1,1'-Thiocarbonyldi-2(1H)-pyridone → 2-(4-(4-(2-(5-Cyclobutyl-1,3,4-thiadiazol-2-ylamino)pyrimidin-5-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a reaction vial containing methyl 2-(4-(4-(2-aminopyrimidin-5-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (40 mg, 0.11 mmol) was added dichloromethane (1 ml) at room temperature. 1,1′-thiocarbonyldipyridin-2(1H)-one (29 mg, 0.12 mmol) was added and the resulting mixture was heated to 50° C. for overnight. The mixture was cool down to room temperature and cyclobutanecarbohydrazide (19 mg, 0.17 mmol) was then added and stirred at room temperature for another hour. The content was then concentrated to dryness and the resulting residue was taken up in MeOH to form a nice slurry. The slurry was filtered and washed with small amount of MeOH to afford the title compound as off-white solid after drying (48 mg, 83% yield). LC/MS, ESI-MS(+): 510.4, RT: 1.26 (Condition E)

Provenance & Evidence