2-Fluoroaniline → N-(2-fluorophenyl)-3-[(8aS)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

HRID 400504

Reaktionsgleichung

Reaktionsgleichung von HRID 400504
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].[CH2:14]1[NH:19][CH2:18][CH2:17][N:16]2[CH2:20][CH2:21][CH2:22][C@@H:15]12.[F:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26]>ClCCl>[F:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH:26][S:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([N:19]2[CH2:18][CH2:17][N:16]3[CH2:20][CH2:21][CH2:22][C@H:15]3[CH2:14]2)=[O:9])[CH:6]=1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 95842-FluoroanilineHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 781249(6S)-1,4-Diazabicyclo(4.3.0)nonane

Produkt 1

HCID 46851310N-(2-fluorophenyl)-3-[(8aS)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 3-(chlorosulfonyl)benzoyl chloride (0.521 g, 2.18 mmol) in anhydrous dichloromethane (10 mL) was added (S)-octahydropyrrolo[1,2-a]pyrazine (0.250 g, 1.98 mmol) in dichloromethane (4 mL) slowly over 10 minutes at room temperature. The mixture was stirred at room temperature for 5 hours. Then 2-fluoroaniline (1.54 g, 13.87 mmol) was added. The mixture was stirred at room temperature overnight and then concentrated. The residue was purified by chromatography on silica gel (dichloromethane, then methanol/dichloromethane=1:10) to give the titled compound.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel (dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-d942abd221534db3bb1ed208b2cab874
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741899B2

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