Water → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((S)-2-azido-1-phenyl-ethyl)-amide

Participants

Reaction Steps

To a solution of 3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)thiophene-2-carboxylic acid (130.00 mg; 0.50 mmol; 1.00 eq.), (1S)-2-azido-1-phenylethanamine (129.67 mg; 0.55 mmol; 1.10 eq.), n,n-diisopropylethylamine (0.33 ml; 2.01 mmol; 4.00 eq.) in DMF (2.00 ml), O-(7-azabenzotriazol-1-yl)-n,n,n′,n′-tetramethyluronium hexafluoro-phosphate (209.70 mg; 0.55 mmol; 1.10 eq.) was added. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water. The solid was too tiny to be filtered. The aqueous mixture was extracted with ethyl acetate to afford the title compound in 79% yield. LCMS: m/e 404 (M+H). 1H NMR (DMSO-d6): ppm 11.56 (1H, br, s.), 10.25 (1H, s.), 8.72 (1H, d, J=8.44 Hz), 8.02 (1H, d, J=5.48 Hz), 7.85 (1H, d, J=5.52 Hz), 7.50 (1H, d, J=5.48 Hz), 7.42-7.44 (1H, m), 7.26-7.35 (4H, m), 6.81 (1H, d, J=5.16 Hz), 6.40 (1H, dd, J=3.28, 1.84 Hz), 5.27-5.32 (1H, m), 3.79 (1H, dd, J=12.84, 9.52 Hz), 3.60 (1H, dd, J=12.48, 4.76 Hz).

Provenance & Evidence