Morpholine → 3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}-N-({4-(4-morpholinyl)-2-[(trifluoromethyl)oxy]phenyl}methyl)cyclohexanecarboxamide

Participants

Reaction Steps

A mixture of N-({4-bromo-2-[(trifluoromethyl)oxy]phenyl}methyl)-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide (60 mg, 0.116 mmol), morpholine (20.21 mg, 0.232 mmol), Pd2(dba)3 (5.31 mg, 5.80 μmol), BINAP (5.42 mg, 8.70 μmol) and cesium carbonate (76 mg, 0.232 mmol) in 1,4-Dioxane (2 ml) was irradiated via microwave reactor for 20 min at 170° C. The crude reaction mixture was passed through a 2 gram SCX ion-exchange column. The column was flushed with MeOH, then it was flushed with 2N NH3 in MeOH. The NH3 solution was collected and the solvent was evacuated to give a residue which was purified by preparative HPLC, resulting in 3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}-N-({4-(4-morpholinyl)-2-[(trifluoromethyl)oxy]phenyl}methyl)cyclohexanecarboxamide (15 mg, 0.022 mmol, 19%). MS (ES) m/e 524 [M+H]+.

Provenance & Evidence