Pyridine → HCID 86594306, compound

Participants

Reaction Steps

To 68A (96.0 mg, 0.269 mmol) in MeOH (2.7 mL) and water (5 drops) was added pyridine (109 μL) and hydroxylamine hydrochloride (93.0 mg, 1.34 mmol) and the whole was stirred overnight at rt. The reaction was concentrated then diluted with ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated. The resulting residue was purified via preparative HPLC (YMC ODS C-18, 30×100 mm, eluting with 60-100% solvent B (A=90% H2O-10% MeOH and B=10% H2O-90% MeOH) over 10 min; Flow rate at 40 mL/min; UV detection at 220 nm) to provide a solid which was re-purified via preparative HPLC (YMC ODS C-18, 30×100 mm, eluting with 40-70% solvent B (A=90% H2O-10% CH3CN and B=10% H2O-90% CH3CN) over 12 min; Flow rate at 40 mL/min; UV detection at 220 nm) to provide the title compound (48.0 mg) as a white solid. MS: m/z 371 [M−H]−.

Provenance & Evidence