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US 12,441,681 B2Granted
Synthesis of sulfonamide intermediates
AssigneesAmgen Inc., F.I.S. Fabbrica Italiana Sintetici S.p.A.
InventorsNeil Fred Langille, Jason S. Tedrow, Jonathan Vinh-Phu Truong, Robert Ronald Milburn, Alessandro Arena
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Abstract
Provided herein are processes for synthesizing Mcl-1 inhibitors and intermediates such as compound Z that can be used to prepare them. In particular, provided herein are processes for synthesizing compound A1, and salts or solvates thereof and compound A2, and salts and solvates thereof.
Claims80
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
- (c) admixing compound J and an allyl nucleophile to form compound K
- (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 Ar1 is 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.
8 more elements
Dependencies are inferred from the claim text.