)	14909	1-isocyanato-4-nitrobenzene; 4-Nitrophenyl isocyanate	100-28-7	C₇H₄N₂O₃	详情	详情
(III)	64077	N-(4-hydroxyphenethyl)-N'-(4-nitrophenyl)urea		C₁₅H₁₅N₃O₄	详情	详情
(IV)	64078	N-(4-aminophenyl)-N'-(4-hydroxyphenethyl)urea		C₁₅H₁₇N₃O₂	详情	详情
(V)	10393	Oxirane; Ethylene oxide	75-21-8	C₂H₄O	详情	详情
(VI)	64079	N-{4-[bis(2-hydroxyethyl)amino]phenyl}-N'-(4-hydroxyphenethyl)urea		C₁₉H₂₅N₃O₄	详情	详情

Extended Information