【结 构 式】 |
【分子编号】60456 【品名】4-fluoro-N-(4-nitrophenyl)benzamide 【CA登记号】 |
【 分 子 式 】C13H9FN2O3 【 分 子 量 】260.2245432 【元素组成】C 60% H 3.49% F 7.3% N 10.77% O 18.44% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号:(III)Acylation of 4-nitroaniline (I) with 4-fluorobenzoyl chloride (II) affords benzanilide (III). Catalytic hydrogenation of the nitro group of (III) employing Pt/C then gives amine (IV). Diazotization of (IV), followed by reduction with SnCl2 leads to hydrazine (V). Reaction of 5-chloro-2-pentanone (VI) with dimethylamine yields the amino ketone (VII). Finally, the title compound is obtained by Fisher indole synthesis from aryl hydrazine (V) and ketone (VII) under acidic conditions.
【1】 Xu, Y.-C.; Johnson, K.W.; Phebus, L.A.; et al.; N-[3-(2-Dimethylaminoethyl)-2-methyl-1-H-indol-5-yl]-4-fluorobenzamide: A potent, selective, and orally active 5-HT1F receptor agonist potentially useful for migraine therapy. J Med Chem 2001, 44, 24, 4031. |
【2】 Johnson, K.W.; Phebus, L.A. (Eli Lilly and Company); Use of a serotonin 5-HT1F agonist in the manufacture of a medicament for treating or ameliorating the symptoms of common cold or allergic rhinitis. EP 0824917; US 5962473; WO 9806402 . |
【3】 Fritz, J.E.; Hahn, P.J.; Kaldor, S.W.; Siegel, M.G.; Xu, Y.-C. (Eli Lilly and Company); N-[2-Substd.-3-(2-aminoethyl)-1H-indol-5-yl]-amides: New 5-HT1F agonists. EP 0768301; JP 1999513666; WO 9713512 . |
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) | 15547 | 4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline | 100-01-6 | C6H6N2O2 | 详情 | 详情 |
(II) | 17263 | 4-fluorobenzoyl chloride | 403-43-0 | C7H4ClFO | 详情 | 详情 |
(III) | 60456 | 4-fluoro-N-(4-nitrophenyl)benzamide | C13H9FN2O3 | 详情 | 详情 | |
(IV) | 60457 | N-(4-aminophenyl)-4-fluorobenzamide | C13H11FN2O | 详情 | 详情 | |
(V) | 60458 | 4-fluoro-N-(4-hydrazinophenyl)benzamide | C13H12FN3O | 详情 | 详情 | |
(VI) | 60460 | 5-chloro-2-pentanone | C5H9ClO | 详情 | 详情 | |
(VII) | 60459 | 5-(dimethylamino)-2-pentanone | C7H15NO | 详情 | 详情 |
Extended Information