Diisopropylamine → 2-(4-((2,6-Dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)amino)pentyl)isoindoline-1,3-dione

HRID 2290657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2290657
[NH2:1][C:2]1[CH:3]=[C:4]([O:26][CH3:27])[C:5]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[C:7]2[CH3:14].C(NC(C)C)(C)C.I[CH:36]([CH3:51])[CH2:37][CH2:38][CH2:39][N:40]1[C:44](=[O:45])[C:43]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]2[C:41]1=[O:50]>CC#N.O>[CH3:13][O:12][C:9]1[CH:8]=[C:7]([CH3:14])[C:6]2[C:11](=[C:2]([NH:1][CH:36]([CH3:51])[CH2:37][CH2:38][CH2:39][N:40]3[C:44](=[O:45])[C:43]4=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]4[C:41]3=[O:50])[CH:3]=[C:4]([O:26][CH3:27])[C:5]=2[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)[N:10]=1

Komponenten

6

Edukt 3

HCID 7912Diisopropylamine3×HCID 98211042,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-amineHCID 123682034-Iodo-1-phthalimido-pentane3×

Produkt 1

HCID 137459272-(4-((2,6-Dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)amino)pentyl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 8-amino-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline (8.0 g, 21.2 mmol), diisopropylamine (2.14 g, 21.2 mmol) and 4-iodo-1-phthalimidopentane (IPP) (7.26 g, 21.2 mmol) in CH3CN (40 mL) was refluxed for 24 hours after which time additional diisopropylamine (2.14 g, 21.2 mmol) and IPP (7.26 g, 21.2 mmol) were added. After refluxing a further 24 hours, more diisopropylamine (1.07 g, 10.6 mmol) and IPP (3.63 g, 10.6 mmol) were added and refluxing was continued a further 24 hours. The cooled mixture was diluted with H2O (20 mL) and stirred in an ice bath until crystallization was complete. Filtration and recrystallization from IPA gave 8.4 g (67%) of 1st crop title compound, mp 120°-124° C. Further recrystallization raised the mp to 121°-124° C.

Aufarbeitung

  1. additionwere added
  2. temperatureAfter refluxing a further 24 hours
  3. temperaturerefluxing
  4. filtrationFiltration and recrystallization from IPA

Quellen und Nachweise

ORD-Eintrag
ord-dae485710f714fd2b1eabc4ca236d563
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04617394

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