Acetic Anhydride → HCID 53251278, compound

Participants

Reaction Steps

Acetic anhydride (1 mL; Fischer) was added dropwise to a solution of the product of Example 6C (45 mg, 0.16 mmol) in acetic acid (1 mL). The reaction mixture was stirred at room temperature for 10 minutes and then concentrated under vacuum. The resulting residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 20-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (400 MHz, methanol-d4) (1:1 mixture of amide rotamers observed) δ ppm 2.23 and 2.24 (two s, 3H; amide rotamers), 2.54 (s, 3H), 2.90 and 2.99 (two t, J=5.8 Hz, 2H; amide rotamers), 3.91 and 3.99 (two t, J=5.8 Hz, 2H; amide rotamers), 4.74-4.77 (m, 2H), 7.05 and 7.06 (two t, J=7.6 Hz, 2H; amide rotamers), 7.24 (d, J=16.5 Hz, 1H), 7.31 (d, J=8.2 Hz, 1H), 7.36 and 7.39 (two dd, J=7.8, 0.8 Hz, 1H; amide rotamers), 7.42 and 7.43 (two d, J=7.3 Hz, 1H), 7.67 (d, J=16.5 Hz, 1H), 8.00 and 8.02 (two t, J=1.8 Hz, 1H), 8.61 (d, J=2.1 Hz, 1H); MS (APCI) m/z 332 (M+H)+.

Provenance & Evidence