Hydrogen Peroxide → HCID 57520188, compound

HRID 1520155Notes

Reaction equation

HRID 1520155 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[C:14]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:15][C:16]3[C:21]([N:22]=1)=[CH:20][C:19]([C:23]([O:25]C)=[O:24])=[CH:18][CH:17]=3)[CH2:8][CH2:7][CH2:6]2)#[N:2].[OH:34]O.[OH-].[Na+]>CS(C)=O.CCO>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[C:14]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:15][C:16]3[C:21]([N:22]=1)=[CH:20][C:19]([C:23]([OH:25])=[O:24])=[CH:18][CH:17]=3)[CH2:8][CH2:7][CH2:6]2)(=[O:34])[NH2:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 68194321HCID 68194321, compound

Product 1

HCID 57520188HCID 57520188, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

To a solution of methyl 3-(6-cyano-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (150 mg, 0.34 mmol) in DMSO (1.6 mL) and EtOH (6.4 mL) was added H2O2 (1.2 mL, 40%), NaOH (0.4 mL, 1M) with stirring overnight at room temperature. The resulting mixture was concentrated under vacuum, diluted with water (15 mL), adjusted pH to 7 with AcOH. The solids were collected by filtration to give 3-(6-carbamoyl-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a solid (131 mg, 87%).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additiondiluted with water (15 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-80cc1e761b7a44978d5b55ddc54108cf
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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