Sodium Hydroxide → tert-butyl N-[[6-[(E)-hydroxyiminomethyl]-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl]carbamate

HRID 40393Notes

Reaction equation

HRID 40393 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10][N:11]=2)[N:8]=1)=O.Cl.[NH2:22][OH:23].[OH-].[Na+]>C1COCC1>[OH:23]/[N:22]=[CH:1]/[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10][N:11]=2)[N:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 57691111Tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Product 1

HCID 135987477tert-butyl N-[[6-[(E)-hydroxyiminomethyl]-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl]carbamateYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (400 mg, 1.44 mmol) and hydroxylamine hydrochloride (200 mg, 2.86 mmol) were combined in a flask with 25 mL of THF and 25 mL of 1 N NaOH solution. Stirred at rt for 1 h. Then added dichloromethane (50 mL) and extracted the aqueous layer 3 times with DCM (50 mL), dried over Na2SO4 and concentrated. Purified the oxime via MPLC (DCM/MeOH+1% NH4OH) to give title compound (200 mg, 47% yield) as a tan solid.

Workup

  1. extractionThen added dichloromethane (50 mL) and extracted the aqueous layer 3 times with DCM (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurified the oxime via MPLC (DCM/MeOH+1% NH4OH)

Sources & evidence

ORD record
ord-c7ebc6b0d3594bb1b35de7076c46984f
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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