Cyanogen Bromide → Quinazolin-2-amine

HRID 2178727

Reaktionsgleichung

Reaktionsgleichung von HRID 2178727
[CH:1]1[C:6]2[N:7]=[C:8]3[N:13]([CH2:14][C:5]=2[C:4](Cl)=[C:3](Cl)[CH:2]=1)CC(=O)[NH:9]3.O.Cl.C(N(CC1C(N)=CC=C(Cl)C=1Cl)CC(O)=O)C.N#CBr>C1(C)C=CC=CC=1>[NH:9]=[C:8]1[N:13]=[CH:14][C:5]2[C:6](=[CH:1][CH:2]=[CH:3][CH:4]=2)[NH:7]1

Komponenten

6

Edukt 4

HCID 10476Cyanogen Bromide2×HCID 21885828Hydrate;hydrochloride2×HCID 67080112ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine2×HCID 135409400Anagrelide

Produkt 1

HCID 178508286Quinazolin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Commercially, as discussed in U.S. Pat. No. 5,801,245, and as shown in Scheme 1 below, anagrelide has been prepared as the hydrochloride monohydrate (compound IV) from the intermediate, ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine (compound I), either by reaction with cyanogen bromide in hot alcoholic solution, or, preferentially, by reaction with cyanogen bromide in an aprotic solvent such as toluene to give the iminoquinazoline intermediate (compound II), which is isolated and then reacted with a base in a hot solution of alcohol to form anagrelide base (compound III).

Quellen und Nachweise

ORD-Eintrag
ord-1ab8ad0e7f384b0191570b857b431b25
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067944B2

Verknüpfte Notizen

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