Lithium hydroxide, monohydrate → 6-((5-Chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinamido)methyl)nicotinic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:27][CH:26]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][N:14]=2)CC1)=[O:8].O.[OH-].[Li+]>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:25][CH:26]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[CH2:27]2)=[C:6]([CH:23]=1)[C:7]([NH:9][CH2:10][C:13]1[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=1)=[O:8]Participants
3
Conditions
- Temperature
- 70 °C
Procedure
To a solution of methyl 6-((5-chloro-2-(3-(3-fluorophenoxy)azetidin-1-yl)nicotinamido)methyl)nicotinate (D159) (22 mg, 0.045 mmol) in a mixture 1-4dioxane/water (1.5 ml/0.5 ml), lithium hydroxide hydrate (2.8 mg, 0.067 mmol) was added. The reaction mixture was heated to 70° C. for 1 h. After solvent evaporation the residue was taken in water (10 ml) and 1M HCl (10 ml) and extracted with ethylacetate (2×20 ml). Collected aorganics after solvent evaporation afforded the title compound (E24) (19 mg)