[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:16][NH:17][O:18][CH3:19].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CCOC(C)=O.O>[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([N:17]([O:18][CH3:19])[CH3:16])=[O:5]To a suspension of 2-chloro-6-trifluoromethyl-nicotinic acid (200 mg, 0.88 mmol) and N,O-dimethylhydroxylamine hydrochloride (95 mg, 0.97 mmol) in CH2Cl2 (3 mL) was added N-methylmorpholine (0.106 ml, 0.97 mmol). The mixture was stirred for 5 minutes, to which was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (185 mg, 0.97 mmol). The mixture was stirred for 3 hours at room temperature, and then diluted with EtOAc and water. The organic layer was washed with 1N HCl, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The product was vacuum dried to yield the 2-chloro-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (220 mg, 92%).
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