Sodium Hydroxide → HCID 70665028, compound

HRID 1403410Notes

Reaction equation

HRID 1403410 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]([C:9]3[C:18]([N:19]4[CH2:23][CH2:22][CH2:21][C@@H:20]4[CH3:24])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:25]([O:27]C)=[O:26])[CH:15]=4)[N:10]=3)=[CH:8][C:4]=2[CH:3]=1.[OH-].[Na+]>CO.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]([C:9]3[C:18]([N:19]4[CH2:23][CH2:22][CH2:21][C@@H:20]4[CH3:24])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:25]([OH:27])=[O:26])[CH:15]=4)[N:10]=3)=[CH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70665050HCID 70665050, compound

Product 1

HCID 70665028HCID 70665028, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of (S)-methyl 2-(5-fluorobenzo[b]thiophen-2-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (89 mg, 0.21 mmol) in methanol (25 mL) and chloroform (5 mL) was added sodium hydroxide (25.2 mg, 0.63 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (15 mL), adjusted pH to 5 with HCl (3 N) to give the precipitate, which was collected by filtration to afford (S)-2-(5-fluorobenzo[b]thiophen-2-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid (56 mg, 65%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (15 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5a8c786c446947cd9b0e2e41a2a996de
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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