Hydrochloric Acid → 3-(isopropyl(methyl)amino)-2-(1-methyl-1H-indazol-6-yl)quinoxaline-6-carboxylic acid

HRID 1403305Notes

Reaction equation

HRID 1403305 reaction equation
[CH:1]([N:4]([CH3:29])[C:5]1[C:6]([C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][N:25]3[CH3:28])=[CH:21][CH:20]=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].O[Li].O.Cl>O1CCCC1.O>[CH:1]([N:4]([CH3:29])[C:5]1[C:6]([C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][N:25]3[CH3:28])=[CH:21][CH:20]=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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 70664942methyl 3-(isopropyl(methyl)amino)-2-(1-methyl-1H-indazol-6-yl)quinoxaline-6-carboxylate

Product 1

HCID 670419473-(isopropyl(methyl)amino)-2-(1-methyl-1H-indazol-6-yl)quinoxaline-6-carboxylic acidYield 30.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(isopropyl(methyl)amino)-2-(1-methyl-1H-indazol-6-yl)quinoxaline-6-carboxylate (70 mg, 0.18 mmol) in tetrahydrofuran (20 mL) was added LiOH.H2O (9.0 mg, 0.36 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 (30 mL), adjusted the pH to 6 with hydrochloric acid (3N), and filtered to give 3-(isopropyl(methyl)amino)-2-(1-methyl-1H-indazol-6-yl)quinoxaline-6-carboxylic acid as a light yellow solid (20.5 mg, 30%).

Workup

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

Sources & evidence

ORD record
ord-a5719ed95a5b476eba0ea4987be1b270
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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