Ethanol → 7-[(cyclopropylmethyl)(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)-1H-indole-2-carboxylic acid

HRID 504817Notes

Reaction equation

HRID 504817 reaction equation
[CH:1]1([CH2:4][N:5]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:27])=[O:26])[C:6]2[CH:7]=[C:8]([O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:9]=[C:10]3[C:14]=2[NH:13][C:12]([C:15]([O:17]CC)=[O:16])=[CH:11]3)[CH2:3][CH2:2]1.C(O)C.[OH-].[Na+]>O1CCCC1>[CH:1]1([CH2:4][N:5]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:27])=[O:26])[C:6]2[CH:7]=[C:8]([O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:9]=[C:10]3[C:14]=2[NH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11]3)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 57476246ethyl 7-[(cyclopropylmethyl)(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)-1H-indole-2-carboxylate

Product 1

HCID 574762477-[(cyclopropylmethyl)(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)-1H-indole-2-carboxylic acidYield 103%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of ethyl 7-[(cyclopropylmethyl)(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)-1H-indole-2-carboxylate (650 mg), ethanol (10 mL) and tetrahydrofuran (10 mL) was added 2N aqueous sodium hydroxide solution (3.43 mL) at room temperature, and the mixture was stirred at 50° C. for 5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and 1N aqueous hydrochloric acid. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered, and the filtrate was concentrated under reduced pressure to give the title compound (630 mg, yield 99%) as a colorless amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate and 1N aqueous hydrochloric acid
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2d09996dfa7e4f588141f587b003d7d6
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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