- Preparation of 2-(2-thienyl) ethylamine and synthesis of thieno [3,2-C] pyridine derivatives therefrom
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Compounds of the formulae:and wherein:, R1, R2, R3 and R4 are independently hydrogen, lower alkyl of one to six carbon atoms, aryl or substituted aryl;, are advantageously converted to isocyanurate compounds, 2-(2-thienyl)ethylamine compounds and thieno[3,2-c]pyridine derivatives and the pharmaceutically acceptable salts thereof, particularly ticlopidine hydrochloride.
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- Carbamate salts of 2-(2'-thienyl)alkylamines
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The carbamate salt of 2-(2'-thienyl)-alkylamines and particularly the ethylamine and its method of synthesis are disclosed. The carbamate salt of 2-(2'-thienyl)ethylamine is a stable, easily transportable crystalline material that can be converted to 2-(2'-thienyl)ethylamine, a useful intermediate in the synthesis of 5[(2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno-[3,2-c]pyridine hydrochloride, also known as ticlopidine hydrochloride. The synthesis is carried out by reacting an amine of formula (I): STR1 with CO2 in a hydrocarbon solvent to obtain the carbamate salt of formula II: STR2
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- 2-(2-nitrovinyl)thiophene reduction and synthesis of thieno[3,2-c]pyridine derivatives
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An improved process for the reduction of 2-(2-nitrovinyl)thiophene to form 2-(2-thienyl)ethylamine employs a boron-containing reducing agent, preferably diborane. The 2-(2-thienyl)ethylamine produced by this process is advantageously converted to ticlopidine.
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- Synthesis of thienopyridine and furopyridine derivatives of therapeutic interest
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5-Benzyl-4,5,6,7-tetrahydrothieno [3,2-c] pyridines and analogous furopyridines were synthesized by NaBH4 reduction of the corresponding quaternary ammonium salts (method A). In the former series, the same derivatives were obtained by condensing benzyl halides with tetrahydrothienopyridine (method B).
- Maffrand,Eloy
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p. 483 - 486
(2007/10/05)
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