FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:32])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:31])[CH:18]=2)[CH:13]=1.[CH2:33]([S:35](Cl)(=[O:37])=[O:36])[CH3:34].C(N(CC)CC)C>ClCCl>[CH3:8][O:9][C:10](=[O:32])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([S:35]([CH2:33][CH3:34])(=[O:37])=[O:36])[CH2:27][CH2:26]2)=[O:24])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:31])[CH:18]=2)[CH:13]=1To a solution of [6-fluoro-3-methyl-4-(piperazine-1-carbonyl)-naphthalen-2-yl]-acetic acid methyl ester trifluoroacetate (45.8 mg, 0.10 mmol) and ethanesulfonyl chloride (14 μL, 0.15 mmol) in dichloromethane was added triethylamine (306 μL, 2.2 mmol). The resulting mixture was stirred at room temperature overnight, and concentrated in vacuo. The residue was purified by column chromatography (gradient elution with 20-40% ethyl acetate in petroleum ether) to afford [4-(4-ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (38 mg, 87%) as a white solid.
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