Triphosgene → ((6-chloropyridin-3-yl)methyl)-3-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-8-yl)urea

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Reaction Conditions

Reaction Steps

Commercially available (6-chloropyridin-3-yl)methanamine (800 mg, 5.61 mmol) was dissolved in 40 ml of AcOEt and at 0° C. triphosgene (1.54 g, 5.6 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1f (900 mg, 4.51 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 9.5/MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1×40 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 180 mg of a beige solid. Yield=12% 1HNMR (DMSO, 200 MHz) δ 4.31 (2H, d, J=5.6 Hz), 4.60 (2H, s), 6.47 (1H, dd), 6.81 (1H, t), 7.40 (1H, t), 7.50 (1H, d, J=8.2 Hz), 7.72 (2H, m), 8.13 (1H, bs), 8.34 (1H, bs), 10.66 (1H, bs); [M+1] 332.8 (C15H13ClN4O3 requires 332.74).

Provenance & Evidence