3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ⁶-sulphanyl)benzamide

Base Information

• Chemical Name: 3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ⁶-sulphanyl)benzamide
• CAS No.: 1448315-53-4
• Molecular Formula: C₂₄H₁₈F₅N₅O₂S
• Molecular Weight: 535.497

Synonyms:3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ⁶-sulphanyl)benzamide

Chemical Property of 3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ⁶-sulphanyl)benzamide

Chemical Property:

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Technology Process of 3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ⁶-sulphanyl)benzamide

There total 7 articles about 3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ⁶-sulphanyl)benzamide 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: 31.0%

3-hydroxy-5-(pentafluoro-λ6-sulphanyl)benzoic acid (1180672-84-7) + 4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline (1448317-23-4) → 3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ6-sulphanyl)benzamide (1448315-53-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

Reference yield:

nicotinoylacetonitrile (30510-18-0) → 3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ6-sulphanyl)benzamide (1448315-53-4)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogenchloride / ethanol; water / 4 h / Reflux

2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; caesium carbonate / 1,4-dioxane / 4 h / Inert atmosphere; Reflux

3: sulfuric acid / ethanol / 4 h / Reflux

4: hydrogen; palladium 10% on activated carbon / ethanol / 48 h / 760.05 Torr

5: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 48 h / 20 °C

With hydrogenchloride; sulfuric acid; palladium 10% on activated carbon; hydrogen; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;

Reference yield:

1-(2,2-diethoxyethyl)-3-(pyridin-3-yl)-1H-pyrazole-5-amine (222056-48-6) → 3-hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-λ6-sulphanyl)benzamide (1448315-53-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; caesium carbonate / 1,4-dioxane / 4 h / Inert atmosphere; Reflux

2: sulfuric acid / ethanol / 4 h / Reflux

3: hydrogen; palladium 10% on activated carbon / ethanol / 48 h / 760.05 Torr

4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 48 h / 20 °C

With sulfuric acid; palladium 10% on activated carbon; hydrogen; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

nicotinoylacetonitrile

1-(2,2-diethoxyethyl)-3-(pyridin-3-yl)-1H-pyrazole-5-amine

1-(2,2-diethoxyethyl)-N-(2-methyl-5-nitrophenyl)-3-(pyridin-3-yl)-1H-pyrazole-5-amine

1-(2-methyl-5-nitrophenyl)-6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazole

Downstream raw materials:

N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-λ⁶-sulphanyl)-5-(pyrrolidin-3-yloxy)benzamide

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