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

HRID 1802206Notes

Reaction equation

[CH3:1][N:2]([CH3:26])[C:3]1[N:25]=[C:6]2[CH:7]=[C:8]([NH:11][C:12]([C:14]3[N:18]([CH3:19])[N:17]=[CH:16][C:15]=3[C:20]([O:22]CC)=[O:21])=[O:13])[CH:9]=[CH:10][N:5]2[N:4]=1.O.[OH-].[Li+]>CO.O>[CH3:1][N:2]([CH3:26])[C:3]1[N:25]=[C:6]2[CH:7]=[C:8]([NH:11][C:12]([C:14]3[N:18]([CH3:19])[N:17]=[CH:16][C:15]=3[C:20]([OH:22])=[O:21])=[O:13])[CH:9]=[CH:10][N:5]2[N:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of ethyl 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate (1.24 g, 3.47 mmol) and lithium hydroxide monohydrate (291 mg, 6.94 mmol) in methanol (20 ml) and water (5 ml) is stirred for 4 hours at 50° C. The solvent is evaporated. The brown oily residue is dissolved in water and acidified to pH=5 with 2N aqueous hydrochloric acid (3.47 ml). The precipitated off-white solid is collected by filtration, dissolved in methanol and evaporated affording 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (1.09 g, 95.3%) as an off-white solid. Mp.: >250° C. MS: m/z=328.0 (M−H+).

Workup

customThe solvent is evaporated
dissolutionThe brown oily residue is dissolved in water
filtrationThe precipitated off-white solid is collected by filtration
dissolutiondissolved in methanol
customevaporated

Sources & evidence

ORD record: ord-0007ee1978fd45f098a6f9d709a8f9f7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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