Hydrochloric Acid → HCID 58138849, compound

HRID 1677714Notes

Reaction equation

HRID 1677714 reaction equation
C([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:8]([C:22](=[O:36])[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([S:31](=[O:35])(=[O:34])[NH:32][CH3:33])=[CH:27][CH:26]=2)[CH:7]=1)=[O:5])C.[OH-].[K+].Cl>O.CCO.C(OCC)(=O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[C:13]3[C:9](=[C:8]([C:22](=[O:36])[NH:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([S:31](=[O:34])(=[O:35])[NH:32][CH3:33])=[CH:27][CH:26]=4)[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:14]=3)[CH:10]=[N:11]2)=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58138783HCID 58138783, compound

Product 1

HCID 58138849HCID 58138849, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-(4-fluoro-phenyl)-4-(4-methylsulfamoyl-benzylcarbamoyl)-1H-indazole-6-carboxylic acid ethyl ester (0.13 g, 0.26 mmol) in H2O (10 mL) and EtOH (20 mL) was added a 2 N solution of aqueous KOH (10 mL, 20 mmol). The mixture was warmed at reflux for 1 hour and cooled to room temperature. The mixture was acidified with 2 N aqueous HCl (pH=3-4) and diluted with ethyl acetate (30 mL). The organic layer was separated and washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated. The residue was triturated with diethyl ether (10 mL) to afford the title compound.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureat reflux for 1 hour
  3. customThe organic layer was separated
  4. washwashed with brine (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with diethyl ether (10 mL)

Sources & evidence

ORD record
ord-4c583da9abde4d8584e04cff62ddcaaa
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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