5-chloro-N₂-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine

Base Information

• Chemical Name: 5-chloro-N₂-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine
• CAS No.: 1445895-01-1
• Molecular Formula: C₃₀H₃₉ClN₄O₃S
• Molecular Weight: 571.184

Synonyms:5-chloro-N₂-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine

Chemical Property of 5-chloro-N₂-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine

Chemical Property:

Purity/Quality:

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Technology Process of 5-chloro-N₂-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine

There total 7 articles about 5-chloro-N₂-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine 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: 11.0%

4-bromo-5-chloro-N-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)pyridin-2-amine (1445894-99-4) + 1-amino-2-(isopropylsulphonyl)benzene (76697-50-2) → 5-chloro-N2-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine (1445895-01-1)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl[2-(2,4,6-triisopropylphenyl)phenyl]phosphane; sodium t-butanolate; In tetrahydrofuran; at 150 ℃; Microwave irradiation;

DOI:10.1021/jm400402q

Reference yield:

1-chloro-5-fluoro-2-methyl-4-nitrobenzene (112108-73-3) → 5-chloro-N2-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine (1445895-01-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: caesium carbonate / 60 °C

2.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / 1,4-dioxane; water / 0.33 h / 150 °C / Inert atmosphere; Microwave irradiation

3.1: tetrahydrofuran / 48 h / 40 °C / Sealed tube

4.1: sodium tetrahydroborate / methanol / 2.5 h / 0 - 20 °C

4.2: 14 h / 2585.81 Torr

5.1: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 0.67 h / 150 °C / Microwave irradiation

6.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl[2-(2,4,6-triisopropylphenyl)phenyl]phosphane; sodium t-butanolate / tetrahydrofuran / 150 °C / Microwave irradiation

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium tetrahydroborate; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl[2-(2,4,6-triisopropylphenyl)phenyl]phosphane; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; methanol; water; 2.1: |Suzuki Coupling / 5.1: |Buchwald-Hartwig Coupling;

DOI:10.1021/jm400402q

Reference yield:

4-[2-methyl-4-nitro-5-(propan-2-yloxy)phenyl]pyridine (1032903-62-0) → 5-chloro-N2-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyridine-2,4-diamine (1445895-01-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 48 h / 40 °C / Sealed tube

2.1: sodium tetrahydroborate / methanol / 2.5 h / 0 - 20 °C

2.2: 14 h / 2585.81 Torr

3.1: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 0.67 h / 150 °C / Microwave irradiation

4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl[2-(2,4,6-triisopropylphenyl)phenyl]phosphane; sodium t-butanolate / tetrahydrofuran / 150 °C / Microwave irradiation

With sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl[2-(2,4,6-triisopropylphenyl)phenyl]phosphane; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; In tetrahydrofuran; methanol; 3.1: |Buchwald-Hartwig Coupling;

DOI:10.1021/jm400402q

upstream raw materials:

1-chloro-5-fluoro-2-methyl-4-nitrobenzene

1-chloro-2-methyl-4-nitro-5-(propan-2-yloxy)benzene

4-[2-methyl-4-nitro-5-(propan-2-yloxy)phenyl]pyridine

2-isopropoxy-5-methyl-4-(1-methyl-piperidin-4-yl)-phenylamine

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