Sodium Hydroxide → 3-[4-(6-amino-pyridin-3-yl)-[1,2,3]triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide

Beteiligte Stoffe

Reaktionsschritte

To a stirring suspension of 310 mg (0.719 mmol) of 3-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide in 2 mL of EtOH and 2 mL of water was added dropwise 4M NaOH until the mixture became homogeneous. A solution of 142 mg (0.719 mmol) of sodium ascorbate in 0.5 mL of water was added, followed by 100 mg (0.719 mmol) 2-amino-4-ethynyl pyridine in 1 mL of EtOH. Finally 0.72 mL of 0.1 M CuSO4 was added, and the resulting mixture was stirred vigorously for 14 h. The mixture was then diluted with 40 mL of water and HOAc was added until a precipitate formed and the pH was about 6. The precipitate was filtered and washed with water and hexanes. The solids were chromatographed (0–5% MeOH/0.5% NH4OH in CH2Cl2) to provide 321 mg (0.584 mmol; 81%) of the title compound. ESI MS m/z 548 [C27H31N7O4S—H]−.

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