5-Amino-1,2-dihydroquinolin-2-one → 5-{[4,4-Dimethyl-6-fluoro-2-hydroxy-5-methoxy-2-trifluoromethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-quinolin-2(1H)-one

HRID 1869373

Reaktionsgleichung

Reaktionsgleichung von HRID 1869373
[F:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.[NH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27](=[O:33])[NH:28]2>[Ti](Cl)(Cl)(Cl)Cl>[CH3:19][C:8]1([CH3:18])[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[O:20][CH3:21])[CH:11]([NH:22][C:23]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:24]=2[CH:25]=[CH:26][C:27](=[O:33])[NH:28]3)[C:10]([OH:17])([C:13]([F:16])([F:14])[F:15])[CH2:9]1

Komponenten

4

Edukt 2

HCID 157190785-Amino-1,2-dihydroquinolin-2-oneHCID 179890864-(3-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Produkt 1

HCID 686804845-{[4,4-Dimethyl-6-fluoro-2-hydroxy-5-methoxy-2-trifluoromethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-quinolin-2(1H)-oneAusbeute 2,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24193Titanium TetrachlorideKatalysator

Versuchsvorschrift

Analogously to Example 3, the corresponding imine is produced starting from 500 mg of 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal and 260 mg of 5-aminoquinolin-2(1H)-one. By reaction of 80 mg of the imine with 0.5 ml of titanium tetrachloride (1 M in dichloromethane), 20 mg of the title compound is obtained.

Quellen und Nachweise

ORD-Eintrag
ord-f438499948644e70b8a2010d2ae4990c
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638515B2

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