Hydrochloric Acid → HCID 70664896, compound

HRID 1403608Notes

Reaction equation

HRID 1403608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([NH:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]([O:26]C)=[O:25])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:31].Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([N:18]([CH3:31])[CH2:19][C:20]([F:21])([F:23])[F:22])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]([OH:26])=[O:25])[CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70664799HCID 70664799, compound

Product 1

HCID 70664896HCID 70664896, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-[(2,2,2-trifluoroethyl)amino]quinoxaline-6-carboxylate (400 mg, 1.05 mmol) in tetrahydrofuran (30 ml) was added sodium hydride (101 mg, 4.21 mmol) at 0° C. with stirring for 40 minutes and then iodomethane (899 mg, 6.33 mmol) was added to the reaction mixture, and the resulting mixture was allowed to react with stirring overnight at room temperature. The reaction mixture was adjusted pH to 4 with HCl to give the solid, which was collected by filtration to afford 2-(4-fluorophenyl)-3-[methyl(2,2,2-trifluoroethyl)amino]quinoxaline-6-carboxylic acid as a yellow solid (80.6 mg, 20%).

Workup

  1. customto react
  2. stirringwith stirring overnight at room temperature
  3. customto give the solid, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-08cf1e8aef814156a22ac1928e8674f6
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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