5-Nitro-2-Furoic Acid → 1-(9H-carbazol-4-yloxy)-3-{[1-(5-nitro-2-furoyl)piperidin-4-yl]amino}propan-2-ol

Participants

Reaction Steps

To a solution of 5-Nitrofuroic acid (0.14 g, 0.88 mmol) in DMF (6 mL) was added TEA (0.17 mL, 1.2 mmol), EDCI (0.2 g, 1.0 mmol), HOBt (0.031 g, 0.23 mmol), followed by 1-(9H-carbazol-4-yloxy)-3-(piperidin-4-ylamino)propan-2-ol (0.2 g, 0.6 mmol, prepared by following the procedure described in step 11, example 64). The reaction was stirred at room temperature for 12 hours and was diluted with DCM (25 mL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4, concentrated and purified by silica gel column chromatography using DCM/MeOH (9.5:0.5) to afford the title compound as red colored paste (45 mg, 32% yield). 1H NMR (400 MHz, DMSO): δ 1.20-1.80 (m, 3H), 1.90-2.30 (m, 2H), 2.50-3.60 (m, 6H), 4.00-4.60 (m, 3H), 6.72 (d, 1H, J=8.0 Hz), 6.90-7.60 (m, 6H), 7.77 (d, 1H, J=3.6 Hz), 8.22 (d, 1H, J=8.0 Hz), and 11.30 (s, 1H). MS m/z: 478.1 (M+).

Provenance & Evidence