Hydrochloric Acid → 4-(2,4-Difluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

HRID 2282248Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:18]2[C:19]([CH3:27])=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)[S:12][C:13]=1[C:14]([O:16]C)=[O:15].[OH-].[Na+].CCOC(C)=O.Cl>C1COCC1.CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:18]2[C:19]([CH3:27])=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)[S:12][C:13]=1[C:14]([OH:16])=[O:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of methyl 4-(2,4-difluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate (250 mg, 0.649 mmol) obtained above in THF (5 mL) and MeOH (5 mL), was added 2N aqueous solution of sodium hydroxide (1 mL) and the mixture was stirred for 2 h at 60° C. To the mixture, was added a 2:1 mixture of EtOAc and THF (60 mL) and 1N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with a 2:1 mixture of EtOAc and THF (10 mL). The combined organic layers were washed with brine (5 mL) and then dried over anhydrous sodium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain title compound (225 mg, 93%) as a pale yellow solid.

Workup

additionTo the mixture, was added
customThe organic layer was separated
extractionthe aqueous layer was extracted with a 2:1 mixture of EtOAc and THF (10 mL)
washThe combined organic layers were washed with brine (5 mL)
dry with materialdried over anhydrous sodium sulfate
customInsoluble materials were removed by filtration
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-ab43d2760e314fe7973d2d6d47a0038c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139589B2

Reaction notes

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