Diisopropylethylamine → HCID 68530418, compound

Participants

Reaction Steps

To a solution of [4-(4-iodo-phenyl)-1-methyl-piperidin-4-yl]-methylamine (0.20 g, 0.606 mmol) in CH2Cl2 (2 mL) under Ar was added 2,4-difluorophenylisocyanate (0.08 mL, 0.667 mmol, 1.1 eq.) and DIEA (0.106 mL, 0.606 mmol, 1 eq.). The mixture was stirred at room temperature for 16 h then diluted with EtOAc (25 mL) and washed with H2O (20 mL) and saturated brine (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give a yellow oil which was purified by flash column chromatography by eluting with 3% MeOH/CH2Cl2 (1% TEA) to furnish 1-(2,4-difluoro-phenyl)-3-[4-(4-iodo-phenyl)-1-methyl-piperidin-4-yl-methyl]-urea as a white solid (0.211 g, 0.435 mmol, 72%). 1H NMR (300 MHz, CDCl3): δ 7.84 (br.d, NH), 7.68 (d, 2H), 7.36 (s, 1H), 7.11 (d, 2H), 6.87 (d, 2H), 5.32 (br.s., NH), 3.40 (s, 2H), 2.66 (m, 4H), 2.28 (s, 3H), 2.10 (m, 2H), 1.96 (m, 2H), 1.14 (t, 3H). MS (ESI): 486.1,487.0 (M+1).

Provenance & Evidence