Water → HCID 50991662, compound

HRID 1403320Notes

Reaction equation

HRID 1403320 reaction equation
[CH:1]([N:4]([CH3:30])[C:5]1[C:6]([C:19]2[CH:20]=[N:21][C:22]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:23][CH:24]=2)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[CH:1]([N:4]([CH3:30])[C:5]1[C:6]([C:19]2[CH:20]=[N:21][C:22]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:23][CH:24]=2)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70665111HCID 70665111, compound

Product 1

HCID 50991662HCID 50991662, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(isopropyl(methyl)amino)-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)quinoxaline-6-carboxylate (130.0 mg, 0.32 mmol) in methanol (20 mL) was added sodium hydroxide (64.3 mg, 1.61 mmol) and water (1 mL) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (20 mL) and adjusted to pH 7 with hydrochloric acid (1N). The solids were collected to afford 3-(isopropyl(methyl)amino)-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)quinoxaline-6-carboxylic acid as a light yellow solid (60.3 mg, 48%).

Workup

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

Sources & evidence

ORD record
ord-1a5dafd14f9f49f0b9b70e74a0d5569d
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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