[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[C:4]2[O:12][C:13]([CH3:17])([CH3:16])[O:14][CH2:15][C:3]=12.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.[Cl-].[NH4+]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]2[CH:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[C:4]3[O:12][C:13]([CH3:17])([CH3:16])[O:14][CH2:15][C:3]=23)=[O:24])=[CH:21][CH:20]=1A mixture of methyl 5-amino-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate (23c) (70 mg, 0.25 mmol), 4-fluorobenzoyl chloride (35 μL, 0.27 mmol) and 4-dimethylaminopyridine in pyridine (1 mL) was stirred at room temperature overnight and a saturated solution of ammonium chloride was added. The reaction mixture was extracted with dichloromethane (3×25 mL) and the combined organic layers were dried (anh. Na2SO4), filtered and concentrated under reduced pressure to give methyl 5-(4-fluorobenzamido)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate (23d) as a white solid MS-ESI m/z 361 [MH]+.
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