Cl.[CH3:2][NH:3][O:4][CH3:5].C(N(CC)CC)C.[F:13][C:14]1[N:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1.O>ClCCl>[F:13][C:14]1[N:19]=[CH:18][C:17]([C:20]([N:3]([O:4][CH3:5])[CH3:2])=[O:21])=[CH:16][CH:15]=1To a 250-mL round-bottom flask containing N,O-dimethyl hydroxylamine hydrochloride (3.5 g, 35.9 mmol) and triethylamine (15.0 mL, 108 mmol) was added a solution of 6-fluoropyridine-3-carbonyl chloride (5.70 g, 35.7 mmol, Intermediate 21, step a) in dichloromethane (200 mL) dropwise. The resulting mixture was stirred for 12 hours at room temperature, and 20 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with 2×100 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by chromatography (silica gel column, 100:1 CHCl3/MeOH) to give the title compound as a white solid.
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