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【结 构 式】 
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【分子编号】34172 【品名】5-methyl-3-phenyl-1H-indazole 【CA登记号】 |
【 分 子 式 】C14H12N2 【 分 子 量 】208.26276 【元素组成】C 80.74% H 5.81% N 13.45% |
合成路线1
该中间体在本合成路线中的序号：(I)By cyclization of 5-methyl-3-phenylindazole (I) with 1,3-dibromopropane (II) by means of NaH in DMF or triethylbenzylammonium chloride NaOH in toluene - water.
| 【1】 Fujimura, Y.; et al.; Pyrazoloindazole derivatives and bronchodilating composition. EP 0023633; JP 56015287; US 4409234 . |
| 【2】 Sakai, K.; Shiraki, Y.; Pharmacologic potency and selectivity of a new bronchodilator agent, 2,3-dihydro-7-methyl-9-phenyl-1H-pyrazolo[1,2-a]indazolium bromide (FKK) on canine tracheal preparations 'in vivo' and 'in vitro'. Arch Intl Pharmacodyn Ther 1983, 262, 1, 150-163. |
| 【3】 Serradell, M.N.; Castaner, J.; Chu, S.S.; FKK. Drugs Fut 1984, 9, 4, 264. |
合成路线2
该中间体在本合成路线中的序号：(IV)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 |