methyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)propanoate -Drug Synthesis Database

【结构式】

【分子编号】44315

【品名】methyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)propanoate

【CA登记号】

【分子式】C₂₃H₂₄Br₂N₄O₅

【分子量】596.27552

【元素组成】C 46.33% H 4.06% Br 26.8% N 9.4% O 13.42%

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：(III)

Condensation between 3,5-dibromotyrosine methyl ester (I) and 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine (II) in the presence of carbonyl ditriazole (CDT) furnished the asymmetric urea (III). Subsequent hydrolysis of the ester group using LiOH provided carboxylic acid (IV). This was finally coupled with N-phenylpiperazine (V) employing O-benzotriazolyl-N,N,N',N'-tetramethyluronium tetrafluoroborate and 1-hydroxybenzotriazole to yield the corresponding amide.

参考文献中间体

合成目标

【1】 Eberlein, W.; Wienen, W.; Doods, H.; Rudolf, K.; Entzeroth, M.; Pieper, H.; Engel, W.; Hallermayer, G. (Dr. Karl Thomae GmbH); Modified aminoacids, pharmaceuticals containing these cpds. and methods for their production. JP 2000505100; WO 9811128 .

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)	44314	methyl 2-amino-3-(3,5-dibromo-4-hydroxyphenyl)propanoate		C₁₀H₁₁Br₂NO₃	详情	详情
(II)	12138	1-(4-Piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one; 4-(2-Keto-1-benzimidazolinyl)piperidine	20662-53-7	C₁₂H₁₅N₃O	详情	详情
(III)	44315	methyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)propanoate		C₂₃H₂₄Br₂N₄O₅	详情	详情
(IV)	44316	3,5-dibromo-4-hydroxy-N-[[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]phenylalanine		C₂₂H₂₂Br₂N₄O₅	详情	详情
(V)	10756	N-Phenylpiperazine; 1-Phenylpiperazine; Phenyl piperazine	92-54-6	C₁₀H₁₄N₂	详情	详情

Extended Information