Methyl iodide → HCID 70664846, compound

HRID 1403561Notes

Reaction equation

HRID 1403561 reaction equation
[CH:1]1([NH:7][C:8]2[C:9]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][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)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:31]I>O1CCCC1>[CH:1]1([N:7]([CH3:31])[C:8]2[C:9]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][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)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70665078HCID 70665078, compound

Product 1

HCID 70664846HCID 70664846, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(cyclohexylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200 mg, 0.53 mmol) in tetrahydrofuran (30 mL) was added sodium hydride (105.5 mg, 4.40 mmol) and CH3I (299.9 mg, 2.11 mmol), and the reaction was allowed to proceed with stirring overnight at room temperature. The reaction was then quenched by the addition of water (50 mL), adjusted pH to 5 with HCl (3N). The resulting solution was extracted with ethyl acetate (3×80 mL) and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the crude product. The crude product was re-crystallized from ethyl acetate:petroleum ether (1:5) to afford 3-(cyclohexyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid (100 mg, 48%) as a light yellow solid.

Workup

  1. customThe reaction was then quenched by the addition of water (50 mL)
  2. extractionThe resulting solution was extracted with ethyl acetate (3×80 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe crude product was re-crystallized from ethyl acetate:petroleum ether (1:5)

Sources & evidence

ORD record
ord-91400df59a0e4c219e2293ffdec2b315
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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