Triphosgene → 1-(4-(Trifluoromethyl)-2-(piperidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea

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Reaction Conditions

Reaction Steps

Amine 2c (350 mg, 1.33 mmol) (Scheme 7) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (395 mg, 1.33 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (100 mg, 0.66 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 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 40 mg of a white solid. Yield=14% 1HNMR (DMSO, 400 MHz) δ 1.55 (2H, m), 1.68 (4H, m), 2.85 (4H, m), 4.43 (2H, d, J=5.6 Hz), 6.88 (1H, t), 6.98 (2H, m), 7.05 (1H, m), 7.31 (1H, s), 7.42 (1H, d), 7.52 (1H, d, J=8 Hz), 8.52 (1H, s), 11.00 (1H, bs); [M+1] 435.3 (C21H21F3N4O3 requires 434.41).

Provenance & Evidence