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【结 构 式】

【分子编号】56733

【品名】2-(2-nitro-1H-imidazol-1-yl)acetic acid

【CA登记号】

【 分 子 式 】C5H5N3O4

【 分 子 量 】171.11252

【元素组成】C 35.1% H 2.95% N 24.56% O 37.4%

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:(IV)

The intermediate mixed anhydride (V) has been obtained as follows: the condensation of 2-nitroimidazole (I) with methyl 2-bromoacetate (II) by means of NaOMe in methanol gives 2-(2-nitro-1H-imidazol-1-yl)acetic acid methyl ester (III), which is hydrolyzed with NaOH to yield the corresponding acid (IV). Finally, this compound is condensed with isobutyl chloroformate by means of NMM in THF to afford the desired mixed anhydride intermediate (V). The condensation of 2,2,2-trifluoroacetaldehyde ethyl hemiacetal (VI) with nitromethane (VII) by means of K2CO3 gives 1,1,1-trifluoro-3-nitro-2-propanol (VIII), which is reduced with H2 over RaNi in ethanol to yield 3-amino-1,1,1-trifluoro-2-propanol (IX). Finally, this compound is condensed with the mixed anhydride intermediate (V) by means of NMM in THF to afford the target amide.

1 Tracy, M.; Kelson, A.B.; Workman, P.; Lewis, A.D.; Aboagye, E.O. (Cancer Research UK; SRI International); Fluorinated 2-nitroimidazole analogs for detecting hypoxic tumor cells. EP 0775117; JP 1998506104; US 5721265; WO 9604249 .
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) 10145 2-Nitro-1H-imidazole; 2-Nitroimidazole 527-73-1 C3H3N3O2 详情 详情
(II) 12309 methyl 2-bromoacetate; methyl bromoacetate 96-32-2 C3H5BrO2 详情 详情
(III) 10258 methyl 2-(2-nitro-1H-imidazol-1-yl)acetate; Methyl 2-nitro-1-imidazoleacetate 22813-31-6 C6H7N3O4 详情 详情
(IV) 56733 2-(2-nitro-1H-imidazol-1-yl)acetic acid C5H5N3O4 详情 详情
(V) 56734   C10H13N3O6 详情 详情
(VI) 26582 1-ethoxy-2,2,2-trifluoro-1-ethanol 433-27-2 C4H7F3O2 详情 详情
(VII) 39563 nitromethane 75-52-5 CH3NO2 详情 详情
(VIII) 56735 1,1,1-trifluoro-3-nitro-2-propanol C3H4F3NO3 详情 详情
(IX) 56736 3-amino-1,1,1-trifluoro-2-propanol 431-38-9 C3H6F3NO 详情 详情
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