[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]To a solution of methyl 5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1-yl)nicotinate (D85) (37 mg, 0.104 mmol) in a mixture 3:1 1,4-dioxane/water (4 ml), 1M NaOH (0.157 ml) was added and the resulting mixture was stirred 12 h at 60° C. After cooling the reaction mixture was acidified to pH 1 by addition of 1M HCl. The resulting precipitate was collected by filtration and afforded the title compound (D118) (35 mg).
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