Acetic Anhydride → HCID 131721083, compound

Participants

Reaction Steps

300 mg (0.505 mmol) 2-[3-(6-Fluoro-1H-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5,-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-(4-fluoro-phenyl)-N-isopropyl-acetamide, prepared as in Example 63, is dissolved in 15 mL Acetic anhydride and heated at reflux 1 h. The solvent is removed in vacuo and the residue purified by preparative HPLC on a Delta-Pak C-18 column eluted from 35% to 60% CH3CN in H2O with 0.1% TFA buffer over 30 minutes at 150 mL/min. The appropriate fraction is frozen and lyophilized to give 144 mg (0.226 mmol) of the title compound as a white lyophilizate: 1H NMR (CDCl3, 300 MHz) δ8.04 (m, 1H), 7.76 (m, 1H), 7.50 (d, 1H, J=8.0), 7.39-7.08 (m, 12H), 6.98 (d, 1H, J=7.8), 5.02 (m, 1H), 4.32 (d, 1H, J=16.6), 4.30 (t, 1H), 4.10 (d, 1H, J=16.6), 3.75 (m, 1H), 3.57 (m, 1H), 2.63 (s, 3H), 1.08 (m, 6H); low resolution MS (FAB) m/e 636.1 (MH+); TLC Rf =0.30 (EtOAc/Hexanes, 1:2).

Provenance & Evidence