Hydrogen Peroxide → HCID 66692036, compound

HRID 1773636Notes

Reaction equation

HRID 1773636 reaction equation
[CH:1]1([NH:4][C:5](=[O:37])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([S:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=5)[CH:19]=[C:20]([NH:21][CH2:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:36])[CH2:3][CH2:2]1.C(#N)C1C=CN=CC=1.OO.S([O-])([O-])(=[O:50])=S.[Na+].[Na+]>ClCCl.C[Re](=O)(=O)=O>[CH:1]1([NH:4][C:5](=[O:37])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([S:28]([C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=5)=[O:50])[CH:19]=[C:20]([NH:21][CH2:22][CH2:23][C:24]([F:26])([F:27])[F:25])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:36])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 75064-CyanopyridineHCID 24477Sodium ThiosulfateHCID 66691934HCID 66691934, compound

Product 1

HCID 66692036HCID 66692036, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 50 mg (121 μmol) N-cyclopropyl-4-{6-[(3-fluorophenyl) sulfanyl]-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-b]pyridazin-3-yl}-2-methylbenzamide, which was prepared according to intermediate example 209 in 1.0 mL dichloromethane were added 0.71 mg methyl(trioxo)rhenium, 1.77 mg isonicotinonitrile and 58 μL aqueous hydrogen peroxide (30%). The mixture was stirred for two days at 23° C., poured into sodium thiosulfate solution and extracted with dichloromethane. The organic phase was dried over sodium sulfate. After filtration and removal of solvent the residue was purified by chromatography to give 14.9 mg (53%) of the title compound A and 4.5 mg (8%) of the title compound B.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationAfter filtration and removal of solvent the residue
  4. customwas purified by chromatography

Sources & evidence

ORD record
ord-2fc5fe9788454b0883294ba743742cf4
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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