Hydrochloric Acid → 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

HRID 1802141Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([CH3:28])[C:9]=1[C:10](=[O:27])[NH:11][C:12]1[CH:17]=[CH:16][N:15]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:20]=[C:14]2[CH:13]=1)=[O:4].O.[OH-].[Li+].Cl>CO.O>[CH3:28][N:8]1[C:9]([C:10](=[O:27])[NH:11][C:12]2[CH:17]=[CH:16][N:15]3[N:18]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:20]=[C:14]3[CH:13]=2)=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[N:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

A white suspension of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid methyl ester (2.37 g, 6.3 mmol) and lithium hydroxide monohydrate (291 mg, 6.93 mmol) in methanol (100 ml) and water (20 ml) is stirred for 5/4 hr at 70° C. giving after 20 min a colorless solution. The methanol is removed in vacuo, the residue is diluted with water and the cooled aqueous solution is neutralized with 2N aqueous hydrochloric acid (3.46 ml, 6.03 mmol). The solid is collected by filtration and dried affording 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (2.21 g, 97%) as a white solid. mp.: >300° C. MS: m/z=361.1 (M+H+).

Workup

customgiving after 20 min a colorless solution
customThe methanol is removed in vacuo
additionthe residue is diluted with water
filtrationThe solid is collected by filtration
customdried

Sources & evidence

ORD record: ord-02716550a26b49c8896b34326df1f6c9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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