Acetic Acid → 3-Amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarboxamide

HRID 915024Notes

Reaction equation

HRID 915024 reaction equation
[NH2:1][C:2]1[C:3]([C:24]#[N:25])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.CC(O)=[O:28].C([O-])([O-])=O.[Na+].[Na+].CCCCCC>Br.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:24]([NH2:25])=[O:28])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8058HexaneHCID 10340Sodium CarbonateHCID 693314823-Amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile

Product 1

HCID 116532023-Amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarboxamide

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
27.5 °C

Procedure

A suspension of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile (143 mg) in 25% hydrogen bromide solution of AcOH (1.5 ml) was stirred at 25-30° C. for 2 hours. The reaction mixture was poured into a mixture of Na2CO3 (2 g) and ice-water (30 g), extracted with CHCl3, 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 (60:40 v/v) to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarboxamide as a solid (136 mg).

Workup

  1. extractionextracted with CHCl3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue

Sources & evidence

ORD record
ord-458df124b2754dc98be66ec366eaf8a0
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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