Benzylamine → HCID 18449179, compound

HRID 1270146Notes

Reaction equation

HRID 1270146 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.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C.CCOC(C)=O.Br.CC(O)=O>[CH2:18]([NH:25][C:2]1[C:3]2[N:4]([C:13](=[O:16])[NH:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([F:12])[CH:6]=2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 14783667HCID 14783667, compound

Product 1

HCID 18449179HCID 18449179, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

To a solution of 500 mg of 4-chloro-8-fluoro-1-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline in DMF (6.0 mL) was added 637 mg of benzylamine. 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 material was dissolved in a 1:1.5 mixture of 48% HBr/AcOH, and refluxed for 12 hrs. The reaction mixture was concentrated and the residue was recrystallized from MeOH to afford the title compound as a yellow solid. MS (M+H)+=310.0.

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. temperaturerefluxed for 12 hrs
  8. concentrationThe reaction mixture was concentrated
  9. customthe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-3a2fcabd3e3a4cf5bd011936bcf4020d
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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