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【结 构 式】

【分子编号】27871

【品名】1-[(1R,2R)-2-(2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one

【CA登记号】

【 分 子 式 】C23H20F5N5O3

【 分 子 量 】509.435716

【元素组成】C 54.23% H 3.96% F 18.65% N 13.75% O 9.42%

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:(XVI)

Treatment of epoxyalcohol (IX) with trifluoromethanesulfonic anhydride and diisopropyl ethylamine gave triflate (XIII). Condensation of (XIII) with imidazolone (IV) provided the required N-alkylated compound (XIV) along with some O-alkylated isomer, which were separated by column chromatography. Epoxide opening with triazole (XV) afforded the imidazolone (XVI), which was finally hydrogenated to produce the target imidazolidinone. Alternatively, condensation of triflate (XIII) with imidazolidinone (V) furnished, after chromatographic separation of some O-alkylated isomer, imidazolidinone (XVII). Finally, the reaction of (XVII) with triazole (XV) then provided an alternative route to the target compound.

1 Itoh, K.; Tamura, N.; Matsushita, Y.; Hososno, H.; Hayashi, R.; Okonogi, K.; Kitazaki, T.; Tasaka, A.; Optically active antifungal azoles. VIII. Synthesis and antifungal activity of 1-[(1R,2R)-2-(2,4-difluoro- and 2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-substituted phenyl)-2(1H,3H)-imidazolones and 2-imidazolidinones. Chem Pharm Bull 1999, 47, 3, 351.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 27860 1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one C11H8F4N2O2 详情 详情
(V) 27861 1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2-imidazolidinone C11H10F4N2O2 详情 详情
(IX) 27865 (1S)-1-[(2R)-2-(2-fluorophenyl)oxiranyl]-1-ethanol C10H11FO2 详情 详情
(XIII) 27869 (1S)-1-[(2R)-2-(2-fluorophenyl)oxiranyl]ethyl trifluoromethanesulfonate C11H10F4O4S 详情 详情
(XIV) 27870 1-[(1R)-1-[(2S)-2-(2-fluorophenyl)oxiranyl]ethyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one C21H17F5N2O3 详情 详情
(XV) 13135 1H-1,2,4-Triazole; 1,2,4-Triazole 288-88-0 C2H3N3 详情 详情
(XVI) 27871 1-[(1R,2R)-2-(2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one C23H20F5N5O3 详情 详情
(XVII) 27872 1-[(1R)-1-[(2S)-2-(2-fluorophenyl)oxiranyl]ethyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2-imidazolidinone C21H19F5N2O3 详情 详情
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