Lithium hydroxide, monohydrate → 5-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid

HRID 402412Notes

Reaction equation

HRID 402412 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:13]=[N:12][C:11]([O:14][CH2:15][C:16]2[N:17]([CH3:28])[N:18]=[N:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:10][N:9]=1)=[O:7]>O.C1COCC1>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]2[N:19]=[N:18][N:17]([CH3:28])[C:16]=2[CH2:15][O:14][C:11]2[N:12]=[CH:13][C:8]([C:6]([OH:7])=[O:5])=[N:9][CH:10]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 674979845-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 674984675-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acidYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (107 mg, 2.55 mmol) in water (3.2 mL) was added dropwise to a suspension of 5-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester (438 mg, 1.27 mmol) in THF (1.8 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 (1N), and the resulting precipitate filtered off to afford the title product (403 mg, 96%) as a white solid. MS: m/e=328.1 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-09e7961abe874486806d274f72c6ada9
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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