N-bromobutanimide → HCID 86649133, compound

Participants

Reaction Steps

To a suspension of the product from Example 51 (455 mg, 0.534 mmol) in CH2Cl2 (2.7 mL) was added a mixture of 1-bromopyrrolidine-2,5-dione (95 mg, 0.534 mmol) in CH2Cl2 (2.7 mL). The mixture was stirred overnight at room temperature then concentrated under reduced pressure and triturated with diethyl ether to provide a mixture of compounds that was subjected to reverse phase HPLC purification eluted with a gradient of 60-100% MeOH in 10 mM ammonium acetate to afford the title compound (84 mg, 17% yield). 1H NMR (free base) (400 MHz, DMSO-D6) δ 10.06 (s, 1H), 10.02 (s, 1H), 7.46 (d, J=8.7, 2H), 7.41 (d, J=8.7, 2H), 7.30 (d, J=7.7, 2H), 7.15-7.03 (m, 6H), 6.98 (d, J=8.7, 2H), 6.53 (s, 1H), 4.45-4.33 (m, 2H), 4.01 (t, J=7.7, 2H), 3.85-3.73 (m, 2H), 3.66-3.54 (m, 2H), 3.51 (s, 6H), 2.20-2.05 (m, 2H), 2.03-1.77 (m, 8H), 0.97-0.79 (m, 12H). MS (ESI; M+H) m/z=933.

Provenance & Evidence