Water → HCID 70664763, compound

HRID 1403358Notes

Reaction equation

HRID 1403358 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:21]([N:22]([CH:24]([CH3:26])[CH3:25])[CH3:23])=[N:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:27]([O:29]C)=[O:28])[CH:18]=4)[N:13]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4]1)[CH3:2].[OH-].[Na+].O>O1CCCC1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:21]([N:22]([CH:24]([CH3:25])[CH3:26])[CH3:23])=[N:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:27]([OH:29])=[O:28])[CH:18]=4)[N:13]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70664635HCID 70664635, compound

Product 1

HCID 70664763HCID 70664763, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(1-ethyl-1H-indazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (80 mg, 0.20 mmol) in tetrahydrofuran (25 mL) was added sodium hydroxide (34 mg, 0.85 mmol) and water (2 mL) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (20 mL) and adjusted to pH 5 with HCl (3N). The solids were collected by filtration to afford 2-(1-ethyl-1H-indazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as yellow solid (18.6 mg, 24%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (20 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-cc1131052ff84459b3f902f911f6c431
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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