Sodium Hydroxide → HCID 70664849, compound

HRID 1403369Notes

Reaction equation

HRID 1403369 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]([O:27]C)=[O:26])[CH:16]=4)[N:11]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]([OH:27])=[O:26])[CH:16]=4)[N:11]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70665061HCID 70665061, compound

Product 1

HCID 70664849HCID 70664849, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(1-benzofuran-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (105 mg, crude) in methanol (30 mL) was added sodium hydroxide (59.7 mg, 1.49 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), extracted with ethyl acetate (3×80 mL) and the organic layers combined, dried over anhydrous magnesium sulfate and concentrated under vacuum to give the residue, which was purified by Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, water with 0.05% NH3H2O and CH3CN (10% CH3CN up to 45% in 10 min); Detector, UV 220 nm] to afford 2-(1-benzofuran-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid as a yellow solid (26.3 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (30 mL)
  3. extractionextracted with ethyl acetate (3×80 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give the residue, which
  7. customwas purified by Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC)
  8. waitmobile phase, water with 0.05% NH3H2O and CH3CN (10% CH3CN up to 45% in 10 min)

Sources & evidence

ORD record
ord-0152a76d16e3499da9b3ff19f346e96b
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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