Pyridine → HCID 69585188, compound

Participants

Reaction Steps

To a cold solution (0° C.) of tetrahydro-2-furanmethanol (0.013 mL, 0.13 mmol) in toluene:methylene chloride (1:1, 0.03 mL) was added triphosgene (30 mg, 0.1 mmol) and quinoline (0.018 mL, 0.15 mmole) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was cooled at 0° C., diluted with 3 N HCl and extracted with ethyl acetate twice. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The cold (−40° C.) solution of crude chloroformate (0.075 mmol) in anhydrous tetrahydrofuran (0.5 mL) was added to amine from Example 8A (17 mg, 0.05 mmol) and pyridine (0.009 mL, 0.105 mmole) in anhydrous tetrahydrofuran (0.1 mL) at −40° C. The reaction mixture was allowed to warm at room temperature, stirred overnight and concentrated under reduced pressure. The residue was purified by reverse-phase HPLC to provide the titled compound.

Provenance & Evidence