3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile

Base Information

• Chemical Name: 3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile
• CAS No.: 460078-60-8
• Molecular Formula: C₂₈H₂₉N₇
• Molecular Weight: 463.585

Synonyms:3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile

Chemical Property of 3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile

Chemical Property:

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Technology Process of 3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile

There total 9 articles about 3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile 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: 42.0%

[2-(3-bromo-phenyl)-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-7-yl]-cyclopentyl-amine (460078-46-0) + dicyanozinc (557-21-1) → 3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile (460078-60-8)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl-formamide; at 120 ℃; for 20h;

DOI:10.1016/j.bmc.2005.05.043

Reference yield:

2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridine (460079-44-1) → 3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile (460078-60-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 46 percent / BF₃*Et₂O / toluene / Heating

2: 56 percent / rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; cesium carbonate / palladium(II) acetate / toluene / 100 °C

3: 86 percent / 144 h / Heating

4: 88 percent / K₂CO₃ / ethanol / Heating

5: 42 percent / 1,1'-bis(triphenylphosphino)ferrocene / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / dimethylformamide / 20 h / 120 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; boron trifluoride diethyl etherate; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium diacetate; In ethanol; N,N-dimethyl-formamide; toluene; 2: Buchwald-Hartwig amination;

DOI:10.1016/j.bmc.2005.05.043

Reference yield:

1-(3-bromophenyl)-2-(6-chloro-2-pyridinyl)ethanone (460079-42-9) → 3-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-benzonitrile (460078-60-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 94 percent / hydroxylamine hydrochloride; NaOH / methanol; H₂O / Heating

2.1: frifluoroacetic anhydride; triethylamine / 1,2-dimethoxy-ethane / 0 - 20 °C

2.2: 44 percent / iron(II) chloride / 1,2-dimethoxy-ethane / 8 h / Heating

3.1: 46 percent / BF₃*Et₂O / toluene / Heating

4.1: 56 percent / rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; cesium carbonate / palladium(II) acetate / toluene / 100 °C

5.1: 86 percent / 144 h / Heating

6.1: 88 percent / K₂CO₃ / ethanol / Heating

7.1: 42 percent / 1,1'-bis(triphenylphosphino)ferrocene / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / dimethylformamide / 20 h / 120 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; sodium hydroxide; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; trifluoroacetic anhydride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium diacetate; In methanol; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; toluene; 4.1: Buchwald-Hartwig amination;

DOI:10.1016/j.bmc.2005.05.043

upstream raw materials:

[2-(3-bromo-phenyl)-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-7-yl]-cyclopentyl-amine

dicyanozinc

2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridine

1-(3-bromophenyl)-2-(6-chloro-2-pyridinyl)ethanone

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