Sodium Hydroxide → HCID 67440389, compound

HRID 1801386Notes

Reaction equation

HRID 1801386 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14]C)=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:31])(=[O:30])[NH:23][CH:24]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25]2)[CH:17]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:1][C:2]1([CH3:32])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:31])(=[O:30])[NH:23][CH:24]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25]2)[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67443241HCID 67443241, compound

Product 1

HCID 67440389HCID 67440389, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3,3-dimethyl-2-(3-(N-(1-methylpyrrolidin-3-yl)sulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (140 mg, 0.31 mmol) in methanol/tetrahydrofuran (5 mL/5 mL) was added 1N sodium hydroxide (4.59 mL). The resultant mixture was heated to reflux for 2.5 h. Organic solvent was removed and the residue was dissolved in water. The aqueous layer was acidified to pH=4. The precipitates were filtered, and dissolved in tetrahydrofuran, dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed, and after evaporation, the residue was treated with ethyl acetate to afford 40 mg of 3,3-dimethyl-2-(3-(N-(1-methylpyrrolidin-3-yl)sulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid. (Yield: 29%). MS (ESI+APCI) M+1=444.2.

Workup

  1. temperatureto reflux for 2.5 h
  2. customOrganic solvent was removed
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe precipitates were filtered
  5. dissolutiondissolved in tetrahydrofuran
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAnhydrous magnesium sulfate was removed
  8. customafter evaporation
  9. additionthe residue was treated with ethyl acetate

Sources & evidence

ORD record
ord-63ef9bf2a696488189e3d18a3326e275
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…