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【结 构 式】

【分子编号】24280

【品名】N-[3-(methylamino)propyl]tetrahydro-2-furancarboxamide;Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide;Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide;2-Furancarboxamide,tetrahydro-N-[3-(methylamino)propyl]-

【CA登记号】81403-67-0

【 分 子 式 】C9H18N2O2

【 分 子 量 】186.2542

【元素组成】C 58.04% H 9.74% N 15.04% O 17.18%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

Title compound can be prepared as follows: 1) 6,7-Dimethoxyquinazolin-2,4-dione (I) is converted to 2,4-dichloro 6,7-dimethoxyquinazoline (II), followed by selective displacement of the 4-chloro group with ammonia to give 4-amino-2-chloro-6,7-dimethoxyquinazoline (III). 2) 3-(Methylamino)propanenitrile (IV) is reacted with the mixed anhydride obtained from tetrahydrofuran-2-carboxylic acid and ethyl chloroformate to form the amide (V), which on hydrogenation over rhodium at 80 C in the presence of ammonia affords the required secondary amine (VI) via rearrangement of the initially formed primary amine (VII). Condensation of amine (VI) with 4-amino-2-chloro-6,7-dimethoxyquinazoline (III) in refluxing amyl alcohol gives alfuzosin hydrochloride.

1 Binet, J.L.; Manoury, P.M.; Dumas, A.P.; Lefevre-Borg, F.; Cavero, I.; Synthesis and antihypertensive activity of a series of 4-amino-6,7-dimethoxyquinazoline derivatives. J Med Chem 1986, 29, 19-25.
2 Cazor, J.L.; Borg, F.; Dimsdale, M.; Alfuzosin hydrochloride. Drugs Fut 1986, 11, 10, 821.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
62978   C8H12O5 详情 详情
(I) 24275 6,7-Dimethoxy-2,4(1H,3H)-quinazolinedione; 6,7-Dimethoxyquinazoline-2,4-dione 28888-44-0 C10H10N2O4 详情 详情
(II) 24276 2,4-dichloro-6-methoxy-7-quinazolinyl methyl ether 27631-29-4 C10H8Cl2N2O2 详情 详情
(III) 10443 2-Chloro-6,7-dimethoxy-4-quinazolinamine; 4-Amino-2-chloro-6,7-dimethoxyquinazoline; 2-Chloro-6,7-dimethoxy-4-quinazolinylamine 23680-84-4 C10H10ClN3O2 详情 详情
(IV) 24278 3-(methylamino)propanenitrile 693-05-0 C4H8N2 详情 详情
(V) 24279 N-(2-cyanoethyl)-N-methyltetrahydro-2-furancarboxamide C9H14N2O2 详情 详情
(VI) 24280 N-[3-(methylamino)propyl]tetrahydro-2-furancarboxamide;Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide;Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide;2-Furancarboxamide,tetrahydro-N-[3-(methylamino)propyl]- 81403-67-0 C9H18N2O2 详情 详情
(VII) 24281 N-(3-aminopropyl)-N-methyltetrahydro-2-furancarboxamide C9H18N2O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XXIII)

 

1 Anumula RR.Alla S,Gilla G.et al.2007.Process for preoration alfuzosin Via esterification oftetra-hydro-2-furoic acid followed by coupling with N-methrd-l,3-propanediamine, US 2007066824
2 Hu GY,Xiang HL,Xu LML 2007.PrepantionofaKuzosin发明专利申请公开说明书,CN 1935806
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 10443 2-Chloro-6,7-dimethoxy-4-quinazolinamine; 4-Amino-2-chloro-6,7-dimethoxyquinazoline; 2-Chloro-6,7-dimethoxy-4-quinazolinylamine 23680-84-4 C10H10ClN3O2 详情 详情
(X) 66070 N-(3-((4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino)propyl)tetrahydrofuran-2-carboxamide   C19H27N5O4 详情 详情
(XXIII) 24280 N-[3-(methylamino)propyl]tetrahydro-2-furancarboxamide;Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide;Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide;2-Furancarboxamide,tetrahydro-N-[3-(methylamino)propyl]- 81403-67-0 C9H18N2O2 详情 详情
Extended Information