Trifluoroacetic acid → N-tert-butyl-2-(4-(2-cyano-3-(dimethylamino)-3-oxoprop-1-enyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Steps

In a 25 ml one necked round bottom flask, N-tert-butyl-2-(4-(2-cyano-3-(dimethylamino)-3-oxoprop-1-enyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.1 g, 0.00019 mol) was taken in CH2Cl2 (10 ml) followed by dropwise addition of TFA (2.0 ml) at 0°-5° C. and the reaction was allowed to stir at room temperature for 24 hr. After completion of the reaction, the pH of the solution was adjusted to neutral by the addition of saturated sodium bicarbonate solution and extracted with CH2Cl2 and the combined organic layer was dried over anhy. sodium sulphate and concentrated to obtain crude mixture which was dissolved in ethanol (10 ml). NaOAc.3H2O (0.242 g, 0.00178) was added and the reaction mixture was stirred at room temperature for 20 hr. Ethanol was distilled out and the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate, concentrated to afford crude product which was purified using column purification by eluting the compound with 50% ethyl acetate in hexanes to yield 14.0 mg of N-tert-butyl-2-(4-(2-cyano-3-(dimethylamino)-3-oxoprop-1-enyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide.

Provenance & Evidence