Isopropylamine → n-Isopropyl-4-(2-oxo4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzenesulfonamide

HRID 11800

Reaktionsgleichung

Reaktionsgleichung von HRID 11800
[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.[CH:27]([NH2:30])([CH3:29])[CH3:28].CCOC(C)=O>C(Cl)Cl>[CH:27]([NH:30][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])([CH3:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 6363IsopropylamineHCID 8857Ethyl AcetateHCID 219767284-(2-Oxo-4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzenesulfonyl chloride

Produkt 1

HCID 11487073n-Isopropyl-4-(2-oxo4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzenesulfonamideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A stirred solution of 4-(2-oxo4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)-benzenesulfonyl chloride (Preparation 1, 17 mg, 42 μmol) in anhydrous CH2Cl2 (0.5 mL) was treated dropwise with an excess of i-PrNH2 (145 μL, 1680 μmol). After stirring at 20° C. for 10 min, the reaction mixture was submitted to column chromatography (EtOAc) to furnish the title compound (8 mg, 45%): δH (CD3OD)=1.00 (d, 6H), 3.35 (sept, 1H), 4.20 (s, 2H), 7.00 (s, 1H), 7.15–7.20 (m, 3H), 7.50 (dd, 1H), 7.60 (d, 1H), 7.80 (d, 2H); m/z (ES+)=466.1 [M+H+MeCN]+.

Quellen und Nachweise

ORD-Eintrag
ord-9d9accae0f0f4ed7971d30ee908f5890
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098340B2

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