Tert-butyl (6-(3-hydroxy-4-methylpent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate → Tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

HRID 2176614Notes

Reaction equation

HRID 2176614 reaction equation
[OH:1][CH:2]([CH:23]([CH3:25])[CH3:24])[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:12][N:13]=2)[N:10]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:24][CH:23]([CH3:25])[C:2](=[O:1])[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[N:12][N:13]=2)[N:10]=1

Participants

4

Reactant 1

HCID 57691276Tert-butyl (6-(3-hydroxy-4-methylpent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Product 1

HCID 57691360Tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamateYield 50.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (6-(3-hydroxy-4-methylpent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (1.82 g, 5.27 mmol) and manganese dioxide (activated) (9.16 g, 105 mmol) were dissolved in DCM (263 mL) and stirred at room temperature over two days. Additional manganese dioxide (activated) (4.58 g, 52.7 mmol) was added and stirring continued overnight. The reaction mixture was filtered over a plug of Celite and washed with DCM to yield tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.917 g, 50.7% yield) after concentration in vacuo.

Workup

  1. stirringstirring continued overnight
  2. filtrationThe reaction mixture was filtered over a plug of Celite
  3. washwashed with DCM

Sources & evidence

ORD record
ord-577c9444792642e895f2e510c66c70ff
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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