Water → 5-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]N,N-dimethylpyridine-2-carboxamide

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Reaction Steps

Cyanuric chloride (85 mg, 0.46 mmol) was added to N,N-dimethylformamide (0.036 mL, 0.46 mmol) at room temperature. After the formation of a white solid (10 minutes), methylene chloride (2 mL) was added, followed by 5-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]-N,N-dimethylpyridine-2-carboxamide (115 mg, 0.330 mmol, from Example 11, step 3). After the addition, the mixture was stirred at room temperature overnight. Water was added, and then diluted with dichloromethane. The organic phase was washed with sat. NaHCO3 solution, water and brine, then dried over MgSO4, concentrated. The residue was purified on silica gel (eluting with 0 to 80% EtOAc in hexanes) to give the desired product (76 mg, 63%). LCMS calculated for C18H21Cl2N2O2 (M+H)+: m/z=367.1; Found: 367.0.

Provenance & Evidence