Lithium hydroxide, monohydrate → 6-(4-(1-(2-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)-1H-imidazol-1-yl)nicotinic acid

HRID 1258925Notes

Reaction equation

HRID 1258925 reaction equation
O.[OH-].[Li+].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:15]([C:16]2[N:17]=[CH:18][N:19]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][N:22]=3)[CH:20]=2)=[C:14]([CH3:31])[N:13]=[N:12]1>O.C1COCC1.CO>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:15]([C:16]2[N:17]=[CH:18][N:19]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][N:22]=3)[CH:20]=2)=[C:14]([CH3:31])[N:13]=[N:12]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67954941HCID 67954941, compound

Product 1

HCID 679551606-(4-(1-(2-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)-1H-imidazol-1-yl)nicotinic acidYield 88.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (29 mg, 0.671 mmol) in water (1.3 mL) was added dropwise to a suspension of methyl 6-(4-(1-(2-fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)-1H-imidazol-1-yl)nicotinate (127 mg, 0.336 mmol) in THF (5 mL) and methanol (1 mL). The reaction mixture was then stirred at room temperature for 1 h and was then evaporated and the residue dissolved in water, acidified with HCl (1 N), and the resulting precipitate filtered off to afford the title product (108 mg, 88%) as a white solid. MS: m/e=363.3 [M−H]−.

Workup

  1. customwas then evaporated
  2. dissolutionthe residue dissolved in water
  3. filtrationthe resulting precipitate filtered off

Sources & evidence

ORD record
ord-6f48c008acbb4a069a524fa546291923
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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