Sodium Hydroxide → 3-[Methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylic acid

HRID 1403485Notes

Reaction equation

HRID 1403485 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]3[C:22]([N:23]([CH3:27])[CH:24]([CH3:26])[CH3:25])=[N:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:28]([O:30]C)=[O:29])[CH:19]=4)[N:14]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[CH3:27][N:23]([CH:24]([CH3:26])[CH3:25])[C:22]1[C:13]([C:11]2[O:12][C:8]([C:5]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)=[N:14][C:15]2[C:20]([N:21]=1)=[CH:19][C:18]([C:28]([OH:30])=[O:29])=[CH:17][CH:16]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70665195Methyl 2-[5-(4-fluorophenyl)furan-2-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate

Product 1

HCID 601985343-[Methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylic acidYield 19.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-[5-(4-fluorophenyl)furan-2-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (110 mg, 0.26 mmol) in methanol (30 mL) and water (2 mL) was added sodium hydroxide (42 mg, 1.05 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 HCl (3N). The solids were collected by filtration to afford 3-[methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylic acid as a light yellow solid (19.3 mg, 18%).

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-cba368d468054d9abc3412dafeea0e53
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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