Acetamide → HCID 11201276, compound

Participants

Reaction Conditions

Reaction Steps

1-[4-(6-Chloro-pyrimidin-4-yloxy)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea (compound of Example 56) (100 mg, 0.245 mmol)1 acetamide (40 mg1 0.678 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-xanthrene (9 mg), and tris(dibenzylideneacetone)dipalladium (6 mg) dissolved in dioxane (3 mL) are stirred at 55° C. under Ar for 8 h. After evaporating the solvent under reduced pressure, the residue is partitioned between H2O (60 mL) and AcOEt (200 mL). The organic phase is separated, dried (MgSO4) and concentrated under reduced pressure. The product is purified by preparative thin layer chromatography (four 20×20 cm silica gel plates, acetone/CH2Cl2=3:7): M+H=431.9; Rf (acetone/CH2Cl2=3:7): 0.29; 1H-NMR (400 MHz, DMSO-d6): 10.85 (s, 1H, pyrimidinyl), 9.03/8.84 (s/s, 1H/1H, urea), 8.45 (s, 1H, NH), 7.98 (s, 1H, pyrimidinyl), 7.56 (d, 8.5 Hz, 1H, phenyl-CF3), 7.50 (d/s, 9.0 Hz, 2H/1H, phenyl/phenyl-CF3), 7.49 (t, 1H, phenyl-CF3), 7.29 (d, 8.5 Hz, 1H, phenyl-CF3), 7.06 (d, 9.0 Hz, 2H, phenyl), 7.39 (d, 8.5 Hz, 2H), 7.13 (s, 1H), 7.11 (d, 8.5 Hz, 2H), 6.86 (d, 8.5 Hz, 2H), 5.94 (s, 1H, pyrimidinyl), 2.09 (s, 3H, CH3).

Provenance & Evidence