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【结 构 式】

【分子编号】43499

【品名】4-(2,2,3,3-tetrafluoropropoxy)phenylamine; 4-(2,2,3,3-tetrafluoropropoxy)aniline

【CA登记号】

【 分 子 式 】C9H9F4NO

【 分 子 量 】223.1702128

【元素组成】C 48.44% H 4.06% F 34.05% N 6.28% O 7.17%

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)

Treatment of 4-nitrophenol (I) with propyl iodide derivative (II) and K2CO3 in DMF, followed by reduction with hydrazine hydrate, FeCl3 and activated carbon affords (III). Conversion of aniline derivative (III) into phenylcarbamate (IV) by means of PhOCOCl and treatment of (IV) with hydrazine hydrate yields semicarbazide (V), which is then subjected to cyclization with formamidine (VI) to give triazolone derivative (VII). Benzyl (S)-lactate (VIII) is converted to triflate (IX) by means of Tf2O in the presence of DIEA and its reaction with triazolone (VII) and NaH in DMF provides derivative (X). Debenzylation of (X) by hydrogenolysis over Pd/C followed by treatment with oxalyl chloride in CH2Cl2/DMF furnishes chloride (XI), which reacts with 1,3-difluorobenzene (XII) in CH2Cl2 in the presence of AlCl3 to yield intermediate (XIII).

1 Tamura, N.; Okonogi, K.; Hayashi, R.; Matsushita, Y.; Kitazaki, T.; Tasaka, A.; Itoh, K.; Optically active antifungal azoles.VI. Synthesis and antifungal activity of N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-N'-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones. Chem Pharm Bull 1996, 44, 2, 314.
2 Kitazaki, T.; et al.; Optically active antifungal azoles. IX. An alternative synthetic route for 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone and its analogs. Chem Pharm Bull 1999, 47, 3, 360.
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) 11236 4-Nitrophenol; p-Nitrophenol 100-02-7 C6H5NO3 详情 详情
(II) 43498 1,1,2,2-tetrafluoro-1-iodopropane C3H3F4I 详情 详情
(III) 43499 4-(2,2,3,3-tetrafluoropropoxy)phenylamine; 4-(2,2,3,3-tetrafluoropropoxy)aniline C9H9F4NO 详情 详情
(IV) 43500 phenyl 4-(2,2,3,3-tetrafluoropropoxy)phenylcarbamate C16H13F4NO3 详情 详情
(V) 43501 N-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-1-hydrazinecarboxamide C10H11F4N3O2 详情 详情
(VI) 15369 Iminoformamide; Methanimidamide 463-52-5 CH4N2 详情 详情
(VII) 43502 4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one C11H9F4N3O2 详情 详情
(VIII) 43503 benzyl (2S)-2-hydroxypropanoate 56777-24-3 C10H12O3 详情 详情
(IX) 43504 benzyl (2S)-2-[[(trifluoromethyl)sulfonyl]oxy]propanoate C11H11F3O5S 详情 详情
(X) 43505 benzyl (2R)-2-[5-oxo-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoate C21H19F4N3O4 详情 详情
(XI) 43506 (2R)-2-[5-oxo-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoyl chloride C14H12ClF4N3O3 详情 详情
(XII) 13095 m-Difluorobenzene; 1,3-Difluorobenzene 372-18-9 C6H4F2 详情 详情
(XIII) 43507 2-[(1R)-2-(2,4-difluorophenyl)-1-methyl-2-oxoethyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one C20H15F6N3O3 详情 详情
Extended Information