Water → HCID 70664829, compound

HRID 1403352Notes

Reaction equation

HRID 1403352 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]2[S:6][C:7]([C:9]3[C:18]([N:19]([CH:21]([CH3:23])[CH3:22])[CH3:20])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:24]([O:26]C)=[O:25])[CH:15]=4)[N:10]=3)=[CH:8][C:4]=2[CH:3]=1.[OH-].[Na+].O>O1CCCC1>[F:1][C:2]1[CH:29]=[CH:28][C:5]2[S:6][C:7]([C:9]3[C:18]([N:19]([CH:21]([CH3:22])[CH3:23])[CH3:20])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:24]([OH:26])=[O:25])[CH:15]=4)[N:10]=3)=[CH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 60171606HCID 60171606, compound

Product 1

HCID 70664829HCID 70664829, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(5-fluorobenzo[b]thiophen-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (148 mg, 0.36 mmol) in tetrahydrofuran (25 mL) was added sodium hydroxide (43.4 mg, 1.08 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 hydrochloric acid (3N). The solids were collected by filtration to afford 2-(5-fluorobenzo[b]thiophen-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid (69 mg, 49%).

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-8c12a65ac86e4fe88a823f105b21a9aa
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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