Trifluoroacetic acid → HCID 68051772, compound

Participants

Reaction Steps

A solution of ((R)-benzyl 4-(4-(6-(3-(tert-butoxycarbonylamino)piperidin-1-yl)-3-carbamoylpyridin-2-ylamino)phenyl)piperazine-1-carboxylate) (4.71 g, 7.5 mmol) in CH2Cl2 (5 ml) was treated with 5 mL of TFA and stirred at rt for 5 h. The reaction mixture was concentrated and the residue was partitioned between 1N NaOH and CH2Cl2. The aqueous phase was extracted with CH2Cl2 and the combined organic layers were concentrated. The brown residue was purified by MPLC (ISCO, 8% NH4OH/MeOH/CH2Cl2, 120 g silica gel column) and the fractions containing product were combined and concentrated. The resulting solid was triturated with CH2Cl2 to obtain 1.9 g of (R)-benzyl 4-(4-(6-(3-aminopiperidin-1-yl)-3-carbamoylpyridin-2-ylamino) phenyl)piperazine-1-carboxylate as a white solid. A second trituration gave an additional 320 mg of product as a light yellow solid.

Provenance & Evidence