Sodium Hydroxide → HCID 69331987, compound

HRID 915081Notes

Reaction equation

HRID 915081 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]=CN(C)C)[C:11]([C:19]#[N:20])=[N:10][C:9]=1[C:21]1[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH:28]([CH3:30])[CH3:29])[N:22]=1.[OH-].[Na+]>O.Cl.O1CCOCC1>[NH2:14][C:12]1[C:11]([C:19]#[N:20])=[N:10][C:9]([C:21]2[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH:28]([CH3:30])[CH3:29])[N:22]=2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[N:13]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 69332535HCID 69332535, compound

Product 1

HCID 69331987HCID 69331987, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of N′-[6-(2-bromophenyl)-3-cyano-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinyl]-N,N-dimethylimidoformamide (285 mg) in a mixture of water (2 ml) and 4N hydrogen chloride in dioxane (6 ml) was stirred at 20-25° C. for 18 hours. After addition of water (18 ml), the mixture was neutralized with 1N aq. NaOH to give a solid. The solid was collected by filtration and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v) to give 3-amino-5-(2-bromophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarbonitrile as a solid (163 mg).

Workup

  1. customto give a solid
  2. filtrationThe solid was collected by filtration
  3. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v)

Sources & evidence

ORD record
ord-98c54a195d4c4e74b6b0a3faabfa6ac3
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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