Trifluoroacetic acid → HCID 58575159, compound

HRID 1189471Notes

Reaction equation

HRID 1189471 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][CH2:18][C:19]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:16])[CH:6]=2.FC(F)(F)C(OC(=O)C(F)(F)F)=O.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]2[N:4]([C:19]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:18][N:17]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:16])[CH:6]=2

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 86660665HCID 86660665, compound

Product 1

HCID 58575159HCID 58575159, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed liquid of 520 mg of methyl 3-chloro-2-[(2-cyclopentyl-2-oxoethyl)amino]-7-methylquinoxaline-6-carboxylate and 11.3 mL of chloroform were added 4.00 mL of trifluoroacetic anhydride and 0.11 mL of trifluoroacetic acid, followed by heating and refluxing for 6 hours. Ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added thereto, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 388 mg of methyl 4-chloro-1-cyclopentyl-8-methylimidazo[1,2-a]quinoxaline-7-carboxylate as a pale yellow solid.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 6 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-793447ec17594666aa642c0842b3f1cb
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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