Piperazine → HCID 67301190, compound

HRID 1192655Notes

Reaction equation

HRID 1192655 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([Cl: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.O>[Cl: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 58368658HCID 58368658, compound

Product 1

HCID 67301190HCID 67301190, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (1.1 g, 3.1 mmol, from Example 47, Step 2), piperazine (0.40 g, 4.7 mmol) and cesium carbonate (2.8 g, 8.7 mmol) in tetrahydrofuran (20 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with water, and extracted with dichloromethane. The organic phases were combined, dried over MgSO4 and concentrated. The resulting residue was purified on silica gel (eluting with 15% methanol in dichloromethane) to give the desired product (0.57 g, 63%). LCMS calculated for C15H17ClN3O (M+H)+: m/z=290.1; Found: 290.1.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified on silica gel (eluting with 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-692f44497f274e659982e23ad851af25
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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