1-(2-Hydroxyethyl)piperazine → HCID 58368549, compound

HRID 1192598Notes

Reaction equation

HRID 1192598 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.[N:23]1([CH2:29][CH2:30][OH:31])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:17][C:10]1[CH:9]=[C:8]([C:18](=[O:20])[CH3:19])[C:7]([N:26]2[CH2:27][CH2:28][N:23]([CH2:29][CH2:30][OH:31])[CH2:24][CH2:25]2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

Participants

8

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 58368658HCID 58368658, compound

Product 1

HCID 58368549HCID 58368549, compoundYield 14.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.34 mmol, from Example 47, Step 2), 1-piperazineethanol (0.053 g, 0.41 mmol), palladium acetate (1.5 mg, 0.0068 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.3 mg, 0.010 mmol), and cesium carbonate (0.31 g, 0.95 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with water, dried over MgSO4, evaporated to dryness. The resulting residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane) to give the desired product (16 mg, 14%). LCMS calculated for C17H21ClN3O2 (M+H)+: m/z=334.1; Found: 334.0.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-0c5b706578e946c3a2d6693d6e8b6022
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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