Acetic Anhydride → HCID 53476279, compound

Participants

Reaction Steps

To solution of acetic anhydride (150 μL, 1.17 mmol) in formic acid (2 mL) stirred at RT for 20 min was added in one portion 1 (150 mg, 0.296 mmol). After 2 hr, 200 μL of acetic anhydride (1.57 mmol) were added dropwise. The reaction mixture was stirred at RT overnight, quenched by addition of MeOH and concentrated. The residue was purified by Biotage (SNAP 25 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20 CV, then 10/90 over 5 CV), to afford the title compound 6 (96 mg, 0.18 mmol, 76% yield) as an off-white fluffy solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): mixture of rotamers, 8.75 (s, 1H), 8.60-8.50 (m, 2H), 8.37 and 8.34 (2s, 1H), 8.32-8.23 (m, 114), 8.15 (s, 1H), 7.90-7.77 (m, 1H), 7.73 (dd, J=13.5, 2.5 Hz, 1H), 7.38 (t, J=9.0 Hz, 1H), 7.20 (bd, J=10.2 Hz, 1H), 6.67-6.58 (m, 2H), 4.60 and 4.56 (2s, 2H), 3.46-3.36 (m, 4H), 3.21 and 3.19 (2s, 3H), 2.59-2.51 (m, 1H), 0.70-0.60 (m, 2H), 0.47-0.38 (m, 2H). MS (m/z): 536.4 (M+H).

Provenance & Evidence