Ethanamine, 2-(4-methylphenoxy)-, hydrochloride (1:1) → HCID 68677501, compound

HRID 2233044Notes

Reaction equation

HRID 2233044 reaction equation
[C:1]([C:5]1[N:6]=[C:7](Cl)[C:8]2[N:9]([C:11](=[O:14])[NH:12][N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][NH2:26])=[CH:19][CH:18]=1>CN(C=O)C>[C:1]([C:5]1[N:6]=[C:7]([NH:26][CH2:25][CH2:24][O:23][C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)[C:8]2[N:9]([C:11](=[O:14])[NH:12][N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 17233812Ethanamine, 2-(4-methylphenoxy)-, hydrochloride (1:1)HCID 68676527HCID 68676527, compound

Product 1

HCID 68677501HCID 68677501, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 60 mg of 6-tert-butyl-8-chloro-2H-[1,2,4]triazolo[4,3-a]pyrazin-3-one and 100 mg of 2-p-tolyloxy-ethylamine hydrochloride in DMF (2.0 mL) was added 60 mg of TEA. The mixture was heated to 80° C. for three h and then was cooled to ambient temperature and partitioned between EtOAc and water. The organic layer was washed with sat. sodium chloride solution and then dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to afford the title compound as a white solid. MS (M+H+)=342.5.

Workup

  1. temperaturewas cooled to ambient temperature
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with sat. sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-753eecbcf58146e0b9edfc086a5ad1ef
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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