(+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile

Base Information

• Chemical Name: (+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile
• CAS No.: 1257068-13-5
• Molecular Formula: C₂₄H₂₂N₈O₂S
• Molecular Weight: 486.557
• Mol file: 1257068-13-5.mol

Synonyms:(+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile

Chemical Property of (+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile

There total 8 articles about (+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)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:

tert-butyl 3-formylpyrrolidine-1-carboxylate (59379-02-1,191348-04-6) → (+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile (1257068-13-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 - 20 °C

1.2: 16 h / 0 - 20 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 72 h

3.1: hydrogenchloride / 1,4-dioxane / 16 h

4.1: N-ethyl-N,N-diisopropylamine; boron trifluoride; 1-butyl-3-methyl-3H-imidazol-1-ium fluoride / 5.2 h / 120 - 150 °C

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h

5.2: 1 h

5.3: 1 h

With hydrogenchloride; 1-butyl-3-methyl-3H-imidazol-1-ium fluoride; boron trifluoride; potassium tert-butylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetonitrile;

Reference yield:

2-(3-{2-cyano-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylthio)benzonitrile (1257075-52-7) → (+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile (1257068-13-5)

Guidance literature:

2-(3-{2-cyano-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylthio)benzonitrile; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1.5h;

With trifluoroacetic acid; In 1,2-dichloro-ethane; for 1h;

With ethylenediamine; In methanol; for 1h;

Reference yield:

benzyl 3-{2-cyano-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidine-1-carboxylate (941687-73-6) → (+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile (1257068-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 2585.81 Torr

2.1: N-ethyl-N,N-diisopropylamine; boron trifluoride; 1-butyl-3-methyl-3H-imidazol-1-ium fluoride / 5.2 h / 120 - 150 °C

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h

3.2: 1 h

3.3: 1 h

With 1-butyl-3-methyl-3H-imidazol-1-ium fluoride; boron trifluoride; hydrogen; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium 10% on activated carbon; In methanol; dichloromethane;

upstream raw materials:

2-(3-{2-cyano-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylthio)benzonitrile

2,6 difluorobenzonitrile

2-fluoro-6-(methylthio)benzonitrile

tert-butyl 3-formylpyrrolidine-1-carboxylate