Cesium carbonate → HCID 178521591, compound

HRID 1926652Notes

Reaction equation

HRID 1926652 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[NH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:8][C:4]1[N:3]=[C:2]([NH:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]2)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 785042,6-DichloropyrazineHCID 178511715HCID 178511715, compound

Product 1

HCID 178521591HCID 178521591, compound

Conditions

Temperature
100 °C

Procedure

2,6 dichloropyrazine (0.50 g, 3.4 mmol), trans-4-aminocyclohexanol (0.39 g, 3.4 mmol) and cesium carbonate (2.2 g, 6.7 mmol) were added to a round bottom flask and flushed with nitrogen. DMF (4 mL) was then added and the reaction was stirred at 100° C. for 1.5 h. The reaction mixture was cooled to room temperature then diluted with EtOAc (50 mL). The mixture was filtered through celite to remove inorganic salts and the filtrate was concentrated to a crude residue. The residue was purified by silica gel chromatography to afford trans-4-[(6-chloropyrazin-2-yl)amino]cyclohexanol as a yellow oil. LRMS (ESI) calculated for C10H14ClN3O [M+H]+, 228.1; found 228.1.

Workup

  1. customflushed with nitrogen
  2. additionDMF (4 mL) was then added
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionthen diluted with EtOAc (50 mL)
  5. filtrationThe mixture was filtered through celite
  6. customto remove inorganic salts
  7. concentrationthe filtrate was concentrated to a crude residue
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-912fc0aeddea4149a71c2060b5e3734f
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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