Ammonium formate → HCID 58865616, compound

Participants

Reaction Steps

4,6-Bis-((3R,5S)-3,5-bis-(tert-butoxycarbonylamino)-piperidin-1-yl)-3,5-dichloro-2-(4-aminophenyl-amino)-pyridine (167) (0.127 g, 0.144 mmol) was dissolved in MeOH (15 mL). Pd/C (0.33 g, 10%, wet) was added followed by ammonium-formate (0.66 g). The mixture was shaken in a Teflon septum capped 40 mL I-Chem vial, with occasional venting, for 16 hours. LC-MS indicated complete de-chlorination at this point. The mixture was filtered through a plug of Celite and the filtrate was concentrated and purified by flash chromatography on silica gel (eluting with 15–100% EtOAc in hexane for 30 minutes followed by 100% EtOAc for 10 minutes) to give the desired product (168) as an off-white powder (0.055 g, 0.0677 mmol, 47% yield). LC-MS (ESI): (exact mass: 811.5) m/e=812.6 [M+1]+.

Provenance & Evidence