Triethylamine → N-[1-(4'-chloro-2'-fluoro-1,1'-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamide

HRID 2181927

Reaktionsgleichung

Reaktionsgleichung von HRID 2181927
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]([NH2:28])[CH3:27])=[C:16]([F:29])[CH:15]=1.C(N(CC)CC)C>C(#N)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]([NH:28][S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:11])=[O:10])[CH3:27])=[C:16]([F:29])[CH:15]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 22482361HCID 22482361, Verbindung

Produkt 1

HCID 22482365N-[1-(4'-chloro-2'-fluoro-1,1'-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamideAusbeute 103,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

3-Methoxybenzenesulfonyl chloride (331 mg, 1.6 mmol) was added to a solution of 1-(4′-chloro-2′-fluoro-1,1′-biphenyl-2-yl)ethylamine (400 mg, 1.6 mmol) and triethylamine (246 μL, 1.7 mmol) in acetonitrile. The reaction was mixed at room temperature for 24 hours, afterwhich the acetonitrile was removed in vacuo. The remaining solid was dissolved in dichloromethane and purified by preparative liquid chromatogrpahy on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 5%-50% methyl tert-butyl ether in hexane (35 min), to afford the the desired product (694 mg, 99%) as a white solid;

Aufarbeitung

  1. customwas removed in vacuo
  2. dissolutionThe remaining solid was dissolved in dichloromethane
  3. custompurified by preparative liquid chromatogrpahy on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  4. washeluting with a gradient of 5%-50% methyl tert-butyl ether in hexane (35 min)

Quellen und Nachweise

ORD-Eintrag
ord-b214738d486547c9bd54ab946152c525
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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