3-(Trifluoromethyl)aniline → 3-(octahydro-2H-pyrido[1,2-a]pyrazin-2-ylcarbonyl)-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide

HRID 400513

Reaktionsgleichung

Reaktionsgleichung von HRID 400513
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][CH2:23][CH:15]12.C(=O)([O-])[O-].[Na+].[Na+].[F:30][C:31]([F:40])([F:39])[C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35]>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][CH:38]=[C:32]([C:31]([F:30])([F:39])[F:40])[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][CH2:23][CH:15]12

Komponenten

7

Edukt 4

HCID 73753-(Trifluoromethyl)anilineHCID 10340Sodium Carbonate2×HCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 2876391(+-)-1,4-Diazabicyclo[4.4.0]decane

Produkt 1

HCID 468518103-(octahydro-2H-pyrido[1,2-a]pyrazin-2-ylcarbonyl)-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 3-(chlorosulfonyl)benzoyl chloride (0.36 g 1.5 mmol) in anhydrous dichloromethane (50 mL) was added octahydro-1H-pyrido[1,2-a]pyrazine (0.21 g, 1.5 mmol) in dichloromethane (4 mL) slowly over 10 minutes at room temperature. Then sodium carbonate (0.32 g, 3 mmol) was added. The mixture was stirred at room temperature for 5 hours. Then 3-(trifluoromethyl)aniline (2.9 g, 18 mmol) was added. The mixture was stirred at room temperature for 5 days, 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. 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 1.00-1.27 (m, 3H), 1.42-2.10 (m, 7H), 2.70-3.40 (m, 4H), 4.25-4.40 (m, 1H), 7.40 (m, 3H), 7.50 (m, 1H), 7.70 (m, 3H), 7.85 (m, 1H), 10.80 (br s, 1H); MS (ESI) m/z 468 (M+H)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bd982559a8a54c43bdf7da275ecf6cd0
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741899B2

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