Methyl iodide → HCID 70665035, compound

HRID 1403559Notes

Reaction equation

HRID 1403559 reaction equation
[C:1]([NH:5][C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:29]I>O1CCCC1>[C:1]([N:5]([CH3:29])[C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70664982HCID 70664982, compound

Product 1

HCID 70665035HCID 70665035, compoundYield 7.13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(tert-butylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (115 mg, 0.33 mmol) in tetrahydrofuran (30 mL) was added sodium hydride (65 mg, 2.71 mmol) at 0° C. and then stirred for 10 minutes at room temperature. Methyliodide (185 mg, 1.30 mmol) was then added with stirring, and the reaction was allowed to proceed overnight at room temperature. The reaction was quenched with water (50 mL), adjusted to pH 5 with HCl (3N), extracted with ethyl acetate (3×80 mL) and the organic layers combined, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the residue. Purification via Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, water with 0.05% TFA and CH3CN (10% CH3CN up to 45% in 10 min); Detector, UV 220 nm] afforded 3-(tert-butyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a light yellow solid (8.20 mg, 7.13%).

Workup

  1. stirringwith stirring
  2. waitto proceed overnight at room temperature
  3. customThe reaction was quenched with water (50 mL)
  4. extractionextracted with ethyl acetate (3×80 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give the residue
  8. customPurification via Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC)
  9. waitmobile phase, water with 0.05% TFA and CH3CN (10% CH3CN up to 45% in 10 min)

Sources & evidence

ORD record
ord-cec6d5751bca4b8c8176e672795b1bf1
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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