Boron tribromide → HCID 136116857, compound

Participants

Reaction Steps

To N-(4-chloro-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)-2-nitrophenyl)-4-(dimethylamino)benzamide (Example 14, 50 mg, 0.081 mmol) in 7 mL of DCM at −78° C. was added 0.24 mL of 1.0 M boron tribromide in DCM. The solution was stirred at room temperature for 16 hours. Solvent was evaporated in vacuo and the product was purified by preparative HPLC (acetonitrile/water, 10 mM NH4OAc) to give 42 mg of the title compound. 1H-NMR (CDCl3, 400 MHz): δ 11.52 (1H, s), 8.70 (1H, s), 8.30 (1H, s), 7.90 (2H, d, J=9.0 Hz), 7.45-7.33 (2H, m), 7.15-7.07 (1H, m), 7.04-6.95 (1H, m), 6.88 (2H, d, J=8.8 Hz), 4.07-4.00 (2H, m), 3.38 (4H, s), 3.12 (6H, s), 2.99 (2H, s), 2.57 (3H, s). HPLC/MS (Method G): (ES+) m/z (M+H)+=605; Rt=2.29 min.

Provenance & Evidence