Dichloromethane → 1-(5-tert-butyl-2-p-tolyl-2H-pyrazole-3-yl)-3-{6-[4-(2,6-difluoro-benzoyl)-piperazin-1-yl]pyridin-3-yl}-urea

Participants

Reaction Steps

Place 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(6-piperazin-1-yl-pyridin-3-yl)-urea (48 mg, 0.111 mmol), 2,6-difluorobenzoic acid (21 mg, 0.133 mmol), and 4-N,N-dimethylaminopyridine (3 mg, 0.022 mmol) in acetonitrile (5 mL). Add O-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (50 mg, 0.133 mmol) and heat to 70° C. for 19 hours. Cool to room temperature and add CH2Cl2 and water. Separate organic layer and extract aqueous with CH2Cl2 (2×25 mL). Combine organics, dry over Mg2SO4, filter, and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with 0-60% EtOAc:hexane to yield the title compound. LCMS(ES): m/z=574.2 [M+H].

Provenance & Evidence