Water → HCID 69331899, compound

HRID 915020Notes

Reaction equation

HRID 915020 reaction equation
C(=O)([O-])[O-].[K+].[K+].O[C:8]1[N:9]=[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]([C:15]2[CH:16]=[CH:17][C:18](=[O:24])[N:19]([CH:21]([CH3:23])[CH3:22])[N:20]=2)=[N:12][C:13]=1[CH3:14].ICC([NH2:35])=O.O>CC(N(C)C)=O.CCOC(C)=O.CCCCCC>[NH2:35][C:8]1[N:9]=[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]([C:15]2[CH:16]=[CH:17][C:18](=[O:24])[N:19]([CH:21]([CH3:23])[CH3:22])[N:20]=2)=[N:12][C:13]=1[CH3:14]

Participants

8

Reactant 4

HCID 962WaterHCID 3727IodoacetamideHCID 11430Potassium Carbonate2×HCID 178432576HCID 178432576, compound

Product 1

HCID 69331899HCID 69331899, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
22.5 °C

Procedure

Potassium carbonate (77 mg) was added to a solution of 6-(5-hydroxy-6-methyl-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (150 mg) and iodoacetamide (95 mg) in DMA (1 ml) and the mixture was stirred at 20-25° C. for 2 hours. To the reaction mixture, potassium carbonate (235 mg) was added and heated at 150-155° C. for 2 hours. After addition of water, the mixture was extracted with CHCl3, washed with brine, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (20:80 v/v) to give 6-(5-amino-6-methyl-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone as a solid (97 mg).

Workup

  1. temperatureheated at 150-155° C. for 2 hours
  2. extractionthe mixture was extracted with CHCl3
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue

Sources & evidence

ORD record
ord-028f0fec4e214ba3827d0c12ec4c3020
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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