2-(1-Piperidyl)ethoxyamine dihydrochloride → 4-(3-Chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(1-piperidyl)ethoxyimino)quinazoline

HRID 220112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220112
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25](C=O)[CH:26]=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.Cl.Cl.[N:32]1([CH2:38][CH2:39][O:40][NH2:41])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>O1CCCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[CH2:26][C:25](=[N:41][O:40][CH2:39][CH2:38][N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)[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

6

Edukt 2

HCID 212756742-(1-Piperidyl)ethoxyamine dihydrochlorideHCID 577336564-(3-Chloro-4-(3-fluorobenzyloxy)phenylamino) 6-formylquinazoline

Produkt 1

HCID 866309154-(3-Chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(1-piperidyl)ethoxyimino)quinazolineAusbeute 20,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a mixture of tetrahydrofuran (2 ml) and water (0.1 ml) were dissolved 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-formylquinazoline (IV-1, 50 mg) and 2-(1-piperidyl)ethoxyamine dihydrochloride (36.5 mg), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed sequentially with aqueous saturated sodium bicarbonate solution, and aqueous sodium chloride solution, and dried over magnesium sulfate. After concentration, the residue was purified by chromatography (eluting with hexane:ethyl acetate=2:3) using an amino column, and further re-purified by thin layer chromatography to obtain 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(1-piperidyl)ethoxyimino)quinazoline (V-1, 13 mg).

Aufarbeitung

  1. washwashed sequentially with aqueous saturated sodium bicarbonate solution, and aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationAfter concentration
  4. customthe residue was purified by chromatography (eluting with hexane:ethyl acetate=2:3)
  5. customfurther re-purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-48c75bf2b9d8478e9c8c418bf796efd7
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202879B2

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