Triethylamine → HCID 131719555, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-cycloheptyl-1,3-dihydro-1-(2-methylpropyl)-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (150 mg) in anhydrous dimethylformamide (3 ml), under an atmosphere of nitrogen, was added triethylamine (42 μl). After 5 min a solution of 1-amino-3-(N-methyl-N'-piperazinyl)benzene (64 mg) in anhydrous dimethylformamide (2 ml) was added and the solution heated at 50° C. for 1 h. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (20 ml) and water (20 ml). The undissolved solid was filtered off, washed with ethyl acetate and water, then triturated with anhydrous diethyl ether to yield the desired urea (87 mg) as a white solid. 1H NMR (360 MHz, D6 -DMSO) δ 0.66 (3H, d, J=6.6 Hz), 0.77 (3H, d, J=6.6 Hz), 1.20-1.80 (12H, m), 1.96-2.10 (1H, m), 2.20 (3H, s), 2.18-2.20 (4H, m), 3.03-3.05 (4H, m), 3.14-3.18 (1H, m), 3.62 (1H, dd, J=13.9 and 4.4 Hz), 4.13 (1H, dd, J=13.9 and 9.6 Hz), 5.00 (1H, d, J=8.5 Hz), 6.49 (1H, d, J=8.3 Hz), 6.61 (1H, d, J=7.7 Hz), 7.03 (1H, t, J=8.1 Hz), 7.11 (1H, m), 7.23 (1H, d, J=7.7 Hz), 7.37 (1H, dd, J=7 and 7 Hz), 7.59-7.68 (2H, m), 7.78 (1H, d, J=6.8 Hz), 8.84 (1H, s). MS (FAB) 545 (M+).

Provenance & Evidence