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【结 构 式】

【分子编号】24278

【品名】3-(methylamino)propanenitrile

【CA登记号】693-05-0

【 分 子 式 】C4H8N2

【 分 子 量 】84.121

【元素组成】C 57.11% H 9.59% N 33.3%

与该中间体有关的原料药合成路线共 4 条

合成路线1

该中间体在本合成路线中的序号:(IV)

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:(IV)

 

1 Joshi NS,Ramarn BP, Rao KS, et aL 2006. Processes for the preparation of alfuzosin and salts thereof and novel crystalline forms of alfuzosin W0 2006090268
2 Manoury PM, Binet JL, Dumas AP, et al.1986. Synthesis and antihypertensive activity of aseries of 4.amino-6,7-dimethoxyquinazoline derivativesJ Med Chem,29 1 19~25 Manoury PM, Binet JL, Dumas AP, et al.1986. Synthesis and antihypertensive activity of aseries of 4.amino-6,7-dimethoxyquinazoline derivativesJ Med Chem,29 1 19~25
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
(IV) 24278 3-(methylamino)propanenitrile 693-05-0 C4H8N2 详情 详情
(VIII) 66068 N-(4-AMINO-6,7-DIMETHOXYQUINAZOL-2-YL)-N-METHYL-2-CYANOETHYLAMINE 76362-28-2 C14H17N5O2 详情 详情
(IX) 66069 N2-(3-aminopropyl)-6,7-dimethoxy-N2-methylquinazoline-2,4-diamine   C14H21N5O2 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
(XI) 66071 Tetrahydro-2-furancarbonyl chloride 52449-98-6 C5H7ClO2 详情 详情

合成路线3

该中间体在本合成路线中的序号:(IV)

 

1 Sadanand NS, Bhivsan AP, Chandrakantno JU, 2007.Preparation of alfuzosin. US 2007105880 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007
2 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007 Manoury PM 1982.4-Amino-6,7-dimetboxyquinazol-2-yl alkylenediamines US 4315007
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
(IV) 24278 3-(methylamino)propanenitrile 693-05-0 C4H8N2 详情 详情
(VIII) 66068 N-(4-AMINO-6,7-DIMETHOXYQUINAZOL-2-YL)-N-METHYL-2-CYANOETHYLAMINE 76362-28-2 C14H17N5O2 详情 详情
(IX) 66069 N2-(3-aminopropyl)-6,7-dimethoxy-N2-methylquinazoline-2,4-diamine   C14H21N5O2 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
(XII) 52096 Tetrahydrofuran-2-carboxylic Acid; 2-Tetrahydrofuroic acid 16874-33-2 C5H8O3 详情 详情

合成路线4

该中间体在本合成路线中的序号:(III)

 

1 Pulla Reddy M.2007. Improved process for the preparation of ibandronate sodium. W0 2007013097[本专利为Natco Pharma Ltd(IN)所有]
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) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(II) 11021 Methanamine; Methylamine 74-89-5 CH5N 详情 详情
(III) 24278 3-(methylamino)propanenitrile 693-05-0 C4H8N2 详情 详情
(IV) 66461 3-(methyl(pentyl)amino)propanenitrile   C9H18N2 详情 详情
(V) 15769 3-[methyl(pentyl)amino]propionic acid C9H19NO2 详情 详情
Extended Information