Triethylamine → N-[3(S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo1H-1,4-benzodiazepin-3-yl]N'-[3-(phenylsulphonylaminocarbonyl)phenyl]urea

Participants

Reaction Steps

The title compound was prepared in the same way as that described in Example 33, Step 4, using 1-(phenylsulphonylaminocarbonyl)-3-aminobenzene (0.30 g, 1.08 mmol) [Example 14, Step 2]), triphosgene (107 mg, 0.36 mmol), triethylamine (0.45 ml, 3.23 mmol), 3(S)-amino-5-cyclohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (0.2 g, 0.74 mmol) and tetrahydrofuran (30 ml). After trituration with diethyl ether, the title compound (248 mg, 59%) was afforded as a colourless solid with >99% e.e. mp 180° C. (dec.). 1H NMR (360 MHz, D6-DMSO) δ 0.82-0.98 (1H, m), 1.08-1.65 (7H, m), 1.75-1.83 (1H, m), 1.88-1.96 (1H, m), 2.90-3.00 (1H, m), 3.31 (3H, s), 5.06 (1H, d, J=8.3 Hz), 7.30-7.36 (2H, m), 7.37-7.41 (2H, m), 7.49-7.56 (2H, m), 7.60-7.65 (3H, m), 7.68-7.76 (2H, m), 7.84 (1H, s), 7.96-7.99 (2H, m), 9.17 (1H, s), 12.46 (1H, brs). [α]D +9.4° (c=0.37, CH3OH).

Provenance & Evidence