Hydrochloric Acid → HCID 69104183, compound

HRID 2217246Notes

Reaction equation

HRID 2217246 reaction equation
[NH2:1][C:2]1[C:3](C(N)=O)=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:7]=1.[OH-].[Na+].Cl>O1CCOCC1.ClC1C=CC=CC=1Cl>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69103739HCID 69103739, compound

Product 1

HCID 69104183HCID 69104183, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 72391,2-DichlorobenzeneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspention of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-(2-pyridyl)-2-pyrazinecarboxamide (52 mg) in dioxane (0.5 ml) was added an aq. NaOH (2M, 1 ml) and this solution was heated at 100° C. for 4 hours. This reaction mixture was cooled to room temperature and the pH of this solution was adjusted to 2.5 with 2N aq. HCl. This solution was evaporated under reduced pressure to give yellow solid. A suspension of this yellow solid in 1,2-dichlorobenzene (2 ml) was heated at 200° C. and stirred for 4 hours. This reaction mixture was cooled to room temperature. To this solution was added IPE and stirred at room temperature for 1 hour. The precipitate was collected by filtration and washed with IPE. The residual solid was placed on a column of silica-gel and eluted with CHCl3—MeOH—28% aq. ammonia (15:1:0.1). The eluent was evaporated and the residue was purified by recrystallization from EtOAc-IPE to give 5-[5-amino-3-(2-pyridyl)-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (5 mg) as a pale yellow crystal.

Workup

  1. temperatureThis reaction mixture was cooled to room temperature
  2. customThis solution was evaporated under reduced pressure
  3. customto give yellow solid
  4. temperaturewas heated at 200° C.
  5. temperatureThis reaction mixture was cooled to room temperature
  6. additionTo this solution was added IPE
  7. stirringstirred at room temperature for 1 hour
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with IPE
  10. washeluted with CHCl3—MeOH—28% aq. ammonia (15:1:0.1)
  11. customThe eluent was evaporated
  12. customthe residue was purified by recrystallization from EtOAc-IPE

Sources & evidence

ORD record
ord-72224d0702aa4405aedafdc8a15d15c3
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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