4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone

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Chemical Name:4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone
CAS No.:1297139-58-2
Molecular Formula:C₂₇H₂₆ClFN₄O₃
Molecular Weight:508.98
Hs Code.:

Synonyms:4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone

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Chemical Property of 4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone

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Technology Process of 4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone

There total 17 articles about 4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone 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: 93.0%

: 1297139-59-3
4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyI)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}bicyclo[3.1.0]hex-3-yl)-2-piperazinone

: 1297139-58-2
4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h; Cooling with ice bath;

Reference yield:

: 1297139-24-2
(4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 1297139-58-2
4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 20 °C / Inert atmosphere

2.1: diethylzinc / dichloromethane; hexane / 0.33 h / 0 °C

2.2: 6.33 h / 0 - 20 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

4.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 20 °C

4.2: pH ~ 14

4.3: pH ~ 3

5.1: triethylamine; diphenylphosphoranyl azide / toluene / 5 h / 80 °C

5.2: 1 h / 0 - 20 °C

6.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 5 h

7.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C

8.1: potassium carbonate; thiophenol / acetonitrile / 5 h / 20 °C

9.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

9.2: 3 h / Cooling with ice bath

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Cooling with ice bath

With 2,6-dimethylpyridine; lithium hydroxide monohydrate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; dihydrogen peroxide; diethylzinc; potassium carbonate; benzotriazol-1-ol; caesium carbonate; thiophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

: 1297138-51-2
dimethyl 5-cyclopropylpyrazolo[1,5-a]pyridine-2,3-dicarboxylate

: 1297139-58-2
4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone

Guidance literature:: Multi-step reaction with 9 steps

1.1: water; sulfuric acid / 1,4-dioxane / 5 h / 85 °C

2.1: sulfuric acid / 3 h / 80 °C

3.1: N-chloro-succinimide / 1,2-dichloro-ethane / 2 h / 60 °C

4.1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / hexane / 3 h / 85 °C / sealed tube; Inert atmosphere

5.1: copper(ll) bromide / water; tetrahydrofuran; methanol / 40 °C

6.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 90 °C / Inert atmosphere

7.1: sodium hydroxide; water / tetrahydrofuran / 8 h / 20 °C

7.2: pH ~ 2

8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

8.2: 3 h / Cooling with ice bath

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Cooling with ice bath

With potassium phosphate; N-chloro-succinimide; sulfuric acid; tetrabutyl ammonium fluoride; water; N-ethyl-N,N-diisopropylamine; sodium hydroxide; copper(ll) bromide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; sulfuric acid; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;