Ethyl Acetate → HCID 67443227, compound

Participants

Reaction Steps

To a solution of 113 (168 mg, 0.332 mmol) in DMF (8 mL) at RT was added DIPEA (0.203 mL, 1.161 mmol), followed by HATU reagent (378 mg, 0.995 mmol). The reaction mixture was stirred overnight at RT. Ethyl acetate was added, the reaction mixture was washed with water, saturated ammonium chloride solution and saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated. The residue was purified via Biotage (0-50% MeOH/EtOAc; SNAP 50 g cartridge) to give an off-white solid which upon trituration with ether/acetone afforded title compound 115-A (20 mg, 11% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): contains 2 rotamers: 8.74 (s, 1H), 8.54 (d, 1H, J=5.5 Hz), 8.10, 8.07 (2s, 1H), 7.94, 7.89 (2d, 2H, J=8.2 Hz), 7.78 (dd, 1H, J1=2.4 Hz, J2=13.5 Hz), 7.44-7.38 (m, 3H), 7.25-7.22 (m, 1H), 6.63-6.61 (m, 2H), 4.73-4.61 (m, 3H), 4.28, 4.14 (2d, 2H, J=5.5 Hz), 3.51-3.40 (m, 4H), 3.27 (s, 3H), 2.60-2.56 (m, 1H), 0.71-0.67 (m, 2H), 0.48-0.44 (m, 2H). MS: 565.5 (MH+).

Provenance & Evidence