Sodium Hydroxide → HCID 52941025, compound

HRID 1510099Notes

Reaction equation

HRID 1510099 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:29]([N:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)=[O:30])=[C:10]([O:20][C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[CH3:28])[N:11]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CC(=O)OCC>[F:27][C:25]1[CH:24]=[CH:23][C:22]([CH3:28])=[C:21]([CH:26]=1)[O:20][C:10]1[N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:12]2[C:8]([C:9]=1[C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66920386HCID 66920386, compound

Product 1

HCID 52941025HCID 52941025, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

The compound of example 27, step 1 (18 mg, 30.6 μmol) was dissolved in MOH (1 ml), a 2 N sodium hydroxide solution (300 μl) was added, and the mixture was stirred at 40° C. for 3 h. The mixture was diluted with EA and washed with a saturated solution of ammonium chloride. The organic layer was dried over sodium sulfate and concentrated. The residue was dissolved in DCM (1 ml), TFA (0.3 ml) was added, and the mixture was stirred at room temperature for 1 h. The solvents were evaporated and the obtained solid residue was purified by preparative HPLC. The eluate was lyophilized overnight. The residue was dissolved in a small quantity of MOH, mixed with hydrochloric acid (0.1 M) and lyophilized overnight. 3.6 mg of the title compound were obtained in the form of the 2-(5-fluoro-2-methyl-phenoxy)-1-phenyl-3-(piperazine-1-carbonyl)-1H-indole-6-carboxylic acid hydrochloride.

Workup

  1. washwashed with a saturated solution of ammonium chloride
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in DCM (1 ml)
  5. additionTFA (0.3 ml) was added
  6. stirringthe mixture was stirred at room temperature for 1 h
  7. customThe solvents were evaporated
  8. customthe obtained solid residue was purified by preparative HPLC
  9. waitThe eluate was lyophilized overnight
  10. dissolutionThe residue was dissolved in a small quantity of MOH
  11. additionmixed with hydrochloric acid (0.1 M)
  12. waitlyophilized overnight

Sources & evidence

ORD record
ord-fcb900ff10a24123a5b3878a9b5b7b97
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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