Granted Patent B2

US 12,552,797 · App. 17/780,570 · Granted Feb 17, 2026

Inventors: Gabriel Martinez Botella (Wayland, MA); Andrew Mark Griffin (L'lle Bizard, CA)

Assignee: Praxis Precision Medicines, Inc.

C07D487/04A61K9/14A61P25/06

Abstract

Claims (19)

1 . A process for making Compound 1 of the following formula:

wherein the process comprises the following steps:

(i) contacting a solution of 2,2,2-trifluoroethanol with 5-bromo-2,3-difluoropyridine, thereby providing a compound of formula (II):

(ii) contacting the compound of formula (II) provided in step (i) above with a palladium catalyst and bis(pinacoloto)diboron, thereby providing a compound of formula (III):

(iii) contacting the compound of formula (III) provided in step (ii) above with a palladium catalyst and 2-bromo-5-chloropyrazine, thereby providing a compound of formula (IV):

(iv) contacting the compound of formula (IV) provided in step (iii) above with hydrazine, thereby providing a compound of formula (V):

(v) contacting the compound of formula (V) provided in step (iv) above with 2-bromo-2,2-difluoroacetyl chloride, thereby providing a compound of formula (VI):

(vi) contacting the compound of formula (VI) provided in step (v) above with an acid, thereby providing a compound of formula (VII):

and

(vii) contacting the compound of formula (VII) provided in step (vi) above with a silver catalyst and ethanol, thereby providing Compound 1 above.

2 . The process of claim 1 , wherein the silver catalyst in step (vii) is silver tetrafluoroborate.

3 . The process of claim 1 , wherein the acid in step (vi) is p-toluenesulfonic acid.

4 . The process of claim 1 , wherein the palladium catalyst in step (ii) is [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

5 . The process of claim 1 , wherein the palladium catalyst in step (iii) is [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

6 . The process of claim 1 , wherein:

(a) the palladium catalyst in step (ii) is [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride;

(b) the palladium catalyst in step (iii) is [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride;

(c) the acid in step (vi) is p-toluenesulfonic acid; and

(d) the silver catalyst in step (vii) is silver tetrafluoroborate.

Assignments (1)

Continuity (8)

References Cited (214)