Sodium Hydroxide → HCID 57520191, compound

HRID 1520160Notes

Reaction equation

HRID 1520160 reaction equation
[CH3:1][N:2]([CH3:37])[S:3]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[C:17]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[N:18][C:19]3[C:24]([N:25]=1)=[CH:23][C:22]([C:26]([O:28]C)=[O:27])=[CH:21][CH:20]=3)[CH2:11][CH2:10][CH2:9]2)(=[O:5])=[O:4].[OH-].[Na+]>CO.O>[CH3:1][N:2]([CH3:37])[S:3]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[C:17]([C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[N:18][C:19]3[C:24]([N:25]=1)=[CH:23][C:22]([C:26]([OH:28])=[O:27])=[CH:21][CH:20]=3)[CH2:11][CH2:10][CH2:9]2)(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 60171602HCID 60171602, compound

Product 1

HCID 57520191HCID 57520191, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-[6-(dimethylsulfamoyl)-1,2,3,4-tetrahydroquinolin-1-yl]-2-(4-fluorophenyl)quinoxaline-6-carboxylate (120 mg, 0.23 mmol) in methanol (30 mL) and water (2 mL) was added sodium hydroxide (36.9 mg, 0.92 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (30 mL) and adjusted to pH 5 with hydrogen chloride (3 N). The solids were collected by filtration to afford 3-[6-(dimethylsulfamoyl)-1,2,3,4-tetrahydroquinolin-1-yl]-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a light yellow solid (43.5 mg, 37%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (30 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-270081c5a5e247be97a90c6907001916
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

Loading…