5-Aminoimidazole-4-carboxamide → Temozolomide

HRID 2381889

Reaction equation

HRID 2381889 reaction equation
NC1NC=NC=1C(N)=O.[N+:10](=[C:12]1[NH:16][CH2:15][N:14]=[C:13]1[C:17]([NH2:19])=[O:18])=[N-:11].[CH3:20][N:21]=[C:22]=[O:23]>ClCCl>[CH3:20][N:21]1[N:11]=[N:10][C:12]2[N:16]([CH:15]=[N:14][C:13]=2[C:17]([NH2:19])=[O:18])[C:22]1=[O:23]

Participants

5

Reactant 3

HCID 96795-Aminoimidazole-4-carboxamideHCID 12228Methyl IsocyanateHCID 1363774465-diazo-1H-imidazole-4-carboxamide

Product 1

HCID 5394Temozolomide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Med. Chem. 1984, 27, 196-201 describes a process wherein 5-amino-1H-imidazole-4-carboxamide is converted into 5-diazo-1H-imidazole-4-carboxamide, which is then cyclised with methylisocyanate in dichloromethane to provide a high yield of temozolomide.

Sources & evidence

ORD record
ord-921888acf71f4518ac900a0a05f2b570
Source dataset
uspto-grants-2012_09
Patent number
US08258294B2

Linked notes

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