Ethanamine, 2,2,2-trifluoro- → HCID 70664799, compound

HRID 1403607Notes

Reaction equation

HRID 1403607 reaction equation
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[F:23][C:24]([F:28])([F:27])[CH2:25][NH2:26].CCN(C(C)C)C(C)C>CS(C)=O.O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:2]([NH:26][CH2:25][C:24]([F:28])([F:27])[F:23])=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 81531DiisopropylethylamineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 70664799HCID 70664799, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (500 mg, 1.58 mmol) in DMSO (23 ml) was added 2,2,2-trifluoroethan-1-amine (188 mg, 1.90 mmol) and DIEA (407 mg, 3.15 mmol,) with stirring, and the resulting mixture was allowed to react for 4 days at 110° C. in an oil bath. The reaction mixture was diluted with water (80 ml), extracted with dichloromethane (4×15 ml), dried over anhydrous sodium sulfate, and concentrated in vacuo to give the residue, which was purified via silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford methyl 2-(4-fluorophenyl)-3-[(2,2,2-trifluoroethyl)amino]quinoxaline-6-carboxylate as a yellow solid (400 mg, 67%).

Workup

  1. customto react for 4 days at 110° C. in an oil bath
  2. extractionextracted with dichloromethane (4×15 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the residue, which
  6. customwas purified via silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-3dc744ea2df14aa888172d99bf14944d
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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