(2S)-N-(3-aminopropyl)-1-[(2,4-dichloro-3-[[(2,4-dimethyl-8-quinolinyl)oxy]methyl]phenyl)sulfonyl]-2-pyrrolidinecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】37922

【品名】(2S)-N-(3-aminopropyl)-1-[(2,4-dichloro-3-[[(2,4-dimethyl-8-quinolinyl)oxy]methyl]phenyl)sulfonyl]-2-pyrrolidinecarboxamide

【CA登记号】

【分子式】C₂₆H₃₀Cl₂N₄O₄S

【分子量】565.52016

【元素组成】C 55.22% H 5.35% Cl 12.54% N 9.91% O 11.32% S 5.67%

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)

The title compound has been synthesized by condensation of amidino benzoic acid (I) with primary amine (II) using EDC and HOAt.

参考文献中间体

合成目标

【1】 Dodey, P.; Bondoux, M.; Ou, K.; Barth, M.; Houziaux, P. (Fournier Industrie et Santé); Novel N-benzenesulphonyl-L-proline derivs., method for preparing and therapeutic use. EP 0944618; US 6063791; WO 9824783 .

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)	22482	4-Amidinobenzic acid; 4-[amino(imino)methyl]benzoic acid	15535-95-2	C₈H₈N₂O₂	详情	详情
(II)	37922	(2S)-N-(3-aminopropyl)-1-[(2,4-dichloro-3-[[(2,4-dimethyl-8-quinolinyl)oxy]methyl]phenyl)sulfonyl]-2-pyrrolidinecarboxamide		C₂₆H₃₀Cl₂N₄O₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

In an alternative procedure, amine (II) was condensed with 4-cyanobenzoic acid (III) to give amide (IV). Subsequent addition of hydroxylamine to the cyano group of (IV) afforded N-hydroxy amidine (V), which was acetylated with Ac2O to produce (VI). This compound was finally reduced to the target amidine by hydrogenation over Lindlar catalyst.

参考文献中间体

合成目标

【1】 Dodey, P.; Bondoux, M.; Ou, K.; Barth, M.; Houziaux, P. (Fournier Industrie et Santé); Novel N-benzenesulphonyl-L-proline derivs., method for preparing and therapeutic use. EP 0944618; US 6063791; WO 9824783 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	37922	(2S)-N-(3-aminopropyl)-1-[(2,4-dichloro-3-[[(2,4-dimethyl-8-quinolinyl)oxy]methyl]phenyl)sulfonyl]-2-pyrrolidinecarboxamide		C₂₆H₃₀Cl₂N₄O₄S	详情	详情
(III)	36897	4-cyanobenzoic acid；4-Carboxybenzonitrile;p-Carboxybenzonitrile	619-65-8	C₈H₅NO₂	详情	详情
(IV)	37923	(2S)-N-[3-[(4-cyanobenzoyl)amino]propyl]-1-[(2,4-dichloro-3-[[(2,4-dimethyl-8-quinolinyl)oxy]methyl]phenyl)sulfonyl]-2-pyrrolidinecarboxamide		C₃₄H₃₃Cl₂N₅O₅S	详情	详情
(V)	37924	(2S)-N-[3-([4-[amino(hydroxyimino)methyl]benzoyl]amino)propyl]-1-[(2,4-dichloro-3-[[(2,4-dimethyl-8-quinolinyl)oxy]methyl]phenyl)sulfonyl]-2-pyrrolidinecarboxamide		C₃₄H₃₆Cl₂N₆O₆S	详情	详情
(VI)	37925	(2S)-N-[3-([4-[[(acetoxy)imino](amino)methyl]benzoyl]amino)propyl]-1-[(2,4-dichloro-3-[[(2,4-dimethyl-8-quinolinyl)oxy]methyl]phenyl)sulfonyl]-2-pyrrolidinecarboxamide		C₃₆H₃₈Cl₂N₆O₇S	详情	详情

Extended Information