Ethyl Acetate → 1-(4-methyl-2-(piperidin-1-yl)benzyl)-3-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-8-yl)urea

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Reaction Conditions

Reaction Steps

Amine 2bh (1.08 g, 5.3 mmol) (Scheme 8) was dissolved in 40 ml of AcOEt and at 0° C. triphosgene (1.56 g, 5.4 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 15 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1f (1 g, 5.46 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 1/petroleum ether 9). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1×30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 150 mg of a white solid. Yield=7% 1HNMR (DMSO, 200 MHz) δ 1.63 (6H, m), 2.25 (3H, s), 2.76 (4H, m), 4.28 (2H, d, J=5.4 Hz), 4.61 (2H, s), 6.46 (1H, dd, J=7.8 Hz, J′=1.4 Hz), 6.81 (3H, m), 7.12 (2H, m), 7.75 (1H, dd, J=8.2 Hz, J′=1.6 Hz), 8.11 (1H, s), 10.66 (1H, bs); [M+1] 395.0 (C22H26N4O3 requires 394.5).

Provenance & Evidence