Water → HCID 57917366, compound

HRID 69301Notes

Reaction equation

HRID 69301 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[CH:19][C:20]5[N:21]([C:23]([CH:26]=[CH2:27])=[CH:24][N:25]=5)[CH:22]=4)=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1.[OH2:28].[O-][Mn](=O)(=O)=O.[K+].[OH-:35].[Na+]>O1CCOCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[CH:19][C:20]5[N:21]([C:23]([CH:26]([OH:35])[CH2:27][OH:28])=[CH:24][N:25]=5)[CH:22]=4)=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 57917377HCID 57917377, compound

Product 1

HCID 57917366HCID 57917366, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-(1-Methyl-1H-pyrazol-4-yl)-3-(3-vinyl-imidazo[1,2-a]pyridin-6-ylmethyl)-imidazo[1,2-b]pyridazine (Example 299, 49 mg, 0.138 mmol) was dissolved in dioxane (0.69 mL) and water (0.69 mL) then KMnO4 (21.8 mg, 0.138 mmol) and 2.5 M NaOH solution (0.165 mL, 0.414 mmol) were added. The RM was stirred at rt for 3 h. It was then filtered through Celite and the solvent was removed. The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA). The fractions were joined and were lyophilized. The residue was dissolved in MeOH and it was passed through an SPE cartridge of HCO3− to remove the TFA salt. The filtrate was evaporated and the residue was triturated with pentane. The precipitate was filtered off and dried to afford the title compound as a white solid (tR 0.3 min (conditions 2), MH+=390).

Workup

  1. filtrationIt was then filtered through Celite
  2. customthe solvent was removed
  3. customThe residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)
  4. dissolutionThe residue was dissolved in MeOH
  5. customto remove the TFA salt
  6. customThe filtrate was evaporated
  7. customthe residue was triturated with pentane
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-07c36265571f4936981bf13ddc80f4a7
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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