Hydrochloric Acid → 3-Benzo[b]thiophen-2-yl-4-fluoro-1H-5-indazolecarboxylic Acid

HRID 503186Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]([F:23])=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[C:14]1[S:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH:15]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1.CO>[S:18]1[C:14]([C:8]2[C:7]3[C:11](=[CH:12][CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]=3[F:23])[NH:10][N:9]=2)=[CH:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]1=2

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 152 mg of 3-benzo[b]thiophen-2-yl-4-fluoro-1H-5-indazolecarboxylic acid methyl ester obtained in Production Example II-13-f in a mixture of 2 ml of tetrahydrofuran and 2 ml of methanol was added 1 ml of 5 N aqueous sodium hydroxide solution, and the mixture was stirred at 55° C. for 2.5 hours. After standing to cool, 5.5 ml of 1 N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was recrystallized from tetrahydrofuran-ethyl acetate, to give 104 mg of the title compound as pale red crystals.

Workup

temperatureto cool
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was sequentially washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe crude product was recrystallized from tetrahydrofuran-ethyl acetate

Sources & evidence

ORD record: ord-a3092f06379c4640ae9b8860fda2f410
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776890B2

Reaction notes

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