Butylamine → n-Butyl-4-(2-oxo-4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzenesulfonamide

HRID 11801

Reaktionsgleichung

Reaktionsgleichung von HRID 11801
[O:1]=[C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:8]=2)[NH:3]1.[CH2:27]([NH2:31])[CH2:28][CH2:29][CH3:30]>>[CH2:27]([NH:31][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[CH:11]=[C:10]3[C:12]([F:15])([F:14])[F:13])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[CH2:28][CH2:29][CH3:30]

Komponenten

3

Edukt 2

HCID 8007ButylamineHCID 219767284-(2-Oxo-4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzenesulfonyl chloride

Produkt 1

HCID 11362641n-Butyl-4-(2-oxo-4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzenesulfonamideAusbeute 91,2 %

Versuchsvorschrift

4-(2-oxo-4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzenesulfonyl chloride (Preparation 1, 26 mg, 65 μmol) was reacted with an excess of n-BuNH2 (190 mg, 2600 μmol) by the same procedure used for Example 1. After reaction, the solvents were evaporated off under reduced pressure & the residue partitioned between EtOAc (10 mL) & 2 M HCl (3 mL). The organic phase was washed with H2O (2 mL), 1 M NaOH (3 mL), & brine (2 mL), before being dried (MgSO4). Filtration & solvent evaporation furnished the title compound (26 mg, 84%): δH ((CD3)2SO)=0.75 (t, 3H), 1.20–1.35 (m, 4H), 2.65 (m, 2H), 4.15 (s, 2H), 6.95 (s, 1H), 7.35–7.55 (m, 5H), 7.70 (d, 2H); m/z (ES+)=480.2 [M+H+MeCN]+.

Aufarbeitung

  1. customAfter reaction
  2. customthe solvents were evaporated off under reduced pressure
  3. customthe residue partitioned between EtOAc (10 mL) & 2 M HCl (3 mL)
  4. washThe organic phase was washed with H2O (2 mL), 1 M NaOH (3 mL), & brine (2 mL)
  5. dry with materialbefore being dried (MgSO4)
  6. filtrationFiltration & solvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-c0c4244a11c84b8bb0979a414d3e20be
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098340B2

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