Triethylamine → HCID 57274307, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-cyclohexyl-1,3-dihydro-1-methyl-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (22 mg, 0.51 mmol) in anhydrous dimethylformamide (3 ml) under nitrogen was added triethylamine (70 μl, 0.51 mmol). The solution was stirred for 5 min before adding a solution of 6-amino-3,4-dihydro-2,2-dioxo-4-oxo-1H-2,3-benzothiazine (107 mg, 0.51 mmol) and triethylamine (70 μl, 0.51 mmol) in anhydrous dimethylformamide (3 ml) and acetonitrile (10 ml). The resulting solution was heated at 50° C. for 10 h, before removing the solvents in vacuo and partitioning the residue between 20% aqueous acetic acid (5 ml) and ethyl acetate (20 ml). The aqueous phase was re-extracted with more ethyl acetate (2×20 ml) and the combined organic extracts dried (Na2SO4) and evaporated in vacuo. The resulting yellow oil was stirred with diethyl ether (10 ml) to give a pale yellow solid. This was purified by flash chromatography on silica gel, eluting with 5-20% methanol/dichloromethane, to afford the title compound (95 mg, 37%) as a pale yellow solid, which was recrystallised from isopropanol/dichloromethane. mp>300° C. 1H NMR (360 MHz, D6-DMSO) δ 0.93 (1H, m), 1.12-1.64 (7H, m), 1.76 (1H, m), 1.89 (1H, m), 2.93 (1H, m), 3.29 (3H, s), 3.96 (2H, s), 5.08 (1H, d, J=8.4 Hz), 7.09 (1H, d, J=8.3 Hz), 7.24 (1H, d, J =8.5 Hz), 7.38 (1H, t, J=7.9 Hz), 7.49 (1H, dd, J=8.2 and 2.4 Hz), 7.55 (1H, d, J=8.3 Hz), 7.63 (1H, t, J=7.9 Hz), 7.74-7.76 (2H, m), 9.04 (1H, s). MS (FAB) 508 (M-1).

Provenance & Evidence