Ammonium formate → HCID 58865722, compound

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Reaction Steps

N-(3,5-dichloro-2,6-bis-((3R,5S)-3,5-bis-(tert-butoxycarbonylamino)-piperidin-1-yl)-pyridin-4-yl)-benzene-1,4-diamine (140) (0.205 g, 0.233 mmol) was dissolved in MeOH (15 mL). Pd/C (1 g, 10%, wet) was added followed by ammonium-formate (2 g). The mixture was shaken in a Teflon septum capped 40 mL I-Chem vial, with occasional venting, for 3 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 using a gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane in 30 minutes followed by 100% EtOAc in 10 minutes) to give the desired product (141) as a yellow/green oil (0.08 g, 0.098 mmol, 42.3% yield). LC-MS (ESI): (exact mass: 811.50) m/e=812.7 [M+1]+ (100%).

Provenance & Evidence