Sodium Hydroxide → 3-[Bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarboxamide

HRID 915042Notes

Reaction equation

HRID 915042 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:9]2[C:10]([C:31]#[N:32])=[N:11][C:12]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH:28]([CH3:30])[CH3:29])[N:22]=3)=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:5][CH:4]=1.[OH-:44].[Na+]>O1CCOCC1>[CH3:41][O:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:43][CH:42]=2)[C:9]2[C:10]([C:31]([NH2:32])=[O:44])=[N:11][C:12]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH:28]([CH3:30])[CH3:29])[N:22]=3)=[C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:14]=2)=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 693319503-[Bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile

Product 1

HCID 693314613-[Bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 3-[bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile (3.00 g) in a mixture of 2N aq. NaOH (30 ml) and dioxane (21 ml) was refluxed for 36 hours. After cooling, the mixture was extracted with EtOAc, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (20:80 v/v) to give a solid. The solid was crystallized from a mixture of n-hexane and acetone to give 3-[bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarboxamide (2.56 g).

Workup

  1. temperaturewas refluxed for 36 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (20:80 v/v)
  7. customto give a solid
  8. customThe solid was crystallized from a mixture of n-hexane and acetone

Sources & evidence

ORD record
ord-0c5045c4dea24c65b65cb1c317af4a01
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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