Reaktion #217620

Reaktionsgleichung

4-bromo-2-fluorobenzenesulfonyl chloride

5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline

5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

morpholinomethyl-polystyrene

→

title compound

4-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-fluorobenzenesulfonamide

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe resin was then filtered off
2. 2
   Sonstigethe solvent evaporated in vacuo
3. 3
   Wascheneluting first with methanol
4. 4
   Sonstigesolvent evaporated in vacuo
5. 5
   Sonstigeto afford a crude product which
6. 6
   Sonstigewas dry
7. 7
   Sonstigepurified further by chromatography
8. 8
   Sonstigean elution gradient of 0 to 10% methanol in dichloromethane The relevant fractions were collected
9. 9
   Sonstigesolvent evaporated

Vorschrift

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (1.20 g, 5.09 mmol) in dichloromethane (35 ml) was treated with morpholinomethyl-polystyrene HL resin (2.43 g, 4.2 mmol/g loading, 10.2 mmol) followed by 4-bromo-2-fluorobenzenesulfonyl chloride (2.79 g, 10.2 mmol). The resulting solution was stirred at room temperature overnight, the resin was then filtered off, the solvent evaporated in vacuo and the residue was then passed through an SCX column eluting first with methanol and then by 2M ammonia in methanol. The basic fractions were combined and solvent evaporated in vacuo to afford a crude product which was dry loaded onto a column and purified further by chromatography using a Flashmaster and an elution gradient of 0 to 10% methanol in dichloromethane The relevant fractions were collected, combined and solvent evaporated to afford the title compound (E103). MS (ES+) m/e 472/474 [M+H]+.

Quelle