Trifluoroacetic acid → 5-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

In a 35 ml vial, 5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione (0.100 g, 0.0001 mole) was taken in 8 ml CH2Cl2 and cooled to 0° C. under N2 atm. TFA (2 ml, 0.0268 mole) was added dropwise at 0° C. and the reaction mixture was stirred for 16 h at room temperature. After completion of the reaction, solvent was evaporated under reduced pressure from the reaction mixture and saturated NaHCO3 solution was added dropwise to make Ph basic. The solid that precipitated out was washed with water and pentane and 0.050 g of the solid was taken up in ethanol (20 ml) and NaOAc.3H2O (0.246 g, 0.0018 mole) was added. The reaction mixture was stirred at room temperature for 16 hr. Ethanol was evaporated under reduced pressure and the solid was washed with water and pentane. The crude compound was purified by triturating with pentane to yield 0.018 g of the title compound.

Provenance & Evidence