3-Pyridinecarbonitrile,5-(1S,5S)-3,6-diazabicyclo[3.2.0]hept-3-yl-(9CI)

Base Information

• Chemical Name: 3-Pyridinecarbonitrile,5-(1S,5S)-3,6-diazabicyclo[3.2.0]hept-3-yl-(9CI)
• CAS No.: 799279-93-9
• Molecular Formula: C₁₁H₁₂N₄
• Molecular Weight: 200.243
• Mol file: 799279-93-9.mol

Synonyms:5-[(1S,5S)-3,6-Diazabicyclo[3.2.0]hept-3-yl]nicotinonitrile

Chemical Property of 3-Pyridinecarbonitrile,5-(1S,5S)-3,6-diazabicyclo[3.2.0]hept-3-yl-(9CI)

Chemical Property:

• PSA: 51.95000
• LogP: 0.75508

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Pyridinecarbonitrile,5-(1S,5S)-3,6-diazabicyclo[3.2.0]hept-3-yl-(9CI)

There total 7 articles about 3-Pyridinecarbonitrile,5-(1S,5S)-3,6-diazabicyclo[3.2.0]hept-3-yl-(9CI) 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: 90.0%

tert-butyl (1R,5S)-3-(5-cyano-pyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate (956276-79-2) → 5-[(1S,5S)-3,6-diazabicyclo[3.2.0]heptan-3-yl]nicotinonitrile (799279-93-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/jm070755h

Reference yield:

tert-butyl (1S,5R)-3-(5-cyano-pyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate (370882-62-5) → 5-[(1R,5R)-3,6-diazabicyclo[3.2.0]heptan-3-yl]nicotinonitrile (799279-93-9)

Guidance literature:

In trifluoroacetic acid; at 65 ℃; for 1h;

DOI:10.1016/j.bcp.2007.08.010

Reference yield:

(1R,5S)-tert-butyl 3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylate (799279-81-5) → 5-[(1S,5S)-3,6-diazabicyclo[3.2.0]heptan-3-yl]nicotinonitrile (799279-93-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Cs₂CO₃; BINAP / Pd₂(dba)3 / toluene / 40 h / 110 °C

2: trifluoroacetic acid / 1 h / 65 °C

With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; trifluoroacetic acid;

DOI:10.1016/j.bcp.2007.08.010

upstream raw materials:

tert-butyl (1R,5S)-3-(5-cyano-pyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate

(1R,5S)-tert-butyl 3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylate

5-bromopyridine-3-carbonitrile

tert-butyl (1S,5R)-3-(5-cyano-pyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate