Thiazolidinedione → HCID 89114984, compound

Participants

Reaction Conditions

Reaction Steps

An 8 mL round-bottomed vial was charged with tert-butyl((1-(6-formylpyrimidin-4-yl)piperidin-4-yl)methyl)carbamate (77.9 mg, 0.24 mmol, 1 equiv.), ethanol (1 mL), thiazolidine-2,4-dione (28.5 mg, 0.24 mmol, 1 equiv.) and triethylamine (68 μL, 0.48 mmol, 2 equiv.). Piperidine (1.04 mg, 23 μL of a solution of 52 μL in 0.95 mL ethanol, 0.012 mmol, 5% eq.) was added and Argon was bubbled through the solution. The reaction mixture was shaken at 85° C. for 18 h. LC-MS of the crude reaction mixture showed mostly the desired product. The solvent was evaporated. The residue was partitioned between EtOAc (10 mL) and 10% NH4Cl (5 mL). The organic layer was dried over Na2SO4. Evaporation of solvent gave the crude (Z)-tert-butyl((1-(6-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-4-yl)piperidin-4-yl)methyl)carbamate (79.8 mg, 78%). LC-MS: M+1=420.

Provenance & Evidence