Cyanogen Bromide → Quinazolin-2-amine

HRID 41350

Reaktionsgleichung

Reaktionsgleichung von HRID 41350
[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 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) 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-16c12e29c27c4e31ace7baeccc73080c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530651B2

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