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【结 构 式】 
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【分子编号】17224 【品名】5-(3-fluorophenyl)-2-methyl-4-phenyl-1,3-oxazole 【CA登记号】 |
【 分 子 式 】C16H12FNO 【 分 子 量 】253.2758232 【元素组成】C 75.88% H 4.78% F 7.5% N 5.53% O 6.32% |
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：(V)The condensation of cyclohexanecarbonyl chloride (I) with 3-fluorobenzyl bromide (II) by means of tetrakis(triphenylphosphine)palladium and Zn in dimethoxyethane gives the ethanone (III), which is treated with lead tetraacetate in acetic acid, yielding the alpha-acetoxyethanone (IV). The cyclization of (IV) with ammonium acetate in refluxing acetic acid affords the oxazole derivative (V), which is treated with chlorosulfonic acid at 100 C, yielding the 4-chlorosulfonyl derivative (VI). Finally, this compound is amidated with ammonia in THF/water.
| 【1】 Hashimoto, H.; et al.; 4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors: Enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522. J Med Chem 2002, 45, 7, 1511. |
| 【2】 Silvestre, J.S.; Leeson, P.A.; Castañer, J.; JTE-522. Drugs Fut 1998, 23, 6, 598. |
| 【3】 Haruta, J.; Hashimoto, H.; Matsushita, M. (Japan Tobacco Inc.); Heteroaromatic oxazole cpds. and use thereof. EP 0745596; EP 0826676; JP 1996325249; JP 1997052882; US 5994381; WO 9619462; WO 9619463 . |
| 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) | 17220 | cyclohexanecarbonyl chloride; Cyclohexanecarboxylic acid chloride | 2719-27-9 | C7H11ClO | 详情 | 详情 |
| (II) | 17221 | 3-Fluorobenzyl bromide; 1-(bromomethyl)-3-fluorobenzene | 456-41-7 | C7H6BrF | 详情 | 详情 |
| (III) | 17222 | 1-cyclohexyl-2-(3-fluorophenyl)-1-ethanone | C14H17FO | 详情 | 详情 | |
| (IV) | 17223 | 2-cyclohexyl-1-(3-fluorophenyl)-2-oxoethyl acetate | C16H19FO3 | 详情 | 详情 | |
| (V) | 17224 | 5-(3-fluorophenyl)-2-methyl-4-phenyl-1,3-oxazole | C16H12FNO | 详情 | 详情 |
Extended Information