Pyridine → HCID 178522645, compound

HRID 1818733Notes

Reaction equation

HRID 1818733 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.N1C=CC=[CH:22][CH:21]=1.[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]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][C:29]([CH:26]3[CH2:28][CH2:27][CH2:22][CH2:21]3)=[O:30])[C:8]2=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 178509243HCID 178509243, compound

Product 1

HCID 178522645HCID 178522645, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-ylamine (45 mg, 0.17 mmol) in 1.7 mL of dioxane was added 14 uL pyridine and cyclopropane carbonyl chloride (21 uL, 0.17 mmol). The reaction mixture was heated to reflux for three hours, then cooled and chromatographed through silica (20%-50% EtOAc in hexanes) to afford 32 mg of cyclopentanecarboxylic acid [6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-amide, MP=206.3-207.51° C., MS (M+H)=360.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for three hours
  3. temperaturecooled
  4. customchromatographed through silica (20%-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cbbda30b7529477581803e3735cf113a
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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