2,4,6-Trimethylaniline → HCID 44308664, compound

Participants

Reaction Steps

Diisopropylethyl amine (400 μL, 2.2 mmol) was added to a stirred suspension of compounds 179C and 180C (328 mg, 1 mmol), 2,4,6-trimethylaniline (170 μL, 1.1 mmol) and benzotriazolo-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (Castro's reagent, 485 mg, 1.1 mmol) in dichloromethane (5 mL). The solution was stirred at RT for 18 h, filtered and dried to obtain a mixture of intermediate benzotriazolo-esters (400 mg) which was dissolved in dimethylformamide (5 mL) and 2,4,6-trimethylaniline (560 μL, 4 mmol) was added. The solution was heated to 50° C. for 72 h, cooled and diluted with EtOAc (100 mL) and water (100 mL). The EtOAc layer was separated, washed with 1 N aq. HCl solution (100 mL, 3×), brine (50 mL), dried (MgSO4), filtered and concentrated. The orange-yellow solid was dissolved in dimethylsulfoxide (1 mL) and diluted with methanol (5 mL), followed by water (5 mL). The solution was let stand at RT for several hours. The precipitated solid was filtered, washed with water (20 mL), dried and then recrystallized from DMSO—MeOH—H2O mixture to obtain the pure title compound 179D (45 mg, 10%).

Provenance & Evidence