Patent ID: 9102654
Filing Date: 2015-08-11
Classification: A01N,C07D

Abstract:
1. A process comprising: (a) reacting 3-hydrazinopyridine dihydrochloride with glyoxylic acid to yield (E)-2-(2-(pyridin-3-yl)hydrazono)acetic acid (6a) (b) reacting (E)-2-(2-(pyridin-3-yl)hydrazono)acetic acid (6a) with acrylonitrile and a source of chlorine, in the presence of a base, to yield 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carbonitrile (6b) (c) dehydrocyanating 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carbonitrile (6b), in the presence of a base, to yield 3-(3-chloro-1H-pyrazol-1-yl)pyridine (5b) (d) nitrating 3-(3-chloro-1H-pyrazol-1-yl)pyridine (5b) with nitric acid (HNO (e) reducing 3-(3-chloro-4-nitro-1H-pyrazol-1-yl)pyridine (5c) to yield 3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine (5d) (f) acylating 3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine (5d) with acetic anhydride, in the presence of an inorganic base, to yield N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide (1c) (g) reducing N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide (1c) to yield 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-amine (1d) and (h) reacting 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-amine (1d) with an activated carbonyl thioether of formula X wherein R X