HCID 69332557, compound → HCID 69331987, compound

HRID 915086Notes

Reaction equation

HRID 915086 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([NH:26]CC2C=CC(OC)=CC=2)[C:11]([C:24]#[N:25])=[N:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[N:15]=1.BrC1C=CC=CC=1C1N=C(C#N)C(NCC2C=CC(OC)=CC=2)=NC=1C1C=CC(=O)N(C(C)C)N=1>C(Cl)(Cl)Cl.O>[NH2:26][C:10]1[C:11]([C:24]#[N:25])=[N:12][C:13]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[N:9]=1

Participants

5

Reactant 2

HCID 69332557HCID 69332557, compoundHCID 69332620HCID 69332620, compound

Product 1

HCID 69331987HCID 69331987, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
27.5 °C

Procedure

To a solution of 5-(2-bromophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-2-pyrazinecarbonitrile (2.05 g) containing 6-(2-bromophenyl)-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-2-pyrazinecarbonitrile in CHCl3 (60 ml), water (3 ml) and 2,3-dichloro-5,6-dicyano-1,4-benzoqinone (2.63 g) were added and the mixture was stirred at 25-30° C. for 24 hours. The mixture was washed with 1N aq. NaOH, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel. By elution of a mixture of n-hexane and EtOAc (70:30 v/v) was obtained 3-amino-5-(2-bromophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarbonitrile as a solid (941 mg) and by elution of a mixture of n-hexane and EtOAc (50:50 v/v) was obtained 3-amino-6-(2-bromophenyl)-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarbonitrile as a solid (92 mg).

Workup

  1. additionwere added
  2. washThe mixture was washed with 1N aq. NaOH
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customThe residue was purified by column chromatography on silica gel
  7. washBy elution of a mixture of n-hexane

Sources & evidence

ORD record
ord-75112fd0b5104e94a45f0e72d707b5d5
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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