Methyl iodide → HCID 67041674, compound

HRID 1403554Notes

Reaction equation

HRID 1403554 reaction equation
[C@@H: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)([CH2:3][CH3:4])[CH3:2].[H-].[Na+].I[CH3:30]>O1CCCC1>[C@@H:1]([N:5]([CH3:30])[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)([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70665065HCID 70665065, compound

Product 1

HCID 67041674HCID 67041674, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 3-(sec-butylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (280.0 mg, 0.79 mmol) in tetrahydrofuran (30 mL) was added sodium hydride (127 mg, 3.17 mmol) and stirred for 1 h at room temperature. Subsequently, iodomethane (570 mg, 3.97 mmol) was added and stirred overnight at room temperature. The reaction was concentrated in vacuo and then quenched by the addition of water (20 mL), adjusted to pH 5 with hydrochloric acid (1N). The solids were collected by filtration to afford (S)-3-(sec-butyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a yellow solid (124.3 mg, 44%).

Workup

  1. stirringstirred overnight at room temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. customquenched by the addition of water (20 mL)
  4. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-8ecc794a25e14dcc9f34be77e1992683
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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