Methanol → 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid

HRID 1802264Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:31])[C:10]=1[C:11](=[O:30])[NH:12][C:13]1[CH:18]=[CH:17][N:16]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[N:21]=[C:15]2[CH:14]=1)=[O:5])C.CO.O.[Li+].[OH-]>C1COCC1>[CH3:29][O:28][C:24]1[CH:23]=[C:22]([C:20]2[N:21]=[C:15]3[CH:14]=[C:13]([NH:12][C:11]([C:10]4[N:9]([CH3:31])[N:8]=[CH:7][C:6]=4[C:4]([OH:5])=[O:3])=[O:30])[CH:18]=[CH:17][N:16]3[N:19]=2)[CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (3.5 g, 8.33 mmol) in a mixture of THF (20 ml), MeOH (14 ml) and water (7 ml) was added LiOH×H2O (1.0 g, 25.0 mmol) at 0° C. The reaction mixture was stirred at 25° C. for 4 h. Solvents were removed in vacuum and the resultant crude material was diluted with water (150 ml). The aqueous layer was washed with ether (2×100 ml), cooled to 0° C., and slowly acidified (pH 5) with aqueous 1N HCl solution under stirring. The resultant precipitated solid was filtered and dried under vacuum to give 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid as white solid (5.9 g; crude, quant). LC-MS: m/z=393.0 [M+H]+.

Workup

customSolvents were removed in vacuum
additionthe resultant crude material was diluted with water (150 ml)
washThe aqueous layer was washed with ether (2×100 ml)
temperaturecooled to 0° C.
stirringunder stirring
customThe resultant precipitated solid
filtrationwas filtered
customdried under vacuum

Sources & evidence

ORD record: ord-58abc3d56dc843409b7d922bbcb1f69f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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