Ethylenediamine → N2-(5-{5-[(methylsulfonyl)amino]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridin-3-yl)-N-(2,2,2-trifluoroethyl)valinamide

Participants

Reaction Steps

To a solution of N2-[5-(5-[(methylsulfonyl)amino]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]-N-(2,2,2-trifluoroethyl)valinamide 5-3a (57 mg, 0.093 mmol) from step 1 in DCM (2 mL) was added TFA (0.714 mL, 9.27 mmol) and the resultant mixture was stirred for 2 h. The mixture was concentrated in vacuo, resuspended in MeOH (1 mL) and to this was added ethylenediamine (0.013 mL, 0.185 mmol) and sodium hydroxide (10 M aq) (0.065 mL, 0.649 mmol). After 18 h, the reaction was transferred to vial with an additional 1 mL of dimethylsulfoxide and this solution was purified by mass triggered reverse phase HLPC. The fractions containing product 5-3 were basified with NaHCO3, dried over MgSO4, filtered and concentrated.

Provenance & Evidence