Reaction Steps
A 50 mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 102c (100 mg, 0.16 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (HATU, 152 mg, 0.40 mmol), triethylamine (TEA, 8 drops), THF (10 mL), and 2-aminoacetonitrile (5 drops). The mixture was heated at 30° C. for 5 h. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 102 (30 mg, 28%) as a white solid. MS: [M+H]+ 663.2. 1H NMR (500 MHz, DMSO-d6) δ 8.88 (d, J=6.0 Hz, 1H), 8.81 (s, 1H), 8.74 (s, 1H), 8.47 (d, J=5.0 Hz, 1H), 7.95 (d, J=5.5 Hz, 1H), 7.71 (s, 1H), 7.35 (d, J=4.5 Hz, 1H), 6.58-6.55 (m, 2H), 5.02 (s, 1H), 4.53-4.51 (m, 1H), 4.43-4.40 (m, 1H), 4.23-4.15 (m, overlap, 5H), 3.86-3.84 (m, 1H), 3.72-3.69 (m, 1H), 3.62 (s, 3H), 3.60-3.56 (m, 1H), 3.51-3.43 (m, 2H), 3.10-3.08 (m, 1H), 2.62-2.54 (m, 2H), 2.43 (s, 2H), 2.18-2.16 (m, 1H), 2.06-2.04 (m, 1H), 1.22 (s, 6H).
