Acetic Acid → HCID 69333276, compound

HRID 915037Notes

Reaction equation

HRID 915037 reaction equation
[NH2:1][C:2]1[C:3]([C:25]#[N:26])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:7]=1.CC(O)=[O:29].O.C([O-])(O)=O.[Na+]>Br.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:25]([NH2:26])=[O:29])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 69332723HCID 69332723, compound

Product 1

HCID 69333276HCID 69333276, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-5-(4-fluorophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarbonitrile (30 mg) in 28% hydrogen bromide solution of AcOH (2 ml) was stirred at 25° C. for 3 hours. Water, aq. NaHCO3 and EtOAc were added to the reaction mixture. The organic layer was separated, and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of CHCl3 and MeOH. The fractions were concentrated in vacuo to obtain 3-amino-5-(4-fluorophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarboxamide (30 g) as white powder.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluted with a mixture of CHCl3 and MeOH
  6. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-423610b02c314db096c9c813aefed529
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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