Hydrogen Peroxide → HCID 54590915, compound

HRID 2276765Notes

Reaction equation

HRID 2276765 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:26])([CH3:25])[CH2:9][NH:10][C:11]2[N:16]=[N:15][C:14]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[N:13][CH:12]=2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:28].[K+].[K+].OO>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:26])([CH3:25])[CH2:9][NH:10][C:11]2[N:16]=[N:15][C:14]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]([NH2:21])=[O:28])=[N:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67453473HCID 67453473, compound

Product 1

HCID 54590915HCID 54590915, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-(6-(2-(4-fluorophenyl)-2-methylpropylamino)-1,2,4-triazin-3-yl)benzonitrile (220 mg, 0.60 mmol) in DMSO (3.0 mL) was added K2CO3 (300 mg, 2.2 mmol) and 30% hydrogen peroxide (0.60 mL, 7.5 mmol). The mixture was stirred 24 h and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×) and the combined organics were dried over Na2SO4 and evaporated to dryness in vacuo. Purification using silica gel chromatography (0-100% EtOAc/hexanes) gave the desired product (17 mg), m/z=366.1 [M+H].

Workup

  1. custompartitioned between EtOAc and water
  2. extractionThe aqueous layer was extracted with EtOAc (2×)
  3. dry with materialthe combined organics were dried over Na2SO4
  4. customevaporated to dryness in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-1db64adf850d4b438796096e9146d5eb
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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