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【结 构 式】 
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【分子编号】61122 【品名】3-bromo-N,N-dimethyl-1-propanamine; N-(3-bromopropyl)-N,N-dimethylamine 【CA登记号】 |
【 分 子 式 】C5H12BrN 【 分 子 量 】166.06102 【元素组成】C 36.16% H 7.28% Br 48.12% N 8.43% |
合成路线1
该中间体在本合成路线中的序号：(VIII)It can be prepared in several different way (Scheme 31229302a): 1) The nitrosation of 2-[3-(dimethylamino)propylamino]-5-methylbenzophenone (I) with NaNO2 and HCl in chloroform gives the corresponding N-nitroso compound (II), which is cyclized by reaction with Zn in acetic acid. 2) By reaction of 1-(3-methylaminopropyl)-5-methyl-3-phenyl-1H-indazole (III) with formaldehyde and NaBH4 in methanol. 3) The reaction of 3-phenyl-5-methyl-1H-indazole (IV) with 1,3-dibromopropane (V) by means of NaH in DMF gives 1-(3-bromopropyl)-5-methyl-3-phenyl-1H-indazole (VI), which is then condensed with dimethylamine (VII). 4) By reaction of (IV) with 1-(dimethylamino)-3-bromopropane (VIII) by means of NaOH in a mixture of toluene and water.
| 【1】 Fujimura, Y.; et al. (Cubist Pharmaceuticals, Inc.); JP 76125281 . |
| 【2】 Fujimura, Y.; et al. (Chugai Pharmaceutical Co. Ltd.); DE 2503815; FR 2259601; GB 1489280; JP 75106958; JP 75145244; JP 75148335; JP 7663172; US 3994890 . |
| 【3】 Fujimura, Y.; et al. (Chugai Pharmaceutical Co. Ltd.); JP 7659861 . |
| 【4】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Paton, D.M.; FS-32. Drugs Fut 1979, 4, 8, 583. |
| 【5】 Fujimura, Y.; et al. (Chugai Pharmaceutical Co. Ltd.); JP 7714765 . |
| 【6】 Fujimura, Y.; et al. (Chugai Pharmaceutical Co. Ltd.); JP 7714766 . |
| 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) | 61119 | (2-{[3-(dimethylamino)propyl]amino}-5-methylphenyl)(phenyl)methanone | C19H24N2O | 详情 | 详情 | |
| (II) | 61120 | C19H23N3O2 | 详情 | 详情 | ||
| (III) | 61123 | N-methyl-3-(5-methyl-3-phenyl-1H-indazol-1-yl)-1-propanamine; N-methyl-N-[3-(5-methyl-3-phenyl-1H-indazol-1-yl)propyl]amine | C18H21N3 | 详情 | 详情 | |
| (IV) | 34172 | 5-methyl-3-phenyl-1H-indazole | C14H12N2 | 详情 | 详情 | |
| (V) | 12581 | 1,3-Dibromopropane | 109-64-8 | C3H6Br2 | 详情 | 详情 |
| (VI) | 61121 | 1-(3-bromopropyl)-5-methyl-3-phenyl-1H-indazole | C17H17BrN2 | 详情 | 详情 | |
| (VII) | 19443 | N-methylmethanamine; N,N-dimethylamine | 124-40-3 | C2H7N | 详情 | 详情 |
| (VIII) | 61122 | 3-bromo-N,N-dimethyl-1-propanamine; N-(3-bromopropyl)-N,N-dimethylamine | C5H12BrN | 详情 | 详情 |