[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.C([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])C.Cl.Cl.[F:29][CH2:30]N1CCNCC1.[NH3:37]>ClCCl.CO.CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]([C:5]([N:22]2[CH2:23][CH2:24][NH:37][CH:26]([CH2:30][F:29])[CH2:25]2)=[O:7])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]A stirred suspension of 3-fluoro-4-nitrobenzoic acid (2 g, 10.8 mmol) in dichloromethane (30 mL) was cooled to 0° C. (ice/water bath). Oxalylchloride (1.648 g, 12.97 mmol) was added followed by N-methylpyrrolidinone (1 mL) to achieve a solution. The reaction mixture was stirred at 0° C. for 1 hour and then was concentrated under reduced pressure. The residue was azeotroped with dichloromethane (×3). The residue was redissolved in dichloromethane (20 mL) and cooled to 0° C. before the addition of triethylamine (64.8 mmol, 6.56 g) and 1-(fluoromethyl)piperazine dihydrochloride (10.8 mmol, 2.064 g). The reaction mixture was allowed to warm to room temperature and stir for 1 hour before being applied to a strong cation exchange column. The crude product was released from the column using 2M ammonia in methanol and purified using silica chromatography (4% methanol/dichloromethane) to give the title compound (444 mg). MS (ESI) m/z 286.4 [M+H]+
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