Hydrazine → HCID 178510603, compound
Reaction equation
N1C=NC(C(OC)=O)=N1.[C:10]([C:12]1[N:16]=[CH:15][NH:14][N:13]=1)#[N:11].CC1N=CNN=1.N#CC#N.NN>>[C:10]([C:12]1[N:16]=[CH:15][NH:14][N:13]=1)#[N:11].[C:10]([C:12]([NH:13][NH2:14])=[NH:16])#[N:11]Participants
Procedure
Methyl 1,2,4-triazole-3-carboxylate and 3-cyano-1,2,4-triazole are precursors in alternative synthetic routes to 1,2,4-triazole nucleosides of the invention. The former compound can be conventionally prepared by oxidation of 3-methyl-1,2,4-triazole followed by esterification of the resulting acid according to the procedure of Cipens and Grinsteins' Latvijas PSR Zinatnu Akad. Vestis., Kim. Ser. (1965) (2) 204-08 (see C.A. 63, 13243, 1965). 3-cyano-1,2,4-triazole is prepared by a multi-step synthesis reported by Cipens et al., supra, or more conveniently, by the addition reaction of cyanogen and hydrazine to form 1-cyanoformimidic acid hydrazide, followed by acid-catalyzed ring closure in triethylorthoformate to the 3-cyano compound. By one route, the trimethylsilyl derivative of the methyl 1,2,4-triazole-3-carboxylate is formed in quantitative yield by reaction with hexamethyldisilazane under reflux and reacted with an appropriate O-acylated halo sugar GX to form, for example, a mixture of O-benzoylated 1-(β -D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyle ester and 5-carboxylic acid methyl ester, i.e.: ##STR4## wherein Bz is benzoyl. The 3-carboxylic acid methyl ester is separated by fractional crystallization or, preferably, by column chromatography over silica gel. Debenzoylation and aminolysis gives the 1-(β -D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.
Sources & evidence
- ORD record
- ord-4925c1921adb456bb267c2469209bae1
- Source dataset
- uspto-grants-1978_11
- Patent number
- USRE029835
Reaction notes
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