Ammonia → HCID 59457842, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-fluoro-3-{6-[6-(4-fluorophenyl)-imidazo[2,1-b]oxazol-5-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl}-benzonitrile (0.15 g, 0.34 mmol; Example #K.1.19) in water (1 mL) and then was added NH4OH (28-30% in water, 2.0 mL, 51 mmol) and 1M NaOH (1 mL, 1.0 mmol). The reaction mixture was stirred at about 65° C. for about 8 h. Ammonia (0.5 M in 1,4-dioxane, 10 mL) was added and the reaction mixture was stirred about 72 h at about 65° C. The organic solvent was removed under reduced pressure and aqueous layer was buffered with ammonium acetate aqueous solution. The crude material was purified by reverse phase preparative chromatography (Table 1, Method e). The resulting material was purified by trituration with hot MeOH to afford the title compound (0.038 g, 23%) LC/MS (Table 1, Method a) Rt, =1.84 min; MS m/z: 458.1 (M+H)+.

Provenance & Evidence