Triethylamine → tert-butyl 4-(4-fluoro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate

Participants

Reaction Steps

2-(1-(tert-Butoxycarbonyl)piperidin-4-ylamino)-6-fluorobenzoic acid (1.081 g, 3.19 mmol) and triethylamine (0.534 ml, 3.83 mmol) were combined and suspended in toluene (20 mL). Diphenyl azidophosphate (0.826 ml, 3.83 mmol) was added to the mixture. Reaction stirred at room temperature for 35 minutes. The reaction was heated to 80° C. for 1 hour. Solvent was removed in vacuo. Silica gel chromatography eluting ethyl acetate-hexanes afforded the title compound as white solid in 97% yield. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 9.64 (s, 1 H) 6.94-7.02 (m, 1 H) 6.91 (d, J=8.24 Hz, 1 H) 6.82 (t, J=9.15 Hz, 1 H) 4.42-4.54 (m, 1 H) 4.31 (d, J=10.07 Hz, 2 H) 2.86 (t, J=12.67 Hz, 2 H) 2.21-2.35 (m, 2 H) 1.78-1.87 (m, 2 H) 1.49 (s, 9 H).

Provenance & Evidence