Hydrazine → HCID 58865789, compound

Participants

Reaction Conditions

Reaction Steps

N-[4-(3,5-dichloro-2,6-bis-((3R,5S)-3,5-bis-(tert-butoxycarbonylamino)-piperidin-1-yl)-pyridin-4-ylamino)-phenyl]-acetamide (139) (0.849 g, 0.92 mmol) was dissolved in MeOH (5 mL) and NMP (10 mL). Hydrazine (10 mL) was added and the mixture was heated at 80° C. with shaking in a 40 mL I-Chem vial for 5 days. LC-MS at this point indicated nearly complete deprotection. The mixture was diluted with EtOAc (50 mL), washed with water (4×25 mL) and brine (25 mL) via extraction, dried over MgSO4 and concentrated to give a yellow oil. Purification by flash chromatography using a gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane in 30 minutes) gave the desired product (140) as a beige powder upon concentration (0.728 g, 0.826 mmol, 89.8% yield). LC-MS (ESI): (exact mass: 879.42) m/e=880.5 [M+1]+ (100%).

Provenance & Evidence