N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide → N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-propyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide

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Reaction Steps

To a stirring solution of 40 mg (71.7 mmol) of N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide, prepared as in Example 11, in 3 mL absolute ethanol is added 10 mg of 10% palladium on carbon. The reaction vessel is placed on a Parr hydrogenation apparatus, evacuated, and then pressurized with H2 gas to 40 psi and shaken for 2 h at RT. The reaction mixture is filtered through Celite to remove the catalyst and the solvent removed in vacuo. Purification of the resulting material via reverse phase MPLC using a C-18 column and 70% acetonitrile/30% H2O with 0.1% TFA as eluent followed by lyophilization afforded 29 mg of the title compound as a white amorphous solid: 1H NMR (CDCl3, 300 MHz) δ7.49-6.96 (m, 19H), 6.72 (d, 1H, J=8.0), 5.09 (m, 1H), 4.38 (d, 1H, J=16.3), 3.92 (d, 1H, J=16.3), 2.28 (m, 2H), 1.67-1.50 (m, 6H), 1.34 (m, 1H), 1.12 (m, 6H); low resolution MS (FAB)m/e 560 (MH+), 425, 397, 223.

Provenance & Evidence