反应详情

1,4-Dioxane (5 mL), 2-chloro-N-[1-(2-hydrazino-2-oxoethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 15; 300 mg, 0.72 mmol), cyanogen bromide (80 mg, 0.75 mmol) and 1,4-dioxane (2 mL) were added to a solution of Na2CO3 (77 mg, 0.72 mmol) in H2O (1.7 mL) and stirred for 18 hours. The mixture was diluted with EtOAc (50 mL) and THF (20 mL) and washed with H2O (25 mL). The organic was dried (Na2SO4), filtered and evaporated. The residue was purified by reverse phase column chromatography to give a brown solid. This was triturated with refluxing Et2O (25 mL), filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford the title compound (63 mg, 20%) as a brown powder.

1. washwashed with H2O (25 mL)
2. dry with materialThe organic was dried (Na2SO4)
3. filtrationfiltered
4. customevaporated
5. customThe residue was purified by reverse phase column chromatography
6. customto give a brown solid
7. customThis was triturated with refluxing Et2O (25 mL)
8. filtrationfiltered
9. washwashed with Et2O (25 mL)