Potassium Carbonate → (5-Methyl-2H-pyrazol-3-yl)-(3-phenyl-isoquinolin-1-yl)-amine

HRID 397360Notes

Reaction equation

HRID 397360 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[NH2:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:24][C:22]1[CH:23]=[C:19]([NH:18][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:3]=2)[NH:20][N:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 119836901-chloro-3-phenylisoquinoline

Product 1

HCID 178419048(5-Methyl-2H-pyrazol-3-yl)-(3-phenyl-isoquinolin-1-yl)-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-chloro-3-phenylisoquinoline (J. Het. Chem., 20, 1983, 121-128)(0.33 g, 1.37 mmol) in DMF (anhydrous, 5 mL) was added 3-amino-5-methylpyrazole (0.27 g, 2.74 mmol) and potassium carbonate (0.57 g, 4.13 mmol)and the resulting mixture was heated at reflux for 6 hours. The reaction mixture was then cooled and solvent removed in vacuo. The residue was extracted twice with ethyl acetate and the combined organic layers washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, gradient DCM-MeOH) to afford V-1 as a colourless oil; 1H NMR (MeOD) δ2.23 (3H, s), 5.61 (1H, s), 7.41 (1H, m), 7.52(2H, m), 7.62(1H, m), 7.81(1H, m), 8.07(1H, d), 8.19(2H, m), 8.29(1H, s), 8.54 (1H, d); MS 301.2 (M+H)+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 6 hours
  3. temperatureThe reaction mixture was then cooled
  4. customsolvent removed in vacuo
  5. extractionThe residue was extracted twice with ethyl acetate
  6. washthe combined organic layers washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash chromatography (SiO2, gradient DCM-MeOH)
  11. customto afford V-1 as a colourless oil

Sources & evidence

ORD record
ord-73daa1a96cb44e1bb01a0906e4afc967
Source dataset
uspto-grants-2003_08
Patent number
US06610677B2

Reaction notes

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