F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(N(CC)CC)C.[NH2:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.NC1CCCCO1.Cl>C(O)C.O>[O:25]1[CH2:26][CH2:27][CH:22]([NH:21][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])[CH2:23][CH2:24]14-Fluoro-3-nitrobenzoic acid (126.4 g, 0.68 mol) was dissolved in ethanol (880 mL). Triethylamine (82.6 g, 0.82 mol), 4-aminotetrahydropyran (82.7 g, 0.81 mol) were added in turn dropwise, and after the additions the reaction solution was heated to reflux. After refluxing for 5 h, triethylamine (8.3 g, 82 mmol), aminotetrahydropyran (8.3 g, 81 mmol) were added, and this was refluxed for a further 9 hours. After the reaction mixture was allowed to cool to room temperature, 2N HCl (880 mL) and water (880 mL) were added and after stirring for awhile, the solid obtained was filtered off. This was forced air-dried at 60° C. to yield the title compound (183.3 g, quant.) as a yellow solid.
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