4-(Trifluoromethyl)aniline → 3-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]-N-[4-(trifluoromethyl)phenyl]benzenesulfonamide

HRID 400493

Reaktionsgleichung

Reaktionsgleichung von HRID 400493
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.C(=O)([O-])[O-].[Na+].[Na+].[F:29][C:30]([F:39])([F:38])[C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>ClCCl.CO>[CH2:14]1[N:19]([C:8]([C:7]2[CH:6]=[C:5]([S:2]([NH:35][C:34]3[CH:36]=[CH:37][C:31]([C:30]([F:29])([F:38])[F:39])=[CH:32][CH:33]=3)(=[O:4])=[O:3])[CH:13]=[CH:12][CH:11]=2)=[O:9])[CH2:18][CH2:17][N:16]2[CH2:20][CH2:21][CH2:22][C@H:15]12

Komponenten

7

Edukt 4

HCID 99644-(Trifluoromethyl)anilineHCID 10340Sodium Carbonate2×HCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazine

Produkt 1

HCID 468533803-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]-N-[4-(trifluoromethyl)phenyl]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 3-(chlorosulfonyl)benzoyl chloride (0.359 g, 1.5 mmol) in anhydrous dichloromethane (80 mL) was added (R)-octahydropyrrolo[1,2-a]pyrazine (0.189 g, 1.5 mmol) in dichloromethane (4 mL) slowly over 10 minutes at room temperature. Then sodium carbonate (0.32 g, 2 mmol) was added, and the mixture was stirred at room temperature for 5 hours. Subsequently 4-(trifluoromethyl)aniline (2.42 g, 15 mmol) was added. The mixture was stirred at room temperature for 3 days, and then sodium carbonate (0.32 g, 3 mmol) and methanol (5 mL) were added. The mixture was stirred for 20 minutes, then filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (methanol/ethyl acetate=1:10) to give the titled compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10-1.90 (m, 6H), 2.10 (m, 1H), 2.70-3.15 (m, 5H), 4.40-4.60 (m, 1H), 7.30 (d, 2H, J=7 Hz), 7.63 (m, 4H), 7.76 (br s, 1H), 7.90 (m, 1H), 10.85 (br s, 1H); MS (ESI) m/z 454 (M+H)+.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 3 days
  2. stirringThe mixture was stirred for 20 minutes
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (methanol/ethyl acetate=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-8d7ad637540e4fb1a54cd51755d0040e
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741899B2

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