Piperazine → 1-(5-Fluoro-8-piperazin-1-ylquinolin-7-yl)ethanone

HRID 1192693Notes

Reaction equation

HRID 1192693 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([F:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl>[F:17][C:10]1[CH:9]=[C:8]([C:18](=[O:20])[CH3:19])[C:7]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

Participants

6

Reactant 3

HCID 4837PiperazineHCID 10796Cesium carbonateHCID 583685787-Acetyl-5-fluoroquinolin-8-yl trifluoromethanesulfonate

Product 1

HCID 583686261-(5-Fluoro-8-piperazin-1-ylquinolin-7-yl)ethanoneYield 10.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 7-acetyl-5-fluoroquinolin-8-yltrifluoromethanesulfonate (1.00 g, 2.96 mmol, from Example 53, Step 2), piperazine (0.511 g, 5.93 mmol), and cesium carbonate (2.90 g, 8.90 mmol) in tetrahydrofuran (30 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over sodium sulfate and evaporated to dryness. The resulting residue was purified on silica gel, eluting with 0 to 20% methanol in dichloromethane, to give the desired product (82 mg, 10%). LCMS calculated for C15H17FN3O (M+H)+: m/z=274.1; Found: 274.1.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe resulting residue was purified on silica gel
  7. washeluting with 0 to 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-8d0918cf1feb47f3856f0e0f88cb4b94
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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