[N+:1]([C:4]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:5]=1[C:6]([NH:8][CH2:9][CH:10]=[O:11])=[O:7])([O-])=O.[C:20](C1C=CC2C(=O)NCC=NC=2C=1)(C)(C)C>CO.[Pd]>[C:16]([C:14]1[CH:13]=[CH:12][C:5]2[C:6](=[O:7])[NH:8][CH2:9][CH:10]([O:11][CH3:20])[NH:1][C:4]=2[CH:15]=1)([CH3:19])([CH3:18])[CH3:17]70 mg 10 wt % Pd on carbon was wetted with a small amount of methanol under argon. To this was added 717 mg (3 mmol) 2-nitro-4-tert-butyl-N-(2-oxo-ethyl)-benzamide dissolved in 20 mL methanol. The flask was evacuated and the atmosphere replaced with hydrogen gas using a balloon as ballast, and the mixture was hydrogenated for 3 hours. The reaction was filtered through celite under argon, the celite washed with ethyl acetate. Solvent was removed under vacuum to give a solid. NMR and LC/MS shows this to be a mixture of the title compound and 8-tert-Butyl-3,4-dihydro-benzo[e][1,4]diazepin-5-one as a one to one mixture, which was used without purification.
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