IP Library Granted Patent US 12,331,047
Granted Patent B2
US 12,331,047 · App. 17/310,123 · Granted Jun 17, 2025

Synthesis for 3-bromo-5-(2-ethylimidazo[1, 2-alpha]pyridine-3-carbonyl)-2-hydroxybenzonitrile

Inventors: Dongfang Shi (Fremont, CA); Changjin Fu (Suzhou, CN); Jie Gu (Suzhou, CN); Min Zhang (Suzhou, CN); Weiwei Gong (Suzhou, CN); Pengfei Li (Suzhou, CN)
Assignee: Atom Therapeutics Co., Ltd
C07D471/04
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,331,047
App. No.
17/310,123
Granted
Jun 17, 2025
Kind
B2
Abstract

A method for synthesizing 3-bromo-5-(2-ethylimidazo[1,2-a] pyridine-3-carbonyl)-2-hydroxybenzonitrile, particularly relates to a method for synthesizing a compound represented by a formula (III), and particularly relates to step A or step B; step A: a compound represented by a formula (I) and a compound represented by a formula (II) are first heated in an organic solvent to react, and the resulting reaction product and a base are heated in the presence of water to continue the reaction to obtain a compound represented by a formula (III); and step B: a compound represented by the formula (I), a compound represented by a formula (II), and a base are heated in an organic solvent to react, and the resulting reaction product is heated in the presence of water to continue the reaction to obtain a compound represented by a formula (III).

Claims (10)

1. A method for synthesizing a compound represented by formula (III), comprising step A or step B,

Step A: a compound represented by formula (I) and a compound represented by formula (II) are first heated in an organic solvent to react, and the resulting reaction product and a base are heated in the presence of water to continue the reaction to obtain a compound represented by formula (III);

Step B: a compound represented by formula (I), a compound represented by formula (II), and the base are heated in an organic solvent to react, and the resulting reaction product is heated in the presence of water to continue the reaction to obtain a compound represented by formula (III);

wherein, R 1 is H or C1-3 alkyl, R 2 is H, —CN, I or Br, R 3 is H, I or Br, and R 4 is Cl, Br or I; the organic solvent is selected from the group consisting of toluene, xylene, ethyl acetate, isopropyl acetate, isopropanol, ethanol, N-methyl-2-pyrrolidone (NMP), tert-butanol, dimethylformamide (DMF) and acetonitrile;

wherein the base is selected from the group consisting of sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, triethylamine, diisopropylethylamine, lithium hydroxide, sodium hydroxide and potassium hydroxide.

2. The method according to claim 1 , wherein the reaction temperature of the compound represented by formula (I) and the compound represented by formula (II) is 75 to 150° C. the temperature for continuing the reaction is 50 to 100° C.

3. The method according to claim 1 , wherein the organic solvent is ethyl acetate.

4. The method according to claim 1 , wherein in step A, the base is added to such an amount that the pH value of the reaction solution that continues to react reaches 4 to 7; in step B, the amount of the base added is 0.1 to 2.5 times the moles of the compound represented by formula (II).

5. The method according to claim 2 , wherein the reaction temperature of the compound represented by formula (I) and the compound represented by formula (II) is 77 to 100° C.; the temperature for continuing the reaction is 60 to 100° C.

6. The method according to claim 4 , wherein the base is sodium bicarbonate; in step B, the amount of the base added is 0.5 to 2.5 times the moles of the compound represented by formula (II).

Assignments (2)
CHANGE OF NAME Recorded May 13, 2025
From: JIANGSU ATOM BIOSCIENCE AND PHARMACEUTICAL CO., LTD.,
To: ATOM THERAPEUTICS CO., LTD
Reel/Frame 071094/0310 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2021
From: SHI, DONGFANG; FU, CHANGJIN; GU, JIE; ZHANG, MIN; GONG, WEIWEI; LI, PENGFEI
To: JIANGSU ATOM BIOSCIENCE AND PHARMACEUTICAL CO., LTD.
Reel/Frame 056892/0606 →
Priority Claims (2)
CN 201910057056.3 · Jan 19, 2019 · national
CN 202010037085.6 · Jan 14, 2020 · national
Continuity (1)
Related Publication 20220041593A1 · Feb 10, 2022
References Cited (1)
WO 2018090921 · 2018 [cited by examiner]