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US 2023/0416210 A1Published application
Methods of making a ppar-delta agonist
AssigneeReneo Pharmaceuticals, Inc.
InventorMichael Trevelyan WILLIAMS
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Abstract
Described herein are methods of making the PPARδ agonist compound (E)-2-(4-((3-(4-fluorophenyl)-3-(4-(3-morpholinoprop-1-yn-1-yl)phenyl)allyl)oxy)-2-methylphenoxy)acetic acid, including salt forms thereof.
Claims76
A process for the preparation of Compound II:
- comprising:
- (1) reacting Compound 3, or a salt thereof:
- wherein B is a boronic acid, boronate ester, or trifluoroborate;
- with Compound 4:
- wherein R is C1-C6 alkyl;
- and
- X is Br or I;
- in the presence of a coupling catalyst, a suitable base, and in a suitable solvent, to provide Compound 5, or a salt thereof:
- wherein R is C1-C6 alkyl;
- (2) (i) reacting Compound 5 with sodium hydroxide, potassium hydroxide, or lithium hydroxide in a suitable solvent to provide Compound 6:
- wherein M is sodium, potassium, or lithium;
- and
- (ii) contacting Compound 6 with a suitable acid in a suitable solvent to provide Compound I:
- and
- (3) reacting Compound I with a sodium hydroxide solution in the presence of a suitable solvent to provide Compound II.
12 more elements
A process for the preparation of Compound 5, or a salt thereof:
- wherein R is C1-C6 alkyl;
- comprising:
- reacting Compound 3, or a salt thereof:
- wherein B is a boronic acid, boronate ester, or trifluoroborate;
- with Compound 4:
- wherein R is C1-C6 alkyl;
- and
- X is Br or I;
- in the presence of a coupling catalyst, a suitable base, and in a suitable solvent, to provide Compound 5.
6 more elements
A process for the preparation of Compound 3, or salt thereof:
- wherein B is a boronic acid, boronate ester, or trifluoroborate
- comprising reacting Compound 1:
- wherein X′ is Cl, Br or I;
- with Compound 2, or salt thereof:
- in the presence of a coupling catalyst, a suitable copper(I) cocatalyst, a suitable base, and in a suitable solvent.
2 more elements
The compound 4-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)prop-2-yn-1-yl)morpholine hydrochloride (Compound 3b):
A compound having the following structure of Compound 4c:
A process for the preparation of Compound 4:
- wherein X is Br or I;
- comprising reacting Compound 4-8:
- with Compound 4-4:
- wherein X is Br or I;
- and Y is Br or Cl;
- in the presence of a suitable base and in a suitable solvent to provide Compound 4.
3 more elements
Dependencies are inferred from the claim text.