Diisopropylethylamine → HCID 86604270, compound

Participants

Reaction Steps

To a stirred solution of 4-methyl-3-(1-{[4-(2,4,5-trifluorophenoxy)phenyl]methyl}(4-piperidyl))phenylamine (271 mg, 0.64 mmol) in dimethylformamide (15 mL) was added 2-[(tert-butoxy)-N-methylcarbonylamino]acetic acid (361 mg, 1.91 mmol) followed by O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 728 mg, 1.91 mmol) and diisopropylethylamine (328 mg, 2.54 mmol). After stirring at room temperature for 21 h, the reaction mixture was partitioned between CH2Cl2 (30 mL) and saturated aqueous NaHCO3 (30 mL). The organic layer was washed with water (3×30 mL) and brine (30 mL), dried over MgSO4 and concentrated in vacuo provided the crude product. Purification on silica gel (silica gel 60, 40 mL) eluting with CH2Cl2 then 3% methanol in CH2Cl2 to give 2-[(tert-butoxy)-N-methylcarbonylamino]-N-[4-methyl-3-(1-{[4-(2,4,5-trifluorophenoxy)phenyl]methyl}(4-piperidyl))phenyl]acetamide (345 mg, 0.58 mmol, 90% yield) as a white solid. LCMS (method B): 2.81 min, 598.3 (M+H)+.

Provenance & Evidence