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【结 构 式】

【分子编号】50522

【品名】1-(4-nitrophenyl)-3,5-bis(trifluoromethyl)-1H-pyrazole

【CA登记号】

【 分 子 式 】C11H5F6N3O2

【 分 子 量 】325.1701392

【元素组成】C 40.63% H 1.55% F 35.06% N 12.92% O 9.84%

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)

Acid-catalyzed condensation of 4-nitrophenylhydrazine (I) with 1,1,1,5,5,5-hexafluoro-2,4-pentanedione (II) produced pyrazole (III). Reduction of the nitro group of (III) to the corresponding amine (IV) was achieved either by treatment with stannous chloride or by catalytic hydrogenation over Pd/C. Fluoroisonicotinic acid (VI) was prepared by lithiation of 3-fluoropyridine (V) at -78 C followed by quenching with dry ice. Finally, coupling of acid (VI) with amine (IV) yielded the target amide.

1 Sciotti, R.J.; Wagenaar, F.L.; Zhou, X.; Wiedeman, P.E.; Warrior, U.; Luly, J.R.; Djuric, S.W.; Tu, N.P.; Ba Maung, N.Y.; Madar, D.J.; Gubbins, E.J.; Basha, A. (Abbott Laboratories Inc.); Pyrazole inhibitors of cytokine production. EP 1068187; WO 9951580 .
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) 34400 1-(4-nitrophenyl)hydrazine; 4-Nitrophenylhydrazine 100-16-3 C6H7N3O2 详情 详情
(II) 50521 Hexafluoroacetylacetone; 1,1,1,5,5,5-Hexafluoro-2,4-pentanedione; 1,1,1,5,5,5-Hexafluoroacetylacetonate; 1,1,1,5,5,5-Hexafluoroacetylacetone; 1,1,1-Hexafluoro-2,4-pentanedione 1522-22-1 C5H2F6O2 详情 详情
(III) 50522 1-(4-nitrophenyl)-3,5-bis(trifluoromethyl)-1H-pyrazole C11H5F6N3O2 详情 详情
(IV) 50523 4-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]phenylamine; 4-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]aniline C11H7F6N3 详情 详情
(V) 46855 3-fluoropyridine 372-47-4 C5H4FN 详情 详情
(VI) 50524 3-fluoroisonicotinic acid C6H4FNO2 详情 详情
Extended Information