Hydrochloric Acid → HCID 50991661, compound

HRID 1403322Notes

Reaction equation

HRID 1403322 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([O:25]C)=[O:24])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.O[Li].O.Cl>O1CCCC1.O>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([OH:25])=[O:24])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 70664950HCID 70664950, compound

Product 1

HCID 50991661HCID 50991661, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(6-fluoropyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (130 mg, 0.37 mmol) in tetrahydrofuran (10 mL) was added LiOH.H2O (35 mg, 0.83 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 hydrochloric acid (1N). The solid was precipitated and filtered to afford 2-(6-fluoropyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (81.6 mg, 65%).

Workup

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

Sources & evidence

ORD record
ord-bfa3607ea19e48158fc355406aa1bf83
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…