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

HRID 1802250Notes

Reaction equation

[Br:1][C:2]1[N:24]=[C:5]2[CH:6]=[C:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]([O:21]CC)=[O:20])=[O:12])[CH:8]=[CH:9][N:4]2[N:3]=1.O.[OH-].[Li+]>CO.O>[Br:1][C:2]1[N:24]=[C:5]2[CH:6]=[C:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]([OH:21])=[O:20])=[O:12])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of ethyl 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate (1.2 g, 3.05 mmol) and lithium hydroxide hydrate (512 mg, 12.2 mmol) in methanol (40 ml) and water (10 ml) was stirred for 4 hours at 50° C. The solvent was evaporated, the residue was dissolved with water and acidified to pH=0 using hydrochloric acid 37%. The precipitated solid was filtered off and washed with water and dried in vacuo affording 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (929 mg, 83.4%) as a light brown solid. mp: >250° C., MS: m/z=362.7/364.8 (M+H+)

Workup

customThe solvent was evaporated
dissolutionthe residue was dissolved with water
filtrationThe precipitated solid was filtered off
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-1d0c9e33e7964cbcbd7cedf8ba4ae117
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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