3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】53390

【品名】3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl chloride

【CA登记号】n/a

【分子式】C₁₁H₈ClNO₃

【分子量】237.64216

【元素组成】C 55.6% H 3.39% Cl 14.92% N 5.89% O 20.2%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

Acylation of phenethylamine (III) with acid chloride (II), prepared from phthalimidopropionic acid (I) and SOCl2, gave amide (IV). Subsequent Bischler-Napieralski cyclization of amide (IV) in the presence of POCl3 and P2O5 produced the corresponding dihydroisoquinoline, which was isolated as the hydrochloride salt (V). Catalytic hydrogenation of (V) using PtO2 afforded the tetrahydroisoquinoline (VI). After protection of (VI) as the N-Boc derivative (VII), the primary amine (VIII) was liberated by phthaloyl group hydrazinolysis. Coupling of amine (VIII) with nicotinic acid (IX) employing EDC and HOBt yielded the nicotinamide compound (X). Subsequent acidic cleavage of the Boc protecting group of (X) provided amine (XI), which was finally acylated with 4-butylbenzenesulfonyl chloride (XII) in the presence of resin-bound piperidine to furnish the target sulfonamide.

参考文献中间体

合成目标

【1】 Barn, D.R.; et al.; Parallel synthesis and biological activity of a new class of high affinity and selective delta-opioid ligand. Bioorg Med Chem 2001, 9, 10, 2609.

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)	53389	3-Phthalimidopropionic acid; Phthalyl-beta-alanine	3339-73-9	C₁₁H₉NO₄	详情	详情
(II)	53390	3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl chloride	n/a	C₁₁H₈ClNO₃	详情	详情
(III)	18333	Phenethylamine; 2-Phenyl-1-ethanamine	64-04-0	C₈H₁₁N	详情	详情
(IV)	53391	3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-phenethylpropanamide	n/a	C₁₉H₁₈N₂O₃	详情	详情
(V)	53392	2-[2-(3,4-dihydro-1-isoquinolinyl)ethyl]-1H-isoindole-1,3(2H)-dione	n/a	C₁₉H₁₆N₂O₂	详情	详情
(VI)	53393	2-[2-(1,2,3,4-tetrahydro-1-isoquinolinyl)ethyl]-1H-isoindole-1,3(2H)-dione	n/a	C₁₉H₁₈N₂O₂	详情	详情
(VII)	53394	tert-butyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate	n/a	C₂₄H₂₆N₂O₄	详情	详情
(VIII)	53395	tert-butyl 1-(2-aminoethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate	n/a	C₁₆H₂₄N₂O₂	详情	详情
(IX)	10752	Nicotinic acid; Niacin	59-67-6	C₆H₅NO₂	详情	详情
(X)	53396	tert-butyl 1-{2-[(3-pyridinylcarbonyl)amino]ethyl}-3,4-dihydro-2(1H)-isoquinolinecarboxylate	n/a	C₂₂H₂₇N₃O₃	详情	详情
(XI)	53397	N-[2-(1,2,3,4-tetrahydro-1-isoquinolinyl)ethyl]nicotinamide	n/a	C₁₇H₁₉N₃O	详情	详情
(XII)	53398	4-n-Butylbenzenesulphonyl chloride	54997-92-1	C₁₀H₁₃ClO₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

3-Phthalimidopropionyl chloride (I) is condensed with n-nonylamine to produce the corresponding amide (II). Subsequent hydrazinolysis of phthalimide (II) furnishes the aminopropanamide (III), which is condensed with D-pantonolactone (IV) to yield the desired compound.

参考文献中间体

合成目标

【1】 Clifton, G.; Bryant, S.R.; Skinner, C.G.; N1-(Substituted) pantothenamides, antimetabolites of pantothenic acid. Arch Biochem Biophys 1970, 137, 2, 523.

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)	53390	3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl chloride	n/a	C₁₁H₈ClNO₃	详情	详情
(II)	64801	3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-nonylpropanamide		C₂₀H₂₈N₂O₃	详情	详情
(III)	64802	3-amino-N-nonylpropanamide		C₁₂H₂₆N₂O	详情	详情
(IV)	51427	D-Pantolactone; R(-)-2-Hydroxy-3,3-dimethyl-gamma-butyrolactone	599-04-2	C₆H₁₀O₃	详情	详情

Extended Information