N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

Base Information

Chemical Name:N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide
CAS No.:1383485-79-7
Molecular Formula:C₂₂H₂₁F₃N₈O
Molecular Weight:470.457
Hs Code.:

Synonyms:N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

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Chemical Property of N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

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Technology Process of N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

There total 8 articles about N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-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:

: 1383485-63-9
N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1-trityl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

: 1383485-79-7
N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

Guidance literature:: With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

Reference yield:

: 38186-88-8
2-chloro-5-fluoronicotinic acid

: 1383485-79-7
N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C / Inert atmosphere

1.2: 0.25 h / 0 °C

2.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.75 h / 0 °C

3.1: hydrazine hydrate / butan-1-ol / 4.5 h / Reflux

4.1: tert.-butylnitrite; Bromoform / 2 h / 61 - 90 °C

5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

6.1: potassium acetate / palladium bis[bis(diphenylphosphino)ferrocene] dichloride / N,N-dimethyl-formamide / 1.5 h / 100 °C / Inert atmosphere

7.1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / water / 1 h / 120 °C / Inert atmosphere

8.1: triethylsilane; trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

With triethylsilane; potassium phosphate; tert.-butylnitrite; oxalyl dichloride; Bromoform; potassium acetate; potassium carbonate; hydrazine hydrate; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; N,N-dimethyl-formamide; XPhos; In dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;

Reference yield:

: 791644-48-9
2-chloro-5-fluoronicotinonitrile

: 1383485-79-7
N-((1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1: hydrazine hydrate / butan-1-ol / 4.5 h / Reflux

2: tert.-butylnitrite; Bromoform / 2 h / 61 - 90 °C

3: potassium carbonate / N,N-dimethyl-formamide / 20 °C

4: potassium acetate / palladium bis[bis(diphenylphosphino)ferrocene] dichloride / N,N-dimethyl-formamide / 1.5 h / 100 °C / Inert atmosphere

5: potassium phosphate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / water / 1 h / 120 °C / Inert atmosphere

6: triethylsilane; trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

With triethylsilane; potassium phosphate; tert.-butylnitrite; Bromoform; potassium acetate; potassium carbonate; hydrazine hydrate; trifluoroacetic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; XPhos; In dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;