Pyridine → HCID 86670562, compound

HRID 1403403Notes

Reaction equation

HRID 1403403 reaction equation
[O:1]=[C:2]1[C:11]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=2)[NH:3]1.N1C=CC=CC=1.[O:28](S(C(F)(F)F)(=O)=O)[S:29]([C:32]([F:35])([F:34])[F:33])(=O)=[O:30]>ClCCl>[N:12]1([C:11]2[C:2]([O:1][S:29]([C:32]([F:35])([F:34])[F:33])(=[O:30])=[O:28])=[N:3][C:4]3[C:9]([N:10]=2)=[CH:8][C:7]([C:18]([O:20][CH3:21])=[O:19])=[CH:6][CH:5]=3)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70665235HCID 70665235, compound

Product 1

HCID 86670562HCID 86670562, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-oxo-3-(piperidin-1-yl)-1,2-dihydroquinoxaline-6-carboxylate (200 mg, 0.70 mmol) in dichloromethane (30 mL) was added pyridine (220 mg, 2.8 mmol) and then Tf2O (393 mg, 1.4 mmol) was added dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature and then quenched by the addition of water (50 mL), extracted with dichloromethane (3×10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford methyl 3-(piperidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as red solid (280 mg, crude).

Workup

  1. stirringThe resulting solution was stirred overnight at room temperature
  2. customquenched by the addition of water (50 mL)
  3. extractionextracted with dichloromethane (3×10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f403cf0c51f34f26be89f51001231578
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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