6-Bromoquipazine → (2S)-2-{[4-(6-Bromoquinolin-2-yl)piperazin-1-yl]methyl}-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinoline

HRID 860010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860010
BrC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[C:34]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH:33]=[CH:32]2.C(=O)(O)[O-].[Na+]>CS(C)=O>[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[C:34]([N:39]1[CH2:40][CH2:41][N:42]([CH2:12][C@@H:13]3[O:27][C:17]4=[C:18]5[C:23](=[CH:24][CH:25]=[C:16]4[O:15][CH2:14]3)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]5)[CH2:43][CH2:44]1)[CH:33]=[CH:32]2

Komponenten

5

Edukt 3

HCID 1302616-BromoquipazineHCID 516892Sodium BicarbonateHCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate

Produkt 1

HCID 44219922(2S)-2-{[4-(6-Bromoquinolin-2-yl)piperazin-1-yl]methyl}-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolineAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4 bromobenzene sulfonate (2.31 g, 5.13 mmol) in dimethylsulfoxide (123 mL) is added the 6-bromo-2-piperazin-1-yl-quinoline of Step B (1.5 g, 5.13 mmol) and the mixture is heated at 75° C. under nitrogen overnight. The mixture is poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extracts are dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is flash chromatographed on silica gel Merck-60 using a gradient of methanol (0.5–2%) in ethyl acetate-hexane (55:45) to provide the title compound as an off-white solid (1.02 g), m.p. 153–154° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts are dried over anhydrous magnesium sulfate
  3. customevaporated to dryness
  4. customchromatographed on silica gel Merck-60

Quellen und Nachweise

ORD-Eintrag
ord-bb354057eb944558a4c9fedc147cdf05
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153849B2

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