Hydrogen Peroxide → 2-[3-(2,2-Dimethylpropanoylamino)-4-(trifluoromethyl)phenyl]imidazo[2,1-f]pyridazine-6-carboxamide

HRID 539754Notes

Reaction equation

HRID 539754 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]2=[N:9][C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:25]([F:28])([F:27])[F:26])=[C:16]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:17]=3)=[CH:11][N:5]2[N:4]=1)#[N:2].CC[OH:31].CS(C)=O.[OH-].[Na+].OO>O>[CH3:21][C:20]([CH3:23])([CH3:22])[C:19]([NH:18][C:16]1[CH:17]=[C:12]([C:10]2[N:9]=[C:6]3[N:5]([CH:11]=2)[N:4]=[C:3]([C:1]([NH2:2])=[O:31])[CH:8]=[CH:7]3)[CH:13]=[CH:14][C:15]=1[C:25]([F:28])([F:26])[F:27])=[O:24]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22338741Dimethylsulfoxide ethanolHCID 67983247N-[5-(6-cyanoimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

Product 1

HCID 679827882-[3-(2,2-Dimethylpropanoylamino)-4-(trifluoromethyl)phenyl]imidazo[2,1-f]pyridazine-6-carboxamideYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An 8 mL vial is charged with N-[5-(6-cyanoimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.019 g, 0.05 mmol), EtOH-DMSO (1.2 mL, 5:1), NaOH (0.1 mL, 1M in water), and H2O2 (0.1 mL, 30% in water). The mixture is stirred for 2 hr at room temp, diluted with water (4 mL), extracted EtOAc (2×) and CH2Cl2 (1 x). Organics are dried, concentrated onto celite and purified on silica (0-100% EtOAc in CH2Cl2) to give the title compound (12 mg, 60% yield). LCMS m/z=406.5 [M+H]+, tR=2.12 min. (compound same as Example 180)

Workup

  1. extractionextracted EtOAc (2×) and CH2Cl2 (1 x)
  2. customOrganics are dried
  3. concentrationconcentrated onto celite
  4. custompurified on silica (0-100% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-e86ba2833945498ca86d2c9b86c1b302
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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