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

Participants

Reaction Steps

To a 50 ml three necked round bottom flask, 4-(7-pivaloyl-5-((2-(trimethylsilyl)-ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-2-ylamino)benzaldehyde (0.104 g, 0.00023 mole) and 3-ethylthiazolidine-2,4-dione (0.067 g, 0.00046 mole) was taken in ethanol (3 ml). Piperidine acetate (3.3 M solution in water) (0.1 ml) was added dropwise at RT. The reaction mixture was refluxed for 6 hrs. After completion of the reaction, ethanol was distilled out and water was added to residue. Aq. layer was extracted with ethyl acetate, the combined organic layers were dried over Na2SO4, filtered and concentrated to afford crude product which was purified by triturated with n-pentane. The solid was filtered and dried under vacuum to yield 0.070 g of 3-ethyl-5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione which was converted to the title compounds as described in Example 6 above.

Provenance & Evidence