Hydrochloric Acid → HCID 70665011, compound

HRID 1403566Notes

Reaction equation

HRID 1403566 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:22]([O:24]C)=[O:23])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:29][CH3:30].Cl>O1CCCC1.O>[CH2:29]([N:18]([CH:19]([CH3:21])[CH3:20])[C:17]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:22]([OH:24])=[O:23])=[CH:12][CH:11]=2)[CH3:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70665294HCID 70665294, compound

Product 1

HCID 70665011HCID 70665011, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-(isopropylamino)quinoxaline-6-carboxylate (95 mg, 0.28 mmol) in tetrahydrofuran (20 mL) was added sodium hydride (23 mg, 0.96 mmol) and stirred for 10 minutes. Subsequently, iodoethane (43.7 mg, 0.28 mmol) was added and stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure to afford a residue, which was dissolved in water (25 mL) and the pH adjusted to 6 with hydrochloric acid (3N). The product precipitated and was filtered to afford 3-(ethyl(isopropyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a light yellow solid (28.4 mg, 29%).

Workup

  1. stirringstirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford a residue, which
  4. customThe product precipitated
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-415cc9a9db254c6fbe40a26ef2ff5193
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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