IP Library › Patent Application 16462207
Patent Application
App. No. 16/462,207

4-((6-(2-(2,4-DIFLUOROPHENYL)-1,1-DIFLUORO-2-HYDROXY-3-(5-MERCAPTO-1H-1,2,4-TRIAZOL-1-YL)PROPYL)PYRIDIN-3-YL)OXY)BENZONITRILE AND PROCESSES OF PREPARATION

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Quick Facts
Patent No.
US None
App. No.
16/462,207
Abstract

Provided herein is a process for the preparation of 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1H-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile.

Claims (19)

1 . A method of making a compound of Formula I comprising:

contacting a compound of Formula II

with a sulfur reagent.

2 . The method of claim 1 wherein the sulfur reagent may be selected from the group including phosphorus pentasulfide, Lawesson's reagent, and hydrogen sulfide, or derivatives of hydrogen sulfide.

3 . The method of claim 1 wherein the sulfur reagent is phosphorus pentasulfide.

4 . The method of claim 1 further comprising a solvent selected from the group including acetonitrile, ethyl acetate, toluene, THF, dioxane, ethanol, and mixtures thereof.

5 . The method of claim 1 wherein the contacting is carried out between about 25° C. and about 150° C.

6 . The method of claim 1 wherein the contacting is carried out between about 50° C. and about 100° C.

7 . The method of claim 1 , further comprising the step of contacting a compound of Formula III

with an organic carbamate, 1,1-dimethoxy-N,N-dimethylmethanamine, and an acid to produce the compound of Formula II.

8 . The method of claim 7 further comprising a pre-heating step whereby a mixture of the organic carbamate, the 1,1-dimethoxy-N,N-dimethylmethanamine and a solvent are combined and pre-heated prior to addition of the acid and the compound of Formula III.

9 . The method of claim 7 further comprising a solvent selected from the group including toluene, a xylene, ethyl acetate, THF, acetonitrile, and mixtures thereof.

10 . The method of claim 7 wherein the acid is acetic acid.

11 . The method of claim 7 wherein the alkyl carbamate is ethyl carbamate.

12 . The method of claim 7 wherein the contacting is carried out from about 25° C. to about 150° C.

13 . The method of claim 7 wherein the contacting is carried out from about 50° C. to about 100° C.

14 . The method of claim 8 wherein the pre-heating is conducted at about 50° C. to about 150° C.

15 . The method of claim 8 wherein the pre-heating is conducted at about 50° C. to about 100° C.

16 . A compound consisting of: