Triethylamine → HCID 131719554, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-amino-3-(N-methyl-N'-piperazinyl) benzene (140 mg) in anhydrous tetrahydrofuran (20 ml) at 0° C., under an atmosphere of nitrogen, was added triphosgene (71 mg). After 2 min, triethylamine (260 μl) was added dropwise and the mixture stirred at 0° C. for 5 min then at room temperature for 10 min. The mixture was then cooled back to 0° C. and a solution of crude 3(R,S)-amino-5-cyclohexyl-1,3-dihydro-1-propyl-2H-1,4-benzodiazepin-2-one (150 mg) in anhydrous tetrahydrofuran (5 ml) dropwise. The mixture was stirred at 0° C. for 5 min then at room temperature for 10 min. The mixture was filtered and the filtrate evaporated in vacuo. The residue was partitioned between ethyl acetate (30 ml) and water (30 ml) and an undissolved solid filtered off. The organic phase from the filtrate was separated and the aqueous phase washed once more with ethyl acetate (10 ml). The combined organic layers were washed with brine (20 ml), dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel using 95:5:1 dichloromethane:methanol:ammonia as the solvent. After trituration with ether the title urea (77 mg) was isolated as a white solid. Mp 255°-257° C. 1H NMR (360 MHz, D6 -DMSO) δ 0.73 (3H, t, J=7.3 Hz), 0.92 (1H, m), 1.07-1.90 (11H, m), 2.19 (3H, s), 2.39-2.42 (4H, m), 2.95 (1H, m), 3.02-3.05 (4H, m), 3.62-3.67 (1H, m), 4.16-4.22 (1H, m), 5.02 (1H, d, J=8.6 Hz), 6.49 (1H, dd, J=8 and 1.5 Hz), 6.01 (1H, d, J=8 and 1.5 z), 7.03 (1H, t, J=8 Hz), 7.11 (H, m), 7.21 (1H, d, J=8.5 Hz), 7.39 (1H, m), 7.62-7.63 (2H, m), 7.76 (1H, d, J=7.9 Hz), 8.82 (1H, s).

Provenance & Evidence