Formic Acid → HCID 178492380, compound

Participants

Reaction Steps

To a stirring solution of 110 mg (0.17 mmol) of 2-[3-(1-Benzyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl) acetamide in 15 mL of a 10% solution of formic acid in absolute ethanol is added 100 mg of 10% palladium on carbon. The resulting black suspension is heated at reflux for 24 h, then cooled to RT. The reaction mixture is filtered through Celite to remove the catalyst and the solvent removed in vacuo. Purification of the residue by gradient silica gel flash column chromatography using hexane/EtOAc 3/2 up to 2/3 as eluent followed by further purification via reverse phase MPLC using a C-18 column and 60% acetonitrile/40% H2O as eluent and lyophilization afforded 62 mg of the title compound as a white amorphous solid: 1H NMR (CDCl3, 300 MHz) δ7.81 (d, 1H, J=8.0), 7.41-6.90 (m, 17H), 5.00 (m, 1H), 4.23 (m, 3H), 3.84 (s, 3H), 3.79 (d, 1H, J=7.9), 3.61 (dd, 1H, J=5.8, 16.1), 1.06 (m, 6H); low resolution MS (FAB)m/e 588 (MH+), 423, 223; Anal. (C35H33N5O4.H2O) Calcd. C, 70.45; H, 5.91; N, 11.74 Found C, 70.62; H, 5.76; N, 11.78.

Provenance & Evidence