Pyridine → HCID 59049327, compound

Participants

Reaction Steps

To a solution of (2S)-N-[3-(3-Pyridyl)-1-propyl]-1-(benzyloxycarbonyl)azetidine-2-carboxamide from Reference Example 16 (295.7 mg, 0.837 mmol, 1.0 eq) in dry 1,2-dichloroethane (8.5 mL) was added pyridine (100 μL, 1.24 mmol, 1.5 eq) under argon. Phosphorus pentachloride (263 mg, 1.26 mmol, 1.5 eq) was added in one portion and the mixture was stirred at about room temperature for about 4 hours. A dry HN3 solution (prepared by mixing 6.5 g of NaN3 in 25 mL of water with 8.3 mL conc. HCl, extracting with 25 mL 1,2-dichloroethane, drying over magnesium sulfate and filtering) was added and the reaction mixture was stirred at about room temperature overnight. The organic phase was washed with concentrated NH4OH solution (2×5 mL), dried and the solvents removed under vacuum. Flash chromatography (5-10% methanol in dichloromethane) gave 125.3 mg (40% yield) of the product as a colorless oil. 1H NMR (CDCl3) δ 2.11-3.51 (series of m, 7H); 4.08-5.40 (series of m, 6H); 7.12-7.57 (m, 7H); 8.37-8.51 (m, 2H).

Provenance & Evidence