[CH3:1][O:2][C:3](=[O:24])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([C:11](=[N:21][OH:22])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:5]=1F.[H-].[Na+]>CN(C=O)C.O.C(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1[C:5]2[O:22][N:21]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=3)[C:6]=2[CH:7]=[CH:8][C:9]=1[Cl:10])=[O:24]To a solution of methyl-6-chloro-3-(N-(4-ethylphenyl)-N′-hydroxycarbamimidoyl)-2-fluorobenzoate (225 mg, 641 μmol) in DMF (6.4 ml) chilled to 0° C. was added NaH (17 mg, 706 μmol) in one portion. The yellow solution evolved gas and immediately turned a dark orange color. After 20 min, the mixture was diluted with H2O and DCM, the layers were separated and the aqueous layer was extracted with DCM (2×). The organic layers were combined and washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound as a light brown solid, which was used for the next step without further purification.
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