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【结 构 式】

【分子编号】45558

【品名】N,N-dibenzyl-N-(4-nitrophenyl)amine; N,N-dibenzyl-4-nitroaniline

【CA登记号】

【 分 子 式 】C20H18N2O2

【 分 子 量 】318.3752

【元素组成】C 75.45% H 5.7% N 8.8% O 10.05%

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:(VII)

The condensation between 4-fluoronitrobenzene (I) and tetrazole (II) provided a mixture of regioisomeric (4-nitrophenyl)tetrazoles (III) and (IV). Reduction of this mixture employing hydrazine and FeCl3 gave the corresponding mixture of amino derivatives from which the required isomer (V) was isolated by column chromatography. Alternatively, 4-nitroaniline (VI) was converted into the desired (4-nitrophenyl)tetrazole regioisomer (III) by reaction with sodium azide and trimethyl orthoformate in HOAc. Subsequent reduction of the nitro group of (III) employing hydrazine and FeCl3 gave aniline (V). This compound was also obtained by another alternative procedure consisting in protection of 4-nitroaniline (VI) as the N,N-dibenzyl amine (VII), followed by reduction of the nitro group and cyclization with NaN3 and trimethyl orthoformate to afford tetrazole (VIII). Further hydrogenolysis of the benzyl protecting groups of (VIII) yielded 1-(4-aminophenyl)tetrazole (V). Aniline (V) was then converted to the intermediate phenyl carbamate (IX) by treatment with phenyl chloroformate in pyridine. Optionally, the intermediate phenyl carbamate (IX) was converted into the aryl imidazolone (XII) by condensation with 2,2-diethoxyethylamine (X) and then acid-catalyzed cyclization of the resulting N-(2,2-diethoxyethyl)urea (XI) to give (XII).

4 Itoh, K.; Okonogi, K.; Tasaka, A. (Takeda Chemical Industries, Ltd.); Azole cpds., their production and use. EP 0809640; JP 1997183769; WO 9625410 .
5 Kitazaki, T.; Matsushita, Y.; Hosono, H.; Itoh, K.; Mitsudera, H. (Takeda Chemical Industries, Ltd.); Triazole derivs. and their production. EP 0884311 .
1 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.
2 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.
3 Hosono, H.; Itoh, K.; Kitazaki, T.; Ichikawa, T.; Okonogi, K.; Tasaka, A.; Matsushita, Y.; Hayashi, R.; Optically active antifungal azoles. X. Synthesis and antifungal activity of N-[4-(azolyl)phenyl] and N-[4-(azolylmethyl)phenyl]-N'[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H,1,2,4-triazol-1-yl)propyl]-azolones. Chem Pharm Bull 2000, 48, 12, 1935.
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) 14153 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene 350-46-9 C6H4FNO2 详情 详情
(II) 32408 1H-1,2,3,4-tetraazole; Tetrazole 288-94-8 CH2N4 详情 详情
(III) 45555 1-(4-nitrophenyl)-1H-1,2,3,4-tetraazole C7H5N5O2 详情 详情
(IV) 45556 2-(4-nitrophenyl)-2H-1,2,3,4-tetraazole 67-97-0 C7H5N5O2 详情 详情
(V) 45557 4-(1H-1,2,3,4-tetraazol-1-yl)phenylamine; 4-(1H-1,2,3,4-tetraazol-1-yl)aniline C7H7N5 详情 详情
(VI) 15547 4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline 100-01-6 C6H6N2O2 详情 详情
(VII) 45558 N,N-dibenzyl-N-(4-nitrophenyl)amine; N,N-dibenzyl-4-nitroaniline C20H18N2O2 详情 详情
(VIII) 45559 N,N-dibenzyl-N-[4-(1H-1,2,3,4-tetraazol-1-yl)phenyl]amine; N,N-dibenzyl-4-(1H-1,2,3,4-tetraazol-1-yl)aniline C21H19N5 详情 详情
(IX) 45560 phenyl 4-(1H-1,2,3,4-tetraazol-1-yl)phenylcarbamate C14H11N5O2 详情 详情
(X) 10331 2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal 645-36-3 C6H15NO2 详情 详情
(XI) 45561 N-(2,2-diethoxyethyl)-N'-[4-(1H-1,2,3,4-tetraazol-1-yl)phenyl]urea C14H20N6O3 详情 详情
(XII) 45562 1-[4-(1H-1,2,3,4-tetraazol-1-yl)phenyl]-1,3-dihydro-2H-imidazol-2-one C10H8N6O 详情 详情
Extended Information