Methanol → 1-(4-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea

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Reaction Conditions

Reaction Steps

(4-(pyrrolidin-1-yl)phenyl)methanamine 2l (774 mg, 4.4 mmol) was dissolved in 40 ml of AcOEt and at 0° C. triphosgene (1.3 g, 1 equiv.) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (660 mg, 4.4 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 (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 250 mg of a white solid. Yield=16% 1HNMR (DMSO, 200 MHz) δ 1.92 (4H, m), 3.17 (4H, m), 4.17 (2H, d, J=5.6 Hz), 6.58 (4H, m), 6.84 (2H, m), 7.12 (2H, d, J=8.6 Hz), 8.16 (1H, bs), 9.93 (1H, bs), 10.58 (1H, bs); [M+1] 352.3 (C19H21N5O2 requires 351.4).

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