Methyl iodide → HCID 70664881, compound

HRID 1403648Notes

Reaction equation

HRID 1403648 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([NH:18][C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:27]([O:29]C)=[O:28])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:33]I>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH3:33])[C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:27]([OH:29])=[O:28])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70664987HCID 70664987, compound

Product 1

HCID 70664881HCID 70664881, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-(4-fluorophenyl)-3-(1-phenylethylamino)quinoxaline-6-carboxylate (100 mg, 0.25 mmol) in tetrahydrofuran (15 mL) was added sodium hydride (30 mg, 0.75 mmol), and the reaction mixture was stirred for 10 minutes. CH3I (106 mg, 0.75 mmol) was added, and the resulting mixture was stirred overnight. The reaction was then quenched by the addition of NH4Cl solution (50 mL) and adjusted pH to 5 with hydrochloric acid (3N). The solids were collected by filtration to afford (S)-2-(4-fluorophenyl)-3-(methyl(1-phenylethyl)amino)quinoxaline-6-carboxylic acid as a yellow solid (47.5 mg, 48%).

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. customThe reaction was then quenched by the addition of NH4Cl solution (50 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-27277a9b3ae946e28ba7bf2def2e0cd1
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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