Hydrazine → 3-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-2,2-dimethylpropanoic acid

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round-bottom flask 6-(4-fluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole (0.20 g, 0.65 mmol; prepared using A from 6-(4-fluorophenyl)-imidazo[2,1-b]oxazole [prepared according to WO2004110990A2, Example 1, Steps 1-3] with NIS, C using 2-fluoropyridine-5-boronic acid [Asymchem], D using hydrazine) and 3,3-dimethyldihydrofuran-2,5-dione (0.091 g, 0.71 mmol) were dissolved in 1,4-dioxane (5 mL) and the mixture was heated to about 100° C. After about 2 h the reaction was cooled to ambient temperature and concentrated in vacuo. The crude material was dissolved in DCM and crystallized upon the addition of Et2O. The resulting solid was filtered and dried under vacuum to provide the title compound as a white solid (0.22 g, 81%): LC/MS (Table 1, Method a) Rt, =1.86 min; MS m/z: 420.2 (M+H)+.

Provenance & Evidence