CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:18][P-](F)(F)(F)(F)F.F[C:26]1[CH:27]=[CH:28][C:29]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[C:30]([CH:34]=1)[C:31](O)=[O:32].C(N(CC)CC)C.O.[Cl-].[Na+].O.CN([CH:54]=[O:55])C>>[F:18][C:28]1[C:29]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[C:30]([CH:34]=[CH:26][CH:27]=1)[C:31]([O:55][CH3:54])=[O:32]HATU (105.8 mg, 0.278 mmol) was added to a solution of 5-fluoro-2-(methylsulfonamido)benzoic acid (57.1 mg, 0.246 mmol) in 3 mL of anhydrous DMF at room temperature. After 15 min of stirring, intermediate 6 (44.8 mg, 0.182 mmol) was added followed immediately by triethylamine (0.040 mL, 0.288 mmol). Reaction mixture stirred at room temperature for 24 hours under argon. Mixture was then poured into a mixture of 40 mL of 1:1 water/brine and extracted three times with 40 mL of ethyl acetate. The combined organic layers were washed with 50 mL of 1:1 water/brine, dried (MgSO4), filtered, and concentrated under reduced pressure leaving a residue. Product was purified by silica gel column chromatography (0-10% Methanol in Dichloromethane) and then prep HPLC (15-100% Acetonitrile (with 0.1% trifluoroacetic acid) in water (with 0.1% trifluoroacetic acid)) to yield compound 11 (61 mg, 58%) as a white solid, trifluoroacetate salt, after lyophilization.
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