Trifluoroacetic acid → Anticancer agent 95

HRID 547457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547457
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:26]([C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=1)[CH2:27][CH2:28][CH2:29][NH:30]C(=O)OC(C)(C)C)[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:30][CH2:29][CH2:28][CH2:27][N:26]([CH:20]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=1)[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:38](=[O:46])[C:39]1[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 58378188Tert-butyl 3-[[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl](4-methylbenzoyl)amino]propylcarbamate

Produkt 1

HCID 11272772Anticancer agent 95

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 3-[[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl](4-methylbenzoyl)amino]propylcarbamate (500 mg), was added 20% solution of trifluoroacetic acid in methylene chloride at room temperature. The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The crude product was purified by flash chromatography to give N-(3-aminopropyl)-N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]-4-methylbenzanide (336 mg) as a white solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customThe crude product was purified by flash chromatography
  3. customto give N-(3-aminopropyl)-N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]-4-methylbenzanide (336 mg) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-0421b31656174d1ba9643489b3f5a9d6
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939539B2

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