Methyl iodide → 3-(Cyclopropyl(methyl)amino)-2-phenylquinoxaline-6-carboxylic acid

HRID 1405528Notes

Reaction equation

HRID 1405528 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=3)[CH2:3][CH2:2]1.[H-].[Na+].[CH3:27]I>O1CCCC1>[CH:1]1([N:4]([CH3:27])[C:5]2[C:6]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=3)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67042136Methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 509910233-(Cyclopropyl(methyl)amino)-2-phenylquinoxaline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate (182.4 mg, 0.56 mmol, 1.00 equiv, 98%) in tetrahydrofuran (17 mL). Sodium hydride (274.5 mg, 11.44 mmol, 20.00 equiv) was added. The resulting solution was stirred for 1 h at room temperature. This was followed by the dropwise addition of CH3I (809.4 mg, 5.70 mmol, 10.00 equiv) with stirring at 0° C. The resulting solution was allowed to react, with stirring, overnight at room temperature. The resulting mixture was concentrated under vacuum and diluted with 10 ml of water. The pH value of the aqueous solution was adjusted to 3-4 with 1N hydrogen chloride. The resulting solid was collected by filtration and washed with water and methanol. This resulted in 66.5 mg (36%) of 3-(cyclopropyl(methyl)amino)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringwith stirring at 0° C
  4. customto react
  5. stirringwith stirring, overnight at room temperature
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. additiondiluted with 10 ml of water
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with water and methanol
  10. customThis resulted in 66.5 mg (36%) of 3-(cyclopropyl(methyl)amino)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-664ce7cbb7be410e9476d9250e92c1ff
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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