Cyanogen Bromide → Quinazolin-2-amine

HRID 1935669

Reaktionsgleichung

Reaktionsgleichung von HRID 1935669
[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>>[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

5

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

Versuchsvorschrift

Commercially, as discussed in U.S. Pat. No. 5,801,245 and as shown in FIG. 1, Anagrelide has been prepared as the hydrochloride monohydrate (compound IV) from the intermediate, ethyl N-(6-amino-2,3-dichlorobenzyl)glycine (compound I) by reaction with cyanogen bromide in hot alcohol solution, or, preferentially, by reaction with cyanogen bromide in an aprotic solvent 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-8a2f6eca11644f39bb21afa3dcb925e5
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06388073B1

Verknüpfte Notizen

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