IP Library › Patent Application 16462203
Patent Application
App. No. 16/462,203

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.
16/462,203
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 (17)

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

contacting a compound of Formula II

with formaldehyde or a source of formaldehyde, a thiocyanate salt and an oxidant.

2 . The method of claim 1 , wherein the thiocyanate salt is selected from the group including potassium thiocyanate, sodium thiocyanate, and ammonium thiocyanate.

3 . The method of claim 1 , wherein the oxidant comprises an iron (III) compound, sodium hypochlorite, manganese dioxide, or hydrogen peroxide.

4 . The method of claim 3 , wherein the iron (III) compound is iron (III) chloride, iron (III) bromide, or iron (III) acetylacetonate.

5 . The method of claim 3 , wherein the iron (III) compound is iron (III) chloride.

6 . The method of claim 1 further comprising a solvent selected from the group including ethyl acetate, tetrahydrofuran, 2-MeTHF, acetonitrile, N,N-dimethylformamide, N-methyl-2-pyrrolidone, methyl t-butyl ether, ethanol, and mixtures thereof.

7 . The method of claim 1 further comprising an acid selected from the group including acetic acid, sodium hydrogen sulfate, and potassium hydrogen sulfate.

8 . The method of claim 1 wherein the contacting is carried out between about 0° C. and about 100° C.

9 . The method of claim 1 wherein the contacting is carried out between about 10° C. and about 50° C.

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

with hydrazine to produce the compound of Formula II.

11 . The method of claim 10 further comprising a solvent selected from methanol, ethanol, 1-propanol, 2-propanol, THF, acetonitrile, DMSO, NMP, and mixtures thereof.

12 . The method of claim 10 wherein the contacting is carried out between about 25° C. and about 100° C.

13 . The method of claim 10 wherein the contacting is carried out between about 40° C. and about 80° C.

14 . A compound selected from the group consisting of: