Triethylamine → N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(methylsulphonylaminocarbonyl)phenyl]urea

Participants

Reaction Steps

The rifle compound was prepared in the same way as that described in Example 11, Step 4, using 5-cyclohexyl-1,3-dihydro- 1-methyl-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (0.5 g, 1.2 mmol), triethylamine (0.16 ml, 1.2 mmol), dimethylformamide (10 ml) and 1-(methylsulphonylaminocarbonyl)-3-nitrobenzene (0.25 g, 1.2 mmol). After recrystallisation from ethanol, the compound (0.15 g, 26%) was afforded as a pale beige solid. mp 175° C (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 0.88 (1H, m), 1.10-1.67 (7H, m), 1.72-1.81 (1H, m), 1.91 (1H, m), 2.95 (1H, m), 3.32 (3H, s), 3.34 (3H, s) 5.08 (1H, d, J=8.2 Hz), 7.37 (3H,m), 7.47 (1H, d, J=7.9 Hz), 7.56 (2H, m), 7.64 (1H, dd, J=7.0 and 7.0 Hz), 7.75 (1H, d, J=7.9 Hz), 7.91 (1H, s), 9.21 (1H, s), 12.07 (1H, brs).

Provenance & Evidence