Ethylenediamine → 2-(5-(5-(aminomethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide

Participants

Reaction Steps

To 2-(5-(5-(aminomethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide 10-1b (211 mg, 0.364 mmol) dissolved in dichlormethane (2.0 ml) was added TFA (2.0 ml, 26.0 mmol). The reaction stirred at room temp for 1.5 hrs, concentrated and the residue dissolved in MeOH (2.0 ml). NaOH (0.255 ml, 2.55 mmol) and ethylenediamine (0.049 ml, 0.728 mmol) were added and the reaction stirred for 2 hrs at room temperature. The reaction was then acidified with trifluoroacetic acid, filtered and purified by RP-HPLC (water:acetonitrile w/0.1% TFA, C-18, 15-50%). The pure fractions concentrated to remove acetonitrile and mixture neutralized with saturated sodium bicarbonate. The product was extracted with ethyl acetate (3×10 mL). The combined organics were then washed with brine, dried with sodium sulfate, filtered and concentrated to afford the product 10-1c (140 mg, 89%).

Provenance & Evidence