Hydrochloric Acid → HCID 70665087, compound

HRID 1403652Notes

Reaction equation

HRID 1403652 reaction equation
[N:1]1([C:5]2[C:6]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=3)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO.O>[N:1]1([C:5]2[C:6]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=3)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70665190HCID 70665190, compound

Product 1

HCID 70665087HCID 70665087, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 3-(azetidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (60 mg, 0.18 mmol) in methanol (20 mL) was added sodium hydroxide (50 mg, 1.25 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 to pH 6 with hydrochloric acid (3N), and the product was precipitated and filtered to give 3-(azetidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a light yellow solid (35.3 mg, 61%).

Workup

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

Sources & evidence

ORD record
ord-1429d91815544906860a856eaf757ff4
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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