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【结 构 式】 
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【分子编号】17148 【品名】4-Hydrazinobenzenesulfonamide; 4-Sulfonamidophenylhydrazine 【CA登记号】4392-54-5 |
【 分 子 式 】C6H9N3O2S 【 分 子 量 】187.22248 【元素组成】C 38.49% H 4.85% N 22.44% O 17.09% S 17.13% |
合成路线1
该中间体在本合成路线中的序号：(III)Claisen condensation of 4'-chloroacetophenone (I) with ethyl trifluoroacetate in the presence of NaOMe provided diketone (II). Subsequent reaction of (II) with 4-sulfamoylphenylhydrazine (III) provided the title 1,5-diaryl pyrazole along with minor amounts of the 1,3-diaryl regioisomer, which was removed by recrystallization from EtOAc and isooctane.
| 【1】 Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; et al.; Synthesis and biological evaluation of the 1, 5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, celecoxib). J Med Chem 1997, 40, 9, 1347. |
| 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) | 12685 | 4-Chloroacetophenone; 1-(4-Chlorophenyl)-1-ethanone; p-Chloroacetophenone | 99-91-2 | C8H7ClO | 详情 | 详情 |
| (II) | 38969 | 1-(4-chlorophenyl)-4,4,4-trifluoro-1,3-butanedione | C10H6ClF3O2 | 详情 | 详情 | |
| (III) | 17148 | 4-Hydrazinobenzenesulfonamide; 4-Sulfonamidophenylhydrazine | 4392-54-5 | C6H9N3O2S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)The condensation of 4-methylacetophenone (I) with ethyl trifluoroacetate (II) by means of NaOMe in refluxing methanol gives 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione, which is cyclized with 4-hydrazinophenylsulfonamide (III) in refluxing ethanol.
| 【1】 Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; et al.; Synthesis and biological evaluation of the 1, 5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, celecoxib). J Med Chem 1997, 40, 9, 1347. |
| 【2】 Graul, A.; Martel, A.M.; Castañer, J.; Celecoxib. Drugs Fut 1997, 22, 7, 711. |
| 【3】 Talley, J.J.; Penning, T.D.; Collins, P.W.; Rogier, D.J. Jr.; Malecha, J.W.; Miyashiro, J.M.; Bertenshaw, S.R.; Khanna, I.K.; Granets, M.J.; Rogers, R.S.; Carter, J.S.; Docter, S.H.; Yu, S.S. (Pharmacia Corp.); Substd. pyrazolyl benzenesulfonamides for the treatment of inflammation. EP 0731795; EP 0922697; EP 0924201; JP 1997506350; JP 2000109466; US 5521207; WO 9515316 . |
| 【4】 Zhi, B.; Newaz, M.; Talley, J.J.; Bertenshaw, S. (Pharmacia Corp.); Method of preparing 3-haloalkyl-1H-pyrazoles. WO 9637476 . |
| 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) | 17145 | 1-(4-methylphenyl)-1-ethanone; p-methylacetophenone; 4-methylacetophenone; 4-methylphenylethanone | 122-00-9 | C9H10O | 详情 | 详情 |
| (II) | 14588 | Ethyl 2,2,2-trifluoroacetate; Trifluoroethyl acetate | 383-63-1 | C4H5F3O2 | 详情 | 详情 |
| (III) | 17147 | 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione; 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione | 720-94-5 | C11H9F3O2 | 详情 | 详情 |
| (IV) | 17148 | 4-Hydrazinobenzenesulfonamide; 4-Sulfonamidophenylhydrazine | 4392-54-5 | C6H9N3O2S | 详情 | 详情 |