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US 8,895,747 B2Granted
Method and substances for preparation of N-substituted pyridinium compounds
AssigneeRoche Diagnostics Operations, Inc.
InventorsDieter Heindl, Heribert Maerz, Axel Schmidt
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Abstract
Methods for the synthesis of N-substituted pyridinium compounds by using an N-heteroaryl substituted pyridinium salt (Zincke salt) and reacting it with a nucleophilic amine are provided. Novel purine-substituted pyridyl compounds, which may be useful reagents in the above reaction, are also disclosed.
Claims12
A method for synthesis of an N-substituted pyridinium compound comprising the steps of:
- a) providing a Zincke salt according to any of following Formulas (IV)-(VII) and having at least one counter ion, selected from the group consisting of:
- Cl, Br, Tosylate, Mesylate, and Triflate:
- wherein
- X is O or S,
- R1 is methyl, ethyl, O-methyl, O-ethyl, NH2, N-dimethyl, N-diethyl, and
- R2 is NH2;
- wherein
- X is O or S,
- R1 is methyl, ethyl, O-methyl, O-ethyl, NH2, N-dimethyl, N-diethyl, and
- R2 is NH2 or Cl;
- wherein
- X is O or S,
- R1 is methyl, ethyl, O-methyl, O-ethyl, NH2, N-dimethyl, N-diethyl, and
- R2 and R3 independently are O—C1-C3 alkyl or NH2;
- wherein
- X is O or S,
- R1 is methyl, ethyl, O-methyl, O-ethyl, NH2, N-dimethyl, N-diethyl, and
- R2 and R3 independently are O—C1-C3 alkyl and R7=H or Cl;
- b) reacting the Zincke salt of step (a) with a primary amine of Formula II:
- wherein
- the primary amine of Formula II is selected from the group consisting of:
- an alkyl amine, an alkyenyl amine, a heterocycloalkyl amine, an aryl amine, a heteroaryl amine, an amino alcohol, an amino acid, a furanoxylamine, or a cyclopentylamine,
- c) obtaining, an N-substituted pyridinium compound of Formula III:
- having a counter ion,
- wherein X is O or S,
- R1, is methyl, ethyl, O-methyl, O-ethyl, NH2, N-dimethyl, N-diethyl;
- and
- R6 is selected from the group consisting of:
- alkyl, alkyenyl, heterocycloalkyl, aryl, heteroaryl, hydroxyalkyl, carboxylic acid, a furanoxyl, or cyclopentyl.
26 more elements
Dependencies are inferred from the claim text.