Hydrochloric Acid → 3-(Azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylic acid

HRID 1403408Notes

Reaction equation

HRID 1403408 reaction equation
[N:1]1([C:8]2[C:9]([C:22]3[S:26][C:25]4[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=4[CH:23]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO.O>[N:1]1([C:8]2[C:9]([C:22]3[S:26][C:25]4[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=4[CH:23]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70664777Methyl 3-(azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylate

Product 1

HCID 706648403-(Azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylic acidYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 3-(azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylate (82 mg, 0.2 mmol) in methanol (15 mL) was added sodium hydroxide (80 mg, 2 mmol) and water (1 mL). After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure to afford a residue, which was dissolved in water (10 mL), adjusted the pH value to 6 with HCl (3 N) and filtered to give 3-(azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylic acid as a light yellow solid (70.1 mg, 88%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto afford a residue, which
  3. filtrationfiltered

Sources & evidence

ORD record
ord-911cec86558f4d789ae2d76af211b628
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…