Water → 7-(Cyclopentylamino)-2-phenyl-1H-indole-5-carboxylic acid

HRID 1466500Notes

Reaction equation

HRID 1466500 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([NH:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:14]=1)[NH:11][C:10]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:9]2)=[O:5])C.O.[OH-].[Na+]>CO>[CH:16]1([NH:15][C:13]2[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[C:8]3[C:12]=2[NH:11][C:10]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:9]3)[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 252139517-(Cyclopentyl)amino-2-phenyl-1H-indole-5-carboxylic acid ethyl ester

Product 1

HCID 252141807-(Cyclopentylamino)-2-phenyl-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

7-(Cyclopentyl)amino-2-phenyl-1H-indole-5-carboxylic acid ethyl ester (5 g, 14.3 mmol) prepared in Example 28 was added to a solvent mixture of MeOH (20 mL) and water (20 mL). NaOH (1.3 g, 33.8 mmol) was added thereto, and the mixture was stirred for 4 h at room temperature. After completion of the reaction, MeOH was removed under reduced pressure, and 1N HCl was added to the residue. The resulting mixture was extracted with EtOAc, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was recrystallized from EtOAc and n-Hex to give the title compound.

Workup

  1. customwas removed under reduced pressure, and 1N HCl
  2. additionwas added to the residue
  3. extractionThe resulting mixture was extracted with EtOAc
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was recrystallized from EtOAc and n-Hex

Sources & evidence

ORD record
ord-9cd329266d954f9b82459e89719cd4b9
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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