N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Base Information

• Chemical Name: N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
• CAS No.: 1260162-58-0
• Molecular Formula: C₁₈H₁₃ClF₂N₆O₂
• Molecular Weight: 418.79

Synonyms:N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Chemical Property of N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

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Technology Process of N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

There total 4 articles about N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 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: 65.0%

pyrazolo[1,5-a]pyrimidine-3-carboxamide (774549-55-2) + 3-(5-chloro-2-(difluoromethoxy)phenyl)-4-iodo-1-methyl-1H-pyrazole → N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (1260162-58-0)

Guidance literature:

With potassium phosphate; copper(l) iodide; In 1,4-dioxane; at 100 ℃; for 30h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.1c02518

Reference yield:

2-bromo-4-chlorophenol (695-96-5) → N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (1260162-58-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: caesium carbonate / water / 12 h / 25 - 100 °C

2.1: potassium carbonate; trimethylpyruvic acid; catacxium A; palladium diacetate / N,N-dimethyl acetamide / 12 h / 100 °C / Inert atmosphere

3.1: hydrogenchloride / water; ethanol / 2.5 h / 75 °C

4.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 40 °C

4.2: 1 h / 75 °C

5.1: ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; dmap / N,N-dimethyl-formamide / 16 h / 50 °C

With hydrogenchloride; dmap; palladium diacetate; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; trimethylpyruvic acid; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); catacxium A; In ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2019.04.008

Reference yield:

2-bromo-4-chloro-1-(difluoromethoxy)benzene (1214348-81-8) → N-(3-(5-chloro-2-(difluoromethoxy)phenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (1260162-58-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate; trimethylpyruvic acid; catacxium A; palladium diacetate / N,N-dimethyl acetamide / 12 h / 100 °C / Inert atmosphere

2.1: hydrogenchloride / water; ethanol / 2.5 h / 75 °C

3.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 40 °C

3.2: 1 h / 75 °C

4.1: ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; dmap / N,N-dimethyl-formamide / 16 h / 50 °C

With hydrogenchloride; dmap; palladium diacetate; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; trimethylpyruvic acid; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); catacxium A; In ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2019.04.008

upstream raw materials:

2-bromo-4-chlorophenol

2-bromo-4-chloro-1-(difluoromethoxy)benzene

pyrazolo[1,5-a]pyrimidine-3-carboxamide

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