Methyl iodide → (S)-3-(sec-butyl(methyl)amino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid

HRID 1403440Notes

Reaction equation

HRID 1403440 reaction equation
[C@@H:1]([NH:5][C:6]1[C:7]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=3[CH:24]=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+].[CH3:32]I>C1COCC1>[C@@H:1]([N:5]([CH3:32])[C:6]1[C:7]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=3[CH:24]=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 70665045(S)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate

Product 1

HCID 70664925(S)-3-(sec-butyl(methyl)amino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acidYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate (130 mg, 0.33 mmol) in THF (20 mL) was added NaH (52 mg, 1.32 mmol) and CH3I (188 mg, 1.32 mmol). The resulting solution was stirred overnight at room temperature and then the reaction mixture was poured into water/ice solution (20 mL). The mixture was evaporated until about 10 mL of water remained and adjusted to pH 5 with hydrochloric acid (1N). The product was collected by filtration to afford (S)-3-(sec-butyl(methyl)amino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid as a yellow solid (34.4 mg, 27%).

Workup

  1. customThe mixture was evaporated until about 10 mL of water
  2. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-2082e78426504d5db85602406d011a11
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…