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

HRID 1192598Notizen

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-0c5b706578e946c3a2d6693d6e8b6022
Quelldatensatz: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08680108B2

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