Hydrogen Peroxide → HCID 71554403, compound

HRID 1776441Notes

Reaction equation

HRID 1776441 reaction equation
[CH2:1]([O:3][C:4]1[CH:38]=[C:37]([F:39])[C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:21]([O:31][CH2:32][CH2:33][S:34]([CH3:36])=[O:35])=[CH:20][N:19]=3)=[N:10]2)=[C:6]([F:40])[CH:5]=1)[CH3:2].OO.CC[O:45]C(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([F:40])[C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)[C:21]([O:31][CH2:32][CH2:33][S:34]([CH3:36])(=[O:45])=[O:35])=[CH:20][N:19]=3)=[N:10]2)=[C:37]([F:39])[CH:38]=1)[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 5462977Diethyl azodicarboxylateHCID 71554404HCID 71554404, compound

Product 1

HCID 71554403HCID 71554403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

100 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-5-[2-(methylsulfinyl)ethoxy]-N-(pyridin-4-yl)pyrimidin-4-amine (36-1, 0.177 mmol, 1.0 eq.) were dissolved in 0.9 ml of anhydrous tetrahydrofuran. 0.09 ml of aqueous hydrogen peroxide (30%, 0.886 mmol, 5.0 eq.) and 37.0 mg Diethylazodicarboxylate were added. The reaction mixture was stirred at 50° C. for 2 h. A white precipitate was filtered off and purified by flash chromatography to yield 18.1 mg (0.03 mmol, 17.6%) of the analytically pure target compound.

Workup

  1. filtrationA white precipitate was filtered off
  2. custompurified by flash chromatography
  3. customto yield 18.1 mg (0.03 mmol, 17.6%) of the analytically pure target compound

Sources & evidence

ORD record
ord-3c6187af687946dc88d9cfcc08ad1203
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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