Sodium Hydroxide → [2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid

HRID 1678619Notes

Reaction equation

HRID 1678619 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([C:12]1[N:13]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:14]=[C:15]2[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]2)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[OH-].[Na+]>CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([N:13]2[C:12]([CH:5]([CH:6]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)[C:4]([OH:28])=[O:3])=[C:20]3[C:15]([CH:16]=[CH:17][CH:18]=[CH:19]3)=[N:14]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67131064[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl ester

Product 1

HCID 67131005[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acidYield 117.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl ester (9 mg, 23 μmol) in MeOH (0.5 ml) and 4 N aqueous NaOH (90 μl, 345 μmol) was heated for 14 h under reflux conditions. The solvent was removed under reduced pressure, ice water/1 N aqueous NaOH solution/TBME 1/1/2 was added and the layers were separated. The aqueous layer was extracted one more time with TBME. The aqueous layer was acidified with 1 N aqueous HCl solution and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the title compound (10 mg; quant.) as off-white solid which was sufficiently pure to be used in the next step. MS: m/e=369.1 [M+H+].

Workup

  1. customThe solvent was removed under reduced pressure, ice water/1 N aqueous NaOH solution/TBME 1/1/2
  2. additionwas added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted one more time with TBME
  5. extractionextracted two times with iPrOAc
  6. washThe combined extracts were washed with ice water/brine 1/1
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration the solvent
  9. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-d4b82aa0e86a45d293a85782a5ae93b0
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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