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【结 构 式】

【分子编号】45581

【品名】1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-nitrophenyl)-2-imidazolidinone

【CA登记号】

【 分 子 式 】C21H20F2N6O4

【 分 子 量 】458.4246464

【元素组成】C 55.02% H 4.4% F 8.29% N 18.33% O 13.96%

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:(XLIII)

In a further procedure, epoxide (XXXII) was condensed with ethanolamine (XXXIX) to afford amino diol (XL). Coupling of (XL) with carbamate (IX) produced the N-(hydroxyethyl)urea (XLI). Chlorination of the primary hydroxyl group of (XLI) with POCl3, followed by cyclization in the presence of Et3N, gave rise to the title imidazolidinone. Alternatively, amino diol (XL) was coupled with 4-nitrophenyl isocyanate (XXXV) to give urea (XLII). Chlorination of (XLII), followed by cyclization in the presence of Et3N, produced imidazolidinone (XLIII). The tetrazolyl group of the target compound was then introduced by catalytic hydrogenation of the nitro group of (XLIII), followed by treatment with NaN3 and triethyl orthoformate.

3 Kitazaki, T.; Matsushita, Y.; Hosono, H.; Itoh, K.; Mitsudera, H. (Takeda Chemical Industries, Ltd.); Triazole derivs. and their production. EP 0884311 .
1 Ichikawa, T.; et al.; Optically active antifungal azoles. XI. An alternative synthetic route for 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (TAK-456) and its analog. Chem Pharm Bull 2000, 48, 12, 1947.
2 Ichikawa, T.; Matsushita, Y.; Yamada, M.; Tasaka, A.; Yamaguchi, M.; Itoh, K.; Okonogi, K.; Kitazaki, T.; TAK-456 and the water-soluble prodrug TAK-457, new antifungal triazoles: Synthesis and in vitro antifungal activity. 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1085.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 45560 phenyl 4-(1H-1,2,3,4-tetraazol-1-yl)phenylcarbamate C14H11N5O2 详情 详情
(XXXII) 13114 1-[[(2S,3S)-2-(2,4-Difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole C12H11F2N3O 详情 详情
(XXXIV) 14909 1-isocyanato-4-nitrobenzene; 4-Nitrophenyl isocyanate 100-28-7 C7H4N2O3 详情 详情
(XXXIX) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(XL) 45578 (2R,3R)-2-(2,4-difluorophenyl)-3-[(2-hydroxyethyl)amino]-1-(1H-1,2,4-triazol-1-yl)-2-butanol C14H18F2N4O2 详情 详情
(XLI) 45579 N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-N-(2-hydroxyethyl)-N'-[4-(1H-1,2,3,4-tetraazol-1-yl)phenyl]urea C22H23F2N9O3 详情 详情
(XLII) 45580 N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-N-(2-hydroxyethyl)-N'-(4-nitrophenyl)urea C21H22F2N6O5 详情 详情
(XLIII) 45581 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-nitrophenyl)-2-imidazolidinone C21H20F2N6O4 详情 详情
Extended Information