Tofacitinib impurity T

Base Information

• Chemical Name: Tofacitinib impurity T
• CAS No.: 1092578-43-2
• Molecular Formula: C₁₆H₂₀N₆O
• Molecular Weight: 312.374
• Mol file: 1092578-43-2.mol

Synonyms:

Chemical Property of Tofacitinib impurity T

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Tofacitinib impurity T

There total 4 articles about Tofacitinib impurity T 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: 62.5%

(3R,4R)-N,4-dimethyl-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-amine + cyanoacetic acid (372-09-8) → tofacitinib (1092578-43-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20 ℃; for 10h;

Reference yield: 60.0%

C23H26N6O3S (1092578-42-1) → tofacitinib (1092578-43-2)

Guidance literature:

With water; potassium carbonate; In methanol; for 0.5h; Reflux;

DOI:10.1021/jm801142b

Reference yield:

tert-butyl N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-N-methylcarbamate → tofacitinib (1092578-43-2)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen; palladium on activated charcoal / methanol / 10 h / 20 °C

2: potassium carbonate / 1,4-dioxane; water / 10 h / 100 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

4: O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 10 h / 20 °C

With palladium on activated charcoal; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

C₂₃H₂₆N₆O₃S

cyanoacetic acid

tert-butyl N-methyl-N-[(3R,4R)-4-methylpiperidin-3-yl]carbamate

Refernces

• 1、 Jiang, Jian-Kang,Ghoreschi, Kamran,Deflorian, Francesca,Chen, Zhi,Perreira, Melissa,Pesu, Marko,Smith, Jeremy,Nguyen, Dac-Trung,Liu, Eric H.,Leister, William,Costanzi, Stefano,O'Shea, John J.,Thomas, Craig J.. "Examining the chirality, conformation and selective kinase inhibition of 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino) piperidin-1-yl)-3-oxopropanenitrile (CP-690,550)". supporting information; experimental part. p. 8012 - 8018. Retrieved 2009/12/07.