3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide

Base Information

• Chemical Name: 3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide
• CAS No.: 1612842-43-9
• Molecular Formula: C₂₄H₁₈Cl₂F₂N₄O₄
• Molecular Weight: 535.334

Synonyms:3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide

Chemical Property of 3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide

Chemical Property:

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Technology Process of 3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide

There total 8 articles about 3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

4-(4-amino-2-fluorophenoxy)-3-chloropyridine-2-carboxamide (1025721-01-0) + 3-bromo-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid (1612842-40-6) → 3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide (1612842-43-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.3390/molecules19022655

Reference yield:

piperidin-2-one (675-20-7) → 3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide (1612842-43-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium phosphate; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere

2.1: tert.-butyl lithium / tetrahydrofuran / 4 h / -78 °C / Inert atmosphere

2.2: 0.17 h / Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 5 h / 0 - 20 °C / Inert atmosphere

4.1: bromine / diethyl ether / 2 h / 0 °C / Inert atmosphere

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With dmap; potassium phosphate; copper(l) iodide; lithium hydroxide monohydrate; bromine; tert.-butyl lithium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.3390/molecules19022655

Reference yield:

4-fluoro-1-iodobenzene (352-34-1) → 3-chloro-4-(4-(3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamido)-2-fluorophenoxy)-picolinamide (1612842-43-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium phosphate; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere

2.1: tert.-butyl lithium / tetrahydrofuran / 4 h / -78 °C / Inert atmosphere

2.2: 0.17 h / Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 5 h / 0 - 20 °C / Inert atmosphere

4.1: bromine / diethyl ether / 2 h / 0 °C / Inert atmosphere

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With dmap; potassium phosphate; copper(l) iodide; lithium hydroxide monohydrate; bromine; tert.-butyl lithium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.3390/molecules19022655

upstream raw materials:

3,4-dichloropyridine

3,4-dichloropyridine-2-carboxamide

4-(4-amino-2-fluorophenoxy)-3-chloropyridine-2-carboxamide

3-bromo-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid

Downstream raw materials:

N-(4-((2-amino-3-chloropyridin-4-yl)oxy)-3-fluorophenyl)-3-chloro-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamide

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