• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】35452

【品名】2-phenyl-4-(trifluoromethyl)-1H-imidazole

【CA登记号】

【 分 子 式 】C10H7F3N2

【 分 子 量 】212.1742696

【元素组成】C 56.61% H 3.33% F 26.86% N 13.2%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(V)

The bromination of 1,1,1-trifluoroacetone (I) according to McBee and Burton gives 3,3-dibromo-1,1,1-trifluoroacetone (II), which is hydrolyzed with aqueous NaOAc to the glyoxal (III). The cyclization of (III) with benzaldehyde (IV) and ammonia in methanol yields 2-phenyl-4-(trifluoromethyl)-1H-imidazole (V), which is converted into the carbonitrile (VI) by reaction with hot aqueous ammonium hydroxide. The reduction of (VI) with diisobutylaluminum hydride in THF affords the carbaldehyde (VII), which is finally condensed with N-tert-butylhydroxylamine (VIII) by means of NaHCO3 in hot ethanol.

1 Dhainaut, A.; et al.; Synthesis, structure, and neuroprotective properties of novel imidazolyl nitrones. J Med Chem 2000, 43, 11, 2165.
2 Dhainaut, A.; Lestage, P.; Lockhart, B.; Tizot, A.; Goldstein, S. (ADIR et Cie.); Nitrone derivs., process for their preparation and pharmaceutical compsns. containing them. CA 2274621; EP 0967207; FR 2780404; JP 2000026428; US 6034250 .
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) 35449 1,1,1-trifluoroacetone 421-50-1 C3H3F3O 详情 详情
(II) 35450 3,3-dibromo-1,1,1-trifluoroacetone 431-67-4 C3HBr2F3O 详情 详情
(III) 35451 3,3,3-trifluoro-2-oxopropanal C3HF3O2 详情 详情
(IV) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(V) 35452 2-phenyl-4-(trifluoromethyl)-1H-imidazole C10H7F3N2 详情 详情
(VI) 35435 (1R)-2-[12-[(2R)-2-(benzoyloxy)propyl]-2,4,6,7,9,11-hexamethoxy-3,10-dioxo-3,10-dihydro-1-perylenyl]-1-methylethyl benzoate C46H42O12 详情 详情
(VII) 35454 2-phenyl-1H-imidazole-4-carbaldehyde C10H8N2O 详情 详情
(VIII) 35455 N-(tert-butyl)hydroxylamine; 2-(hydroxyamino)-2-methylpropane C4H11NO 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

The hydrolysis of 2-phenyl-4-(trifluoromethyl)-1H-imidazole (I) with 1N NaOH gives 2-phenyl-1H-imidazole-4-carboxylic acid (II), which is condensed with N,O-dimethylhydroxylamine (III) by means of TBTU and DIEA in dichloromethane to yield the amide (IV). The reduction of (IV) with DIBAL in THF affords 2-phenyl-1H-imidazole-4-carbaldehyde (V), which is finally condensed with N-tert-butylhydroxylamine (VI) by means of NaHCO3 in hot ethanol to provide the target nitrone.

1 Dhainaut, A.; et al.; Synthesis, structure, and neuroprotective properties of novel imidazolyl nitrones. J Med Chem 2000, 43, 11, 2165.
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) 35452 2-phenyl-4-(trifluoromethyl)-1H-imidazole C10H7F3N2 详情 详情
(II) 51473 2-phenyl-1H-imidazole-4-carboxylic acid C10H8N2O2 详情 详情
(III) 13361 (Methoxyamino)methane; N,O-Dimethylhydroxylamine 1117-97-1 C2H7NO 详情 详情
(IV) 51474 N-methoxy-N-methyl-2-phenyl-1H-imidazole-4-carboxamide C12H13N3O2 详情 详情
(V) 35454 2-phenyl-1H-imidazole-4-carbaldehyde C10H8N2O 详情 详情
(VI) 35455 N-(tert-butyl)hydroxylamine; 2-(hydroxyamino)-2-methylpropane C4H11NO 详情 详情
Extended Information