Temozolomide → 5-Amino-N4-(1,1-dimethylethyl)-N1-methyl-1H-imidazole-1,4-dicarboxamide

HRID 1433125

Reaktionsgleichung

Reaktionsgleichung von HRID 1433125
[CH3:1][N:2]1N=[N:10][C:9]2[N:5]([CH:6]=[N:7][C:8]=2[C:12]([NH2:14])=[O:13])[C:3]1=[O:4].C(C(N=C(C1C=CC=CC=1)C1C=CC=CC=1)C(N[C:21]([CH3:24])([CH3:23])[CH3:22])=O)#N.Cl.NC(C#N)C(NC(C)(C)C)=O>>[NH2:10][C:9]1[N:5]([C:3]([NH:2][CH3:1])=[O:4])[CH:6]=[N:7][C:8]=1[C:12]([NH:14][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:13]

Komponenten

4

Edukt 3

HCID 5394TemozolomideHCID 11393010HCID 11393010, VerbindungHCID 220154222-amino-2-cyano-N-(1,1-dimethylethyl)-acetamide hydrochloride

Produkt 1

HCID 112534275-Amino-N4-(1,1-dimethylethyl)-N1-methyl-1H-imidazole-1,4-dicarboxamide

Versuchsvorschrift

Another process for preparing Temozolomide is described in U.S. patent application having the Publication No. 2002/0095036 (see Scheme 4 below). In this process, the imine (V) is converted to 2-cyano-N-(1,1-dimethylethyl)-2-[(diphenyl-methylene)amino]-acetamide, which is converted to 2-amino-2-cyano-N-(1,1-dimethyl-ethyl)-acetamide hydrochloride. The latter is reacted with compound (VI) to obtain 5-amino-N4-(1,1-dimethylethyl)-N1-methyl-1H-imidazole-1,4-dicarboxamide, which is converted to 3,4-dihydro-N-(1,1-dimethylethyl)-3-methyl-imidazo-[5,1-d]-1,2,3,5-tetrazine-8-carboxamide (tert-butyl-Temozolomide), which yields Temozolomide under acidic treatment with concentrated sulfuric acid.

Quellen und Nachweise

ORD-Eintrag
ord-30d9ac5cf4b84f348e83266310595dc2
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612202B2

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