Sodium Hydroxide → HCID 69332620, compound

HRID 915085Notes

Reaction equation

HRID 915085 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](C#N)[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.[OH-].[Na+].[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1>CN1CCN(C)C1=O.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([NH:37][CH2:36][C:35]2[CH:38]=[CH:39][C:32]([O:31][CH3:30])=[CH:33][CH:34]=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]([CH3:22])[CH3:23])[N:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 754524-MethoxybenzylamineHCID 69333289HCID 69333289, compound

Product 1

HCID 69332620HCID 69332620, compound

Reagents, catalysts & solvents 2

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
27.5 °C

Procedure

To a solution of 5-(2-bromophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2,3-pyrazinedicarbonitrile (3.00 g) in 1,3-dimethyl-2-imidazolidinone (6 ml), (4-methoxybenzyl)amine (0.96 ml) was added and the mixture was stirred at 25-30° C. for 100 hours. After addition of 0.5N aq. NaOH (15 ml), the mixture was stirred for one hour and a precipitate was collected by filtration to give a solid. The solid was dissolved in EtOAc, washed with water, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (70:30 v/v) to give 5-(2-bromophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-2-pyrazinecarbonitrile as an amorphous solid (2.58 g) containing 6-(2-bromophenyl)-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-2-pyrazinecarbonitrile.

Workup

  1. stirringthe mixture was stirred for one hour
  2. filtrationa precipitate was collected by filtration
  3. customto give a solid
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (70:30 v/v)

Sources & evidence

ORD record
ord-3fef8b8f5a8545829dcab2151e89aef4
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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