Pyridine → Methyl 3-(cyclopropyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

HRID 1403364Notes

Reaction equation

HRID 1403364 reaction equation
[CH:1]1([N:4]([CH3:20])[C:5]2[C:6](=[O:19])[NH:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=3)[CH2:3][CH2:2]1.N1C=CC=CC=1.[O:27](S(C(F)(F)F)(=O)=O)[S:28]([C:31]([F:34])([F:33])[F:32])(=O)=[O:29]>C(Cl)Cl>[CH:1]1([N:4]([CH3:20])[C:5]2[C:6]([O:19][S:28]([C:31]([F:34])([F:33])[F:32])(=[O:29])=[O:27])=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=3)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70654244Methyl 3-(cyclopropyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 86670226Methyl 3-(cyclopropyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(cyclopropyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (240 mg, 0.88 mmol) in DCM (50 mL) was added pyridine (280 mg, 3.54 mmol) and Tf2O (496 mg, 1.76 mmol). The resulting solution was stirred 3 h at room temperature and then dissolved in water/ice (100 mL), extracted with dichloromethane (3×20 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum to afford methyl 3-(cyclopropyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as a red oil (300 mg, crude), which was used to the next step directly.

Workup

  1. extractionextracted with dichloromethane (3×20 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-068ea388c7e2416cb737f15fea9b9a9e
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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