5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxamide

Base Information

• Chemical Name: 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxamide
• CAS No.: 1403679-55-9
• Molecular Formula: C₂₂H₂₅ClN₆O
• Molecular Weight: 424.933

Synonyms:5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxamide

Chemical Property of 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxamide

Chemical Property:

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Technology Process of 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxamide

There total 4 articles about 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-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:

4-Amino-1-methylpiperidine (41838-46-4) + 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carboxylic acid (1403680-12-5) → 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxamide (1403679-55-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2014.06.025

Reference yield:

ethyl 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carboxylate (1403679-96-8) → 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxamide (1403679-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / ethanol / 20 h / Reflux

2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.06.025

Reference yield:

1-(2-amino-pyrimidin-4-yl)-2-bromo-ethanone hydrobromide (106157-91-9,845267-58-5) → 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxamide (1403679-55-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium / ethanol / 0 - 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: acetic acid; hydrogen bromide / dichloromethane / 0 - 20 °C

3.1: lithium chloride; sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethanol; toluene; water / 5 h / 100 °C / Inert atmosphere

4.1: potassium hydroxide / ethanol / 20 h / Reflux

5.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

With bis-triphenylphosphine-palladium(II) chloride; hydrogen bromide; sodium; sodium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium chloride; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 3.1: |Suzuki Coupling;

DOI:10.1016/j.bmc.2014.06.025

upstream raw materials:

4-Amino-1-methylpiperidine

5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carboxylic acid

ethyl 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carboxylate

1-(2-amino-pyrimidin-4-yl)-2-bromo-ethanone hydrobromide

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