4-([[4-(acetamido)-1-methyl-1H-imidazol-2-yl]carbonyl]amino)-1-methyl-1H-pyrrole-2-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】50160

【品名】4-([[4-(acetamido)-1-methyl-1H-imidazol-2-yl]carbonyl]amino)-1-methyl-1H-pyrrole-2-carboxylic acid

【CA登记号】

【分子式】C₁₃H₁₅N₅O₄

【分子量】305.2934

【元素组成】C 51.15% H 4.95% N 22.94% O 20.96%

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：(I)

The pyrrolecarboxylic acid derivative (I) was treated with BOP reagent, and the resulting hydroxybenzotriazolyl ester was reduced in situ with NaBH4 to furnish alcohol (II). Oxidation of (II) by means of activated MnO2 produced aldehyde (III). Wadsworth-Emmons reaction of aldehyde (III) with triethylphosphonoacetate gave rise to the unsaturated ester (IV). After basic hydrolysis of the ester group of (IV), the resultant carboxylic acid (V) was activated as the imidazolide (VI) upon treatment with carbonyldiimidazole. This was finally coupled with the segment A of DU86 (VII) in the presence of NaH in DMF at low temperature to yield the target amide.

参考文献中间体

合成目标

【1】 Tao, Z.-F.; et al.; Highly cooperative DNA dialkylation by the homodimer of imidazole - Pyrrole diamide - CPI conjugate with vinyl linker. J Am Chem Soc 2000, 122, 8, 1602.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	50160	4-([[4-(acetamido)-1-methyl-1H-imidazol-2-yl]carbonyl]amino)-1-methyl-1H-pyrrole-2-carboxylic acid	C₁₃H₁₅N₅O₄	详情	详情
(II)	50161	4-(acetamido)-N-[5-(hydroxymethyl)-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-imidazole-2-carboxamide	C₁₃H₁₇N₅O₃	详情	详情
(III)	50162	4-(acetamido)-N-(5-formyl-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-imidazole-2-carboxamide	C₁₃H₁₅N₅O₃	详情	详情
(IV)	50163	ethyl (E)-3-[4-([[4-(acetamido)-1-methyl-1H-imidazol-2-yl]carbonyl]amino)-1-methyl-1H-pyrrol-2-yl]-2-propenoate	C₁₇H₂₁N₅O₄	详情	详情
(V)	50164	(E)-3-[4-([[4-(acetamido)-1-methyl-1H-imidazol-2-yl]carbonyl]amino)-1-methyl-1H-pyrrol-2-yl]-2-propenoic acid	C₁₅H₁₇N₅O₄	详情	详情
(VI)	50165	4-(acetamido)-N-[5-[(E)-3-(1H-imidazol-1-yl)-3-oxo-1-propenyl]-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-imidazole-2-carboxamide	C₁₈H₁₉N₇O₃	详情	详情
(VII)	38365	methyl (3bR,4aS)-2-methyl-8-oxo-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate	C₁₄H₁₄N₂O₃	详情	详情

Extended Information