Pentanoic Acid → HCID 178447239, compound

Participants

Reaction Steps

A mixture of 1.02 g of valeric acid, 4.50 g of 4-amino-1,2-dihydro-2-oxo-3-(4-(2-(1H-5-tetrazolyl)-3-thienyl)benzylamino)-1-(N,N-dimethylcarbamoylmethyl)pyridine [obtainable by reaction of 3-amino-4-benzylamino-1,2-dihydro-2-oxo-1-(N,N-dimethylcarbamoylmethyl)pyridin with IIa to give 4-benzylamino-3-oxo-1-(N,N-dimethylcarbamoylmethyl)pyridine, reaction with trimethyltin azide to give 4-benzylamino-1,2-dihydro-2-oxo-3-(4-(2-(1H-5-tetrazolyl)-3-thienyl)benzylamino)-1-(N,N-dimethylcarbamoylmethyl)pyridine and hydrogenolytic removal of the benzyl group] and 50 g of polyphosphoric acid is heated for 5 hours at 140°. 4-Amino-1,2-dihydro-2-oxo-3-(N-4-(2-(1H-5-tetrazolyl)-3-thienyl)benzyl-N-valerylamino)-1-(N,N-dimethylcarbamoylmethyl)pyridine and 1,2-dihydro-2-oxo-3-(4-(2-(1H-5-tetrazolyl)-3-thienylbenzylamino)-1-(N,N-dimethylcarbamoylmethyl)-4-valerylaminopyridine are formed in situ as intermediates. The mixture is cooled, poured onto ice, rendered alkaline with sodium hydroxide solution and worked up in the conventional manner, and gives 2-butyl-3-(4-(2-(1H-5 -tetrazolyl)-3-thienyl)benzyl-4,5-dihydro-4-oxo-5-(N,N-dimethylcarbamoylmethyl)-3H-IP.

Provenance & Evidence