Sodium Hydroxide → HCID 59398388, compound

HRID 2193217Notes

Reaction equation

HRID 2193217 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:36])=[CH:8][C:9](=[O:35])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21][CH2:22][CH2:23][S:24][C:25]3[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=3[C:27]([O:29]C)=[O:28])[CH2:17][CH2:16]2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:36])=[CH:8][C:9](=[O:35])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([NH:21][CH2:22][CH2:23][S:24][C:25]3[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=3[C:27]([OH:29])=[O:28])[CH2:19][CH2:20]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59398419HCID 59398419, compound

Product 1

HCID 59398388HCID 59398388, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1 mL of an ethanol solution containing 60 mg of methyl 2-((2-(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-ylamino)ethyl)thio)benzoate, 0.1 mL of 20% aqueous sodium hydroxide solution was added at room temperature and stirred for 1 hour and 40 min. After the solvent was removed from the reaction mixture under reduced pressure, water was added, adjusted to pH 6.2 with 6.0 mol/L hydrochloric acid. The resulting solid was filtered, washed with water and diethylether to give 28 mg of 2-((2-(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-ylamino)ethyl)thio)benzoic acid as a white solid.

Workup

  1. additionwas added at room temperature
  2. customAfter the solvent was removed from the reaction mixture under reduced pressure, water
  3. additionwas added
  4. filtrationThe resulting solid was filtered
  5. washwashed with water and diethylether

Sources & evidence

ORD record
ord-c18b7ea1c67e4d25bc198fb0d38bd095
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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