Реакция #71499

Уравнение реакции

Sodium triacetoxyborohydride

8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (4-formyl-1H-imidazol-2-yl)-amide

trifluoroethylamine

→

title compound

Выход 62.3%

8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid {4-[(2,2,2-trifluoro-ethylamino)-methyl]-1H-imidazol-2-yl}-amide

Выход 62.3%

Растворители

DCM

Условия реакции

Обработка

1. 1
   Другоеquenched by addition of H2O
2. 2
   Экстракцияextracted with DCM
3. 3
   ПромывкаThe organic phase was washed with a saturated aqueous solution of NaHCO3
4. 4
   Сушкаdried (Na2SO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 98:1:1)

Методика

Sodium triacetoxyborohydride (101 mg, 0.476 mmol, 3 equiv) was added to a suspension of 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (4-formyl-1H-imidazol-2-yl)-amide (75 mg, 0.159 mmol) and trifluoroethylamine (15 μl, 0.188 mmol), 1.18 equiv) in DCM (3 mL) at rt, under an argon atmosphere. The reaction mixture was stirred for 18 h at rt, quenched by addition of H2O and extracted with DCM. The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 98:1:1) followed by trituration in Et2O to afford 55 mg of the title compound as a yellow solid: ES-MS: 555 [M+H]+; tR=3.78 min (System 1); TLC: Rf=0.55 (DCM/MeOH, 9:1).

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