Potassium Carbonate → (3s, 5r)-1-(4-Chloro-quinolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazine-2-one

HRID 1432912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432912
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH:17]([CH3:19])[NH:16][C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH:30]=[CH:31][C:32]1[S:33][C:34]([Cl:37])=[CH:35][CH:36]=1>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][C@@H:17]([CH3:19])[N:16]([CH2:29][CH:30]=[CH:31][C:32]4[S:33][C:34]([Cl:37])=[CH:35][CH:36]=4)[C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 537995313-(5-Chlorothiophen-2-yl)allyl bromideHCID 57284059(3s,5Rs)-1-(4-chloro-quinolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one

Produkt 1

HCID 91216935(3s, 5r)-1-(4-Chloro-quinolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazine-2-oneAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The crude (3S,5RS)-1-(4-chloro-quinolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one (69 mg, 0.20 mmol) obtained from above is dissolved in 1 mL of DMF. Potassium carbonate (76 mg, 0.60 mmol) is added followed by the addition of 2-(3-bromopropenyl)-5-chloro-thiophene (56 mg, 0.24 mmol). The reaction is left to stir overnight. The potassium carbonate is filtered off, and the crude material is purified. The two epimers are separated at this stage by preparative thin layer chromatography (80% EtOAc/hexane) to give a major epimer (3S, 5R)-1-(4-chloro-quinolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazine-2-one (25 mg, 26% yield) and a minor epimer (3S, 5S)-1-(4-chloro-quinolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazine-2-one (7 mg, 7.5% yield).

Aufarbeitung

  1. waitThe reaction is left
  2. filtrationThe potassium carbonate is filtered off
  3. customthe crude material is purified
  4. customThe two epimers are separated at this stage by preparative thin layer chromatography (80% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8bd1bdda2c7e4237baf58ac55f786eb3
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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