Thiazolidinedione → 5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

To a 35 ml reaction vial 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl amino)benzaldehyde (0.200 g, 0.0004 mole) and thiazolidine-2,4-dione (0.155 g, 0.0105 mole) were taken in ethanol (10 ml). Piperidine acetate (3.3M solution in water) (3 ml) was added at RT. The reaction mixture was heated to 80° C. for 16 hrs. After completion of the reaction, ethanol was evaporated under reduced pressure and diluted with EtOAc. Organic layer was washed with water, dried over Na2SO4 and evaporated to get crude product which was purified using column purification by eluting the compound with 10-20% EtOAc in Hexanes to yield 0.170 g of 5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione.

Provenance & Evidence