Acetyl chloride → HCID 72721200, compound

Participants

Reaction Steps

Acetyl chloride (24 μL, 0.34 mmol) and triethylamine (47 μL, 0.34 mmol) were added to a solution of Example 78 (154 mg, 0.34 mmol) in DCM (3 mL). The reaction mixture was stirred at room temperature for 2.5 h. Further acetyl chloride (12 μL, 0.17 mmol) and triethylamine (23 μL, 0.17 mmol) were added, and the mixture was stirred at room temperature for 24 h. Further acetyl chloride (49 μL, 0.68 mmol) and triethylamine (94 μL, 0.34 mmol) were added, and the mixture was stirred for 3 days. The solvent was removed and the mixture was purified by silica gel chromatography, eluting with a 0-5% gradient of 7M ammonia/methanol in DCM, to afford the title compound (24.8 mg, 14%) as a white solid. δH (250 MHz, CDCl3) 8.09 (d, J 8.4 Hz, 2H), 7.64 (d, J 19.1 Hz, 2H), 7.42 (s, 1H), 7.35 (d, J 8.3 Hz, 2H), 7.26 (m, 1H), 7.07 (td, J 8.4, 2.1 Hz, 2H), 6.94-6.24 (m, 2H), 4.24 (s, 2H), 2.49 (s, 3H), 2.25 (s, 3H), 2.09 (s, 3H). Method A HPLC-MS: MH+ m/z 500, RT 1.96 minutes (100%).

Provenance & Evidence