Pyridine → HCID 54584619, compound

HRID 1818734Notes

Reaction equation

HRID 1818734 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[NH:11][N:12]=[C:13]([NH2:14])[C:8]2=[CH:7][N:6]=1.[CH2:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21].N1C=CC=CC=1>O1CCOCC1>[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[NH:11][N:12]=[C:13]([NH:14][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[C:8]2=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 178509243HCID 178509243, compound

Product 1

HCID 54584619HCID 54584619, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-ylamine (60 mg, 0.228 mmol) in 2 mL dioxane was added ethanesulfonyl chloride (22.0 uL, 0.228 mmol) and pyridine (18.5 uL, 0.228 mmol). The reaction mixture was heated to reflux with stirring for two hours, then cooled and chromatographed through silica (0%-40% EtOAc in hexanes) to give 31 mg of ethanesulfonic acid [6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-amide, MP=226.0-226.9° C., MS(M+H)=356.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. customchromatographed through silica (0%-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9c76100e1c4e485fadb444e7063aa8e3
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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