Methanol → N-{4-[(6,7-Dimethoxy-4-quinazolinyl)-oxy]phenyl}-N'-(2-propynyl)urea

HRID 1375824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375824
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.Cl.[CH2:36]([NH2:39])[C:37]#[CH:38].CO>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:27]([NH:39][CH2:36][C:37]#[CH:38])=[O:33])=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 94429TriphosgeneHCID 11205720Prop-2-ynylamine hydrochlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Produkt 1

HCID 22667127N-{4-[(6,7-Dimethoxy-4-quinazolinyl)-oxy]phenyl}-N'-(2-propynyl)ureaAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.2 ml), and a solution of triphosgene (50 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, propargylamine hydrochloride (31 mg) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Methanol was added to the reaction solution, and the mixture was purified by HPLC by development with chloroform/methanol to give 26 mg (yield 41%) of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. customthe mixture was purified by HPLC by development with chloroform/methanol

Quellen und Nachweise

ORD-Eintrag
ord-ee8ff045aa354218b6e748cf7fac732d
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169789B2

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