Methyl iodide → HCID 70665039, compound

HRID 1403550Notes

Reaction equation

HRID 1403550 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:16]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[N:17][C:18]3[C:23]([N:24]=2)=[CH:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][CH:19]=3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:39]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH3:39])[C:15]2[C:16]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)=[N:17][C:18]3[C:23]([N:24]=2)=[CH:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][CH:19]=3)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70665004HCID 70665004, compound

Product 1

HCID 70665039HCID 70665039, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200.0 mg, 0.42 mmol) in tetrahydrofuran (10 mL) was added sodium hydride (50.0 mg, 2.08 mmol) at 0° C. and stirred for 30 minutes at room temperature. Subsequently, iodomethane (350.0 mg, 2.47 mmol) was added and stirred overnight at room temperature. The reaction mixture was then quenched by the addition of NH4Cl solution (100 mL), extracted with dichloromethane (3×15 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to afford methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-yl)(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (210 mg, crude).

Workup

  1. stirringstirred overnight at room temperature
  2. customThe reaction mixture was then quenched by the addition of NH4Cl solution (100 mL)
  3. extractionextracted with dichloromethane (3×15 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62debc94be644e439ec9bccd0467f8ab
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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