Ethanol → HCID 57438766, compound

HRID 2233093Notes

Reaction equation

HRID 2233093 reaction equation
C[NH2:2].CCO.CO[C:8]([C:10]1[C:11]2[N:12]([CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:18]=2)[CH:13]=[CH:14][N:15]=1)=O>>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:18]=[C:11]3[C:10]([CH2:8][NH2:2])=[N:15][CH:14]=[CH:13][N:12]3[CH:16]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 57438736Methyl 2-(4-fluorophenyl)imidazo[1,2-a]pyrazine-8-carboxylate

Product 1

HCID 57438766HCID 57438766, compoundYield 91%

Conditions

Temperature
100 °C

Procedure

In a sealed tube vessel was added 8M methylamine in EtOH (10 mL, 80 mmol) and 8-chloro-2-(4-fluorophenyl)-imidazo[1,2-a]pyrazine (prepared from general procedure B using 3-chloropyrazin-2-ylamine and 2-bromo-1-(4-fluorophenyl)-ethanone; 2.30 g, 9.3 mmol). The mixture was heated at about 100° C. for about 1 h. The mixture was cooled to ambient temperature and the reaction mixture was partitioned between water and dichloromethane. The layers were separated. The organic layer was washed with brine, dried over Na2SO4, and filtered prior to concentrating under reduced pressure. The product was purified by silica gel chromatography using EtOAc/heptane (1:1) to give the title compound as a beige solid (2.05 g, 91%): LC/MS (Table 1, Method a) Rt=1.70 min; MS m/z: 243.3 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe reaction mixture was partitioned between water and dichloromethane
  3. customThe layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationto concentrating under reduced pressure
  8. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-517b13d41dbc4cfd9e5e539e629e458d
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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