Cyclohexene → HCID 18449239, compound

HRID 1270147Notes

Reaction equation

HRID 1270147 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:13]([O:16]C)=[N:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([F:12])[CH:6]=2.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.C1CCCCC=1>CN(C=O)C.CCOC(C)=O.CO.[Pd]>[F:12][C:7]1[CH:6]=[C:5]2[C:10]([N:11]=[C:2]([NH:25][CH2:24][C:23]3[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[C:3]3[N:4]2[C:13](=[O:16])[NH:14][N:15]=3)=[CH:9][CH:8]=1

Participants

8

Reactant 3

HCID 8079CyclohexeneHCID 754524-MethoxybenzylamineHCID 14783667HCID 14783667, compound

Product 1

HCID 18449239HCID 18449239, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g of 4-chloro-8-fluoro-1-methoxy[1,2,4]triazolo[4,3-a]quinoxaline in DMF (12.0 mL) was added 1.36 g of 4-methoxybenzylamine. This solution was stirred at room temperature for 18 hrs. and then diluted with EtOAc and washed with water and saturated lithium chloride. The extracts were dried over sodium sulfate, filtered, and concentrated and the residue was separated by silica gel chromatography to give a yellow solid. This solid was dissolved in MeOH (15 mL) and 160 mg of 10% Pd/C and 0.96 g of cyclohexene were added. This mixture was heated at reflux for 18 hrs., filtered through a pad of diatomaceous earth, and concentrated to provide an off-white solid. MS (M+H)+=340.0.

Workup

  1. washwashed with water and saturated lithium chloride
  2. dry with materialThe extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was separated by silica gel chromatography
  6. customto give a yellow solid
  7. temperatureThis mixture was heated
  8. temperatureat reflux for 18 hrs
  9. filtration, filtered through a pad of diatomaceous earth
  10. concentrationconcentrated
  11. customto provide an off-white solid

Sources & evidence

ORD record
ord-4def9f2d98d148f5a86493ffecb3c956
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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