Cesium carbonate → HCID 21069279, compound

HRID 592783Notes

Reaction equation

HRID 592783 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[N:16]1[CH:17]=[CH:18][N:19]=[CH:20][C:15]=1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 73277ChloropyrazineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21069279HCID 21069279, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A 500-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with DMSO (250 mL), tert-butyl piperazine-1-carboxylate (15.8 g, 85.0 mmol), 2-chloropyrazine (9.7 g, 85.0 mmol), and Cs2CO3 (55.3 g, 170 mmol). The mixture was heated at 60° C. for 3 days. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 5:1 petroleum ether/ethyl acetate to afford 189a (13.3 g, 60%) as a yellow solid. MS: [M+H]+ 265.3

Workup

  1. customA 500-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureAfter this time the reaction was cooled to room temperature
  3. filtrationIt was then filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with 5:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-e1e9c67039af408da2e59677aeae9237
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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