Hydrogen Peroxide → HCID 118092959, compound

HRID 2207409Notes

Reaction equation

HRID 2207409 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[N:23][CH:24]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.[OH:27]O.[OH-].[Na+]>CS(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([NH2:26])=[O:27])=[N:23][CH:24]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 131735908HCID 131735908, compound

Product 1

HCID 118092959HCID 118092959, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of with 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carbonitrile (50.0 mg, 0.141 mmol) in DMSO (281 μL) was slowly added to a solution of hydrogen peroxide (10.0 μL, 0.326 mmol) and sodium hydroxide (5 M, 56.3 μL, 0.281 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was filtered, diluted with DMF, and directly purified by reverse phase HPLC (5-95% acetonitrile in water+0.5% TFA) to yield 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carboxamide. MS APCI calc'd for C18H15F3N5O [M+H]+ 374. found 374. 1H NMR (500 MHz, CDCl3) δ 8.85 (s, 1H), 8.65 (d, J=5.6 Hz, 1H), 8.27 (d, J=8.6 Hz, 1H), 8.09 (d, J=8.5, 1H), 7.98 (s, 1H), 7.39 (s, 1H), 7.19 (s, 1H), 7.09 (d, J=5.5 Hz, 1H), 2.47 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with DMF
  3. customdirectly purified by reverse phase HPLC (5-95% acetonitrile in water+0.5% TFA)

Sources & evidence

ORD record
ord-b921bc4e5a3e4e4db267f2be22763b53
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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