1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → (S)-N-(alpha-ethylbenzyl)-2-phenyl-3-(2-phthalimidoethoxy)quinoline-4-carboxamide

HRID 651056

Reaktionsgleichung

Reaktionsgleichung von HRID 651056
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[OH:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].Br[CH2:31][CH2:32][N:33]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:31][CH2:32][N:33]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-3×HCID 11430Potassium CarbonateHCID 5311424Talnetant

Produkt 1

HCID 11800901(S)-N-(alpha-ethylbenzyl)-2-phenyl-3-(2-phthalimidoethoxy)quinoline-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1.90 g (5.0 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (product of Description 1) were dissolved in 20 ml of THF. 3.80 g (14.9 mmol) of N-(2-bromoethyl)phthalimide dissolved in 15 ml of THF, 2.00 g (14.5 mmol) of K2CO3 and 0.25 g of KI were added and the suspension was stirred at room temperature for 2.5 hours and then refluxed for 2 hours. Additional 1.90 g (7.4 mmol) of N-(2-bromoethyl)phthalimide and a catalytic amount of KI were added and the reaction refluxed for 3.5 hours; additional 0.50 g (2.0 mmol) of N-(2-bromoethyl)phthalimide and a catalytic amount of KI were added and the reaction refluxed for 5 hours.

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. temperaturethe reaction refluxed for 3.5 hours
  3. temperaturethe reaction refluxed for 5 hours

Quellen und Nachweise

ORD-Eintrag
ord-02f654b91404405688046646914f2fab
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277862B1

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