Trifluoroacetic acid → 2-(4-methylpiperazine-1-carbonyl)-3-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile

Participants

Reaction Conditions

Reaction Steps

To a 35 ml vial, 2-(4-methylpiperazine-1-carbonyl)-3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile (0.100 g, 0.0001 mole) was taken in CH2Cl2 (8 ml) and cooled to 0° C. under N2 atm. TFA (2 ml, 0.0238 mole) was added drop wise at 0° C. and stirred for 16 h at room temperature. After completion of the reaction, the solvent was evaporated under reduced pressure from the reaction mixture and saturated NaHCO3 solution was added dropwise to make pH basic. The solid which precipitated out was filtered and washed with water and pentane. The solid (0.050 g) was taken in ethanol (20 ml), NaOAc.3H2O (0.226 g, 0.0016 mole) was added and the reaction mixture and stirred at room temperature for 32 hr. Ethanol was evaporated under reduced pressure from the reaction mixture and obtained solid material was washed with water and pentane. The crude compound was purified by triturating with pentane to yield 0.017 g of 2-(4-methylpiperazine-1-carbonyl)-3-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile.

Provenance & Evidence