Lithium hydroxide, monohydrate → 5-(2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

HRID 1802199Notes

Reaction equation

HRID 1802199 reaction equation
[CH:1]([C:4]1[N:26]=[C:7]2[CH:8]=[C:9]([NH:12][C:13]([C:15]3[N:19]([CH3:20])[N:18]=[CH:17][C:16]=3[C:21]([O:23]CC)=[O:22])=[O:14])[CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].O.[OH-].[Li+]>CO.O>[CH:1]([C:4]1[N:26]=[C:7]2[CH:8]=[C:9]([NH:12][C:13]([C:15]3[N:19]([CH3:20])[N:18]=[CH:17][C:16]=3[C:21]([OH:23])=[O:22])=[O:14])[CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67775033ethyl 5-(2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 677767115-(2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acidYield 93.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl 5-(2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate (330 mg, 926 μmol) and lithium hydroxide monohydrate (155 mg, 3.7 mmol) in methanol (6 ml) and water (2 ml) is stirred for 18 hours at 25° C. The solvents are evaporated, the white residue is dissolved in water and acidified with 37% aqueous hydrochloric acid. The precipitated white solid is collected by filtration, washed with water and dried affording 5-(2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (285 mg, 93.7%) as a white solid. Mp.: >250° C. MS: m/z=327.3 (M−H+).

Workup

  1. customThe solvents are evaporated
  2. dissolutionthe white residue is dissolved in water
  3. filtrationThe precipitated white solid is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a653c65f8da54a0780090efa765a3eb6
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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