Dimethylformamide → HCID 53475696, compound

Participants

Reaction Conditions

Reaction Steps

Commercially available p-fluorobenzylamine (0.76 ml, 6.7 mmol) was dissolved in 40 ml of AcOEt and at 0° C. triphosgene (1.98 g, 1 equiv.) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (900 mg, 6 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1×30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 420 mg of a white solid. Yield=23% 1HNMR (DMSO, 200 MHz) δ 4.29 (2H, d, J=6 Hz), 6.62 (1H, dd, J=7.6 Hz, J′=1.2 Hz), 6.80 (2H, m), 6.95 (1H, dd, J=8.2 Hz, J′=1.2 Hz), 7.15 (2H, m), 7.35 (2H, m), 8.23 (1H, bs), 9.96 (1H, bs), 10.59 (1H, bs); [M+1] 301.1 (C15H13FN4O2 requires 300.29).

Provenance & Evidence