Trifluoroacetic acid → 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(N-ethylamino)ethyloxyimino)quinazoline

HRID 220114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220114
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[CH2:26][C:25](=[N:28][O:29][CH2:30][CH2:31][N:32](C(OC(C)(C)C)=O)[CH2:33][CH3:34])[CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[CH2:26][C:25](=[N:28][O:29][CH2:30][CH2:31][NH:32][CH2:33][CH3:34])[CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 866309164-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(N-(t-butoxycarbonyl)-N-ethylamino)ethyloxyimino)quinazoline

Produkt 1

HCID 866309184-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(N-ethylamino)ethyloxyimino)quinazolineAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In chloroform (1.8 ml) was dissolved 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(N-(t-butoxycarbonyl)-N-ethylamino)ethyloxyimino)quinazoline (V-16, 54 mg), and trifluoroacetic acid (1.8 ml) was added, followed by stirring at room temperature for 1 hour. After completion of the reaction, the reaction mixture was concentrated, and diluted with ethyl acetate. The mixture was sequentially washed with aqueous saturated sodium bicarbonate solution, water, and aqueous sodium chlorite solution, and dried over magnesium sulfate. After concentration, the crystalline residue was washed with a mixture of dichloromethane-hexane (1:4) to obtain 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(N-ethylamino)ethyloxyimino)quinazoline (V-17, 28 mg) as a white solid.

Aufarbeitung

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. additiondiluted with ethyl acetate
  5. washThe mixture was sequentially washed with aqueous saturated sodium bicarbonate solution, water, and aqueous sodium chlorite solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentration
  8. washthe crystalline residue was washed with a mixture of dichloromethane-hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-20d1021c1f3d427289d1344a0a0d8d99
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202879B2

Notizen zur Reaktion

Wird geladen…