N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxamide -Drug Synthesis Database

【结构式】

【分子编号】25330

【品名】N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxamide

【CA登记号】

【分子式】C₂₀H₂₅N₃O₃

【分子量】355.43692

【元素组成】C 67.58% H 7.09% N 11.82% O 13.5%

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：(VII)

Pyrroline (III) was prepared by Favorskii rearrangement of 3,5-dibromo-2,2,6,6-tetramethylpiperidinone (I) in the presence of 1,3-diaminopropane (II). Acylation at the primary amino group of (III) with phthalic anhydride (IV) gave the 2-carboxybenzamide (VI), which was cyclized to the target phthalimide (VII) by refluxing in toluene in the presence of Et3N. Alternatively, the phthalimido derivative (VII) was obtained by condensation of amine (III) with phthalimide (V) at 150 C. The target compound was then isolated as the hydrochloride salt upon treatment with HCl in EtOH-Et2O.

参考文献中间体

合成目标

【1】 Bodi, I.; Csak, J.; Frank, L.; Hankovszky, O.H.; Hideg, K. (Alkaloida Chemical Co. Ltd.); New alkyl diamine derivatives. EP 0134225; JP 1985500669; US 4703056; US 5028609; US 5032600; WO 8402907 .

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)	25327	3,5-dibromo-2,2,6,6-tetramethyl-4-piperidinone	57167-75-6	C₉H₁₅Br₂NO	详情	详情
(II)	19331	3-aminopropylamine; 1,3-propanediamine	109-76-2	C₃H₁₀N₂	详情	详情
(III)	25328	N-(3-aminopropyl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxamide		C₁₂H₂₃N₃O	详情	详情
(IV)	11900	2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride	85-44-9	C₈H₄O₃	详情	详情
(V)	12376	Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione	85-41-6	C₈H₅NO₂	详情	详情
(VI)	25329	2-[[(3-[[(2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)carbonyl]amino]propyl)amino]carbonyl]benzoic acid		C₂₀H₂₇N₃O₄	详情	详情
(VII)	25330	N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxamide		C₂₀H₂₅N₃O₃	详情	详情

Extended Information