	US 12,441,681 B2
	Synthesis of sulfonamide intermediates
Neil Fred Langille, Sudbury, MA (US); Jason S. Tedrow, Salem, MA (US); Jonathan Vinh-Phu Truong, Thousand Oaks, CA (US); Robert Ronald Milburn, Belmont, CA (US); and Alessandro Arena, Vicenza (IT)
Assigned to AMGEN INC., Thousand Oaks, CA (US); and F.I.S.—FABBRICA ITALIANA SINTETICI SPA, Vicenza (IT)
Appl. No. 17/923,015
Filed by AMGEN INC., Thousand Oaks, CA (US)
PCT Filed Apr. 28, 2021, PCT No. PCT/US2021/029523 § 371(c)(1), (2) Date Nov. 3, 2022, PCT Pub. No. WO2021/225833, PCT Pub. Date Nov. 11, 2021.
Claims priority of provisional application 63/020,951, filed on May 6, 2020.
Prior Publication US 2023/0357137 A1, Nov. 9, 2023
Int. Cl. C07C 303/36 (2006.01); C07C 29/62 (2006.01); C07C 67/08 (2006.01); C07C 303/28 (2006.01); C07D 213/70 (2006.01); C07D 213/71 (2006.01); C07D 301/24 (2006.01); C07D 513/06 (2006.01); C07D 519/00 (2006.01)

CPC C07C 303/36 (2013.01) [C07C 29/62 (2013.01); C07C 67/08 (2013.01); C07C 303/28 (2013.01); C07D 213/70 (2013.01); C07D 213/71 (2013.01); C07D 301/24 (2013.01); C07D 513/06 (2013.01); C07D 519/00 (2013.01); C07B 2200/13 (2013.01)]

80 Claims

1. A process for synthesizing compound Z, or a salt thereof:

comprising:

(a) admixing (2S,3S)-butane-2,3-diol, a bromide source, and acetic acid to form compound I

(b) admixing compound I and a non-nucleophilic base to form compound J

(d) admixing compound K, a leaving group reagent, and an amine base to form compound L

wherein LG is a leaving group;

(e) admixing compound L, a non-nucleophilic base, and Ar¹—SH to form compound M

wherein Ar¹is a 5-12 membered heteroaryl comprising from 1 to 3 ring heteroatoms selected from O, N, and S;

(f) oxidizing compound M to form compound N

and

(g) admixing compound N, a base and hydroxylamine-O-sulfonic acid to form compound Z.