US 11,332,442 B2Granted

Synthetic process

AssigneesBristol-Myers Squibb Company, Syngene International Limited

InventorsWilliam P. Gallagher, John Ryan Coombs, Carlos A. Guerrero, David Marcoux, Qing Shi, Candice Lee Joe, Sanjeewa Rupasinghe, Jason J. Zhu, Srinivas Kalidindi, Sathasivam Shunmugaraj, Moorthy Kandasamy, Siva Sankar Bondigela, Rajappa Vaidyanathan, Shankar Tulsidas Tendulkar, Sankar Kuppusamy, Francisco González-Bobes

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Abstract

The invention generally relates to a process for preparing compounds, including Compound of Formula (I), useful as key intermediates in the preparation of compounds having RORγt antagonist properties.

Claims4

Dependent claims

A process for the preparation of a Compound of Formula (I):

comprising the steps of
(a) reacting Compound 1 of the formula,
with 4-fluorobenzenesulfinic acid in the presence of 1-methyl-2-pyrrolidinone and iodine to afford Compound 2 of the formula,
(b) reacting Compound 2 with heptafluoroisopropyl iodide in the presence of a base to afford Compound 3 of the formula,
(c) reacting Compound 3 with a reducing agent to afford Compound 4 of the formula,
(d) reacting Compound 4 with trifluoroacetic anhydride and sodium t-pentoxide in the presence of 2-methyltetrahydrofuran to afford Compound 5 of the formula,
(e) reacting Compound 5 with Compound 6 of the formula,
in the presence of sodium t-pentoxide to afford Compound 7 of the formula,
(f) reacting Compound 7 with chlorotrimethylsilane, followed by L-(+)-tartaric acid to afford the Compound of Formula (I).

6 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/991,357Filed 12 Aug 2020
Published: US 2022/0048859 A117 Feb 2022
Granted: 17 May 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 209/60
[b]- or [c]-condensed: naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
C07C 303/40
Of amides of sulfonic acids: by reactions not involving the formation of sulfonamide groups
C07C 313/18
Sulfenic acids; Derivatives thereof: sulfenamides
C07C 315/04
Preparation of sulfones; Preparation of sulfoxides: by reactions not involving the formation of sulfone or sulfoxide groups