Hydrochloric Acid → HCID 68621686, compound

HRID 407158Notes

Reaction equation

HRID 407158 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([C:24]([O:26]CC)=[O:25])=[N:20][NH:21]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:7].[OH-].[Na+].Cl>C1COCC1.O.CO>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([C:24]([OH:26])=[O:25])=[N:20][NH:21]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 46234711HCID 46234711, compound

Product 1

HCID 68621686HCID 68621686, compoundYield 127%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of ethyl 6-(4-(3-(trifluoromethyl)benzamido)phenyl)-1H-indazole-3-carboxylate (12 mg, 25 μmol) in THF/water/methanol (10/1/1, 2.5 Ml), was added 1N aqueous sodium hydroxide solution (1.3 Ml). The mixture was stirred at 70° C. for 12 h and cooled to room temperature. The pH of solution was adjusted to 4-5 with 1N hydrochloric acid aqueous solution. The aqueous solution was extracted with ethyl acetate and the combined organic layer was washed with water, dried over magnesium sulfated, and concentrated under reduced pressure to give 6-(4-(3-(trifluoromethyl)benzamido)phenyl)-1H-indazole-3-carboxylic acid (13.5 mg), which was used in next step without purification.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washthe combined organic layer was washed with water
  4. dry with materialdried over magnesium
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97b9b329e12045c1916d90e27a1d5b3a
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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