Diisopropylethylamine → HCID 67542725, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 28 (2 973 mg; 11.60 mmol) and DIEA (3.94 mL; 23.2 mmol) in anhydrous DMF (10 mL) at 0° C. was added HATU (4 410 mg; 11.60 mmol). The reaction mixture was stirred at 0° C. for 10 min. Intermediate 68 (2 300 mg; 11.05 mmol) was added at once. The reaction mixture was stirred at 0° C. for 15 min and RT for 2 h. EtOAc was added and the organic layer was washed with water and brine (50 mL), dried (MgSO4) and the solvents were removed under reduced pressure to give an oil. The oil was taken up with toluene (70 mL) and pyridine (10 mL). The resulting mixture was heated at 110° C. overnight. EtOAc was added and the organic layer was washed with water and brine (50 mL), dried (MgSO4) and the solvents were removed under reduced pressure to give a yellow oil. The crude material was purified by flash chromatography (EtOAc/cHex) to afford the title compound as an oil. 1H NMR: (DMSO-d6, 300 MHz) δ 8.33 (m, 1H), 8.17 (m, 3H), 7.76 (m, 2H), 7.43 (d, J=7.9 Hz, 1H), 7.38-7.25 (m, 3H), 7.16 (m, 1H), 5.90 (s, 1H), 4.23 (d, J=12.9 Hz, 1H), 4.17 (d, J=12.9 Hz, 1H), 4.15-3.98 (m, 4H), 3.25 (s, 3H), 2.31 (t, J=7.40 Hz, 2H), 2.04 (s, 3H). LC/MS (Method B): 429.2 (M+H)+ no (M−H)−. HPLC (Method A) Rt: 5.53 min (purity: 89.8%).

Provenance & Evidence