Lithium hydroxide, monohydrate → 6-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-nicotinic acid

HRID 1161344Notes

Reaction equation

HRID 1161344 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:37])[CH:12]([N:19]2[C:23]3[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:22]=3[N:21]=[C:20]2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:6][CH:5]=1.O.[OH-].[Li+]>O.O1CCOCC1>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C:20]2[N:19]([CH:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:38])=[O:2])=[CH:5][N:6]=3)=[O:37])[C:23]3[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:22]=3[N:21]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 686452646-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-nicotinic acid methyl ester

Product 1

HCID 441987326-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-nicotinic acidYield 95.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-nicotinic acid methyl ester (24 mg, 0.04 mmol) was dissolved in water (0.5 ml) and dioxane (0.5 ml). Lithium hydroxide monohydrate (9 eq, 17 mg) was added and the mixture stirred 3 h at room temperature. The dioxane was removed under reduced pressure and the residue acidified to pH2 with 3M aqueous hydrochloric acid. The precipitate was filtered to afford the title compound as a white solid (20 mg, 84%).

Workup

  1. customThe dioxane was removed under reduced pressure
  2. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-6cac8ab46fe547d0bd486a018cb8fb74
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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