Hydrochloric Acid → Benzamide

Participants

Reaction Steps

To Int-3 (146 mg, 0.43 mmol) in NMP (6 mL) were added HATU (247 mg, 0.65 mmol), O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine (76 mg, 0.65 mmol) and NMM (0.15 mL, 1.3 mmol) and stirred. After 2 hours, additional O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine (51 mg, 0.43 mmol), HATU (82 mg, 0.22 mmol) and NMM (0.1 mL) were added and stirred at room temperature for 1 hour. Then methanol (10 mL) and 1N HCl (12 mL) was added to the reaction mixture and stirred at room temperature for 1 hour. The reaction mixture was then diluted with water and acetonitrile and directly purified by preparative HPLC affording Compound 5 as tan solid, after lyophilization. MS found for C18H20N67O2 as (M+H)+ 353.2. 1H NMR (400 MHz, dmso-d6): δ 11.03 (s, 1H); 9.73 (s, 1H); 8.85 (s, 1H); 8.43 (d, J=5.2 Hz, 1H); 7.75 (d, J=8.8 Hz, 2H); 7.72 (d, J=8.8 Hz, 2H); 7.46 (s, 1H); 7.09 (d, J=5.2 Hz, 1H); 5.70 (m, 1H); 2.45 (s, 3H); 1.45 (d, J=6.8 Hz, 6H).

Provenance & Evidence