Ammonia → 4-(1-amino-ethyl)-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A 4 mL vial was charged with 4-acetyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-benzenesulfonamide (synthesized according to general procedures F and G, 100 mg, 0.23 mmol), 7 M NH3 in MeOH (100 μL, 0.70 mmol), and 2 mL THF. The resulting slurry was stirred well, then titanium ethoxide (98 μL, 47 mmol) was added and the mixture heated to 60° C. for three hours. Sodium cyanoborohydride (22 mg, 0.35 mmol) and acetic acid (5 drops) were then added and the mixture was maintained at 60° C. overnight. The reaction mixture was diluted with ˜2 mL of acetonitrile/H2O and purified by reversed phase HPLC to afford 4-(1-amino-ethyl)-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-benzenesulfonamide: MS (ES) M+H expected 428.0, found 428.0.

Provenance & Evidence