【结 构 式】 |
【分子编号】12998 【品名】2-Chloro-N,N-dimethylacetamide 【CA登记号】2675-89-0 |
【 分 子 式 】C4H8ClNO 【 分 子 量 】121.56636 【元素组成】C 39.52% H 6.63% Cl 29.16% N 11.52% O 13.16% |
合成路线1
该中间体在本合成路线中的序号:(II)By esterification of 2-(2-methyl-5H-[1]-benzopyrano[2,3-b]pyridin-7-yl)propionic acid (I) with 2-chloro-N,N-dimethylacetamide (II) by means of K2CO3 in hot DMF.
【1】 Oe, T.; Kawasaki, K.; Terasawa, M.; Imayoshi, T. (Japan Tobacco Inc.; Welfide Corporation); Benzopyranopyridine acid ester cpds. and their pharmaceutical uses. EP 0284069; JP 1989025782; US 4808593 . |
【2】 Imayoshi, T.; Terasawa, M.; Kawasaki, K.; Oe, T.; Yamada, I.; Yasunaga, Y.; Goto, K.; Tsuruda, M.; Synthesis, pharmacological activity and biopharmaceutical characteristics of alpha,2-dimethyl-5H-[1]benzopyrano[2,3-d]pyridine-7-acetates. Yakugaku Zasshi 1989, 109, 11, 827. |
【3】 Castaner, J.; Prous, J.; Y-23023. Drugs Fut 1992, 17, 6, 469. |
合成路线2
该中间体在本合成路线中的序号:(XXVIII)The optically pure (S)-amine (XXIII) was prepared as follows: Demethylation of the previously described (S)-7-methoxy-1,2,3,4-tetrahydronaphth-2-ylamine (XXVI) in concentrated HBr under reflux gave the amino naphthol (VII). After protection of the amino group of (VII) as the N-Boc derivative (XXVII), the phenolic hydroxyl was alkylated with 2-chloro-N,N-dimethylacetamide (XXVIII) to give (XXIX). Then, Boc group cleavage in (XXIX) by means of HCl in isopropanol furnished the intermediate amine (XXIII).
【1】 Yanagi, T.; et al.; The practical synthesis of a uterine relaxant, bis (2-{[2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide)sulfate (KUR-1246). Chem Pharm Bull 2001, 49, 8, 1018. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VII) | 32819 | (7S)-7-amino-5,6,7,8-tetrahydro-2-naphthalenol | C10H13NO | 详情 | 详情 | |
(XXIII) | 50691 | 2-[[(7S)-7-amino-5,6,7,8-tetrahydro-2-naphthalenyl]oxy]-N,N-dimethylacetamide | C14H20N2O2 | 详情 | 详情 | |
(XXVI) | 32820 | (2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthalenylamine; (2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthalenamine | C11H15NO | 详情 | 详情 | |
(XXVII) | 32821 | tert-butyl (2S)-7-hydroxy-1,2,3,4-tetrahydro-2-naphthalenylcarbamate | C15H21NO3 | 详情 | 详情 | |
(XXVIII) | 12998 | 2-Chloro-N,N-dimethylacetamide | 2675-89-0 | C4H8ClNO | 详情 | 详情 |
(XXIX) | 50694 | tert-butyl (2S)-7-[2-(dimethylamino)-2-oxoethoxy]-1,2,3,4-tetrahydro-2-naphthalenylcarbamate | C19H28N2O4 | 详情 | 详情 |