tofacitinib iMpurity

Base Information

• Chemical Name: tofacitinib iMpurity
• CAS No.: 1640971-60-3
• Molecular Formula: C₁₄H₂₀N₆O
• Molecular Weight: 288.352
• Mol file: 1640971-60-3.mol

Synonyms:

Chemical Property of tofacitinib iMpurity

Chemical Property:

• Melting Point: 238 - 240°C
• Boiling Point: 551.0±50.0 °C(Predicted)
• PKA: 6.06±0.60(Predicted)
• Density: 1.249±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

TofacitinibCitrateImpurity ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Tofacitinib Citrate Impurity is derived from (3R,?4R)?-N,?4-?Dimethyl-?1-?benzyl?-3-?piperidinamine (D464895), which is a reagent used in the preparation of Janus tyrosine kinase inhibitors for the treatment of autoimmune diseases.

Technology Process of tofacitinib iMpurity

There total 4 articles about tofacitinib iMpurity 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:

C11H19N5 + cyanoacetic acid (372-09-8) → 3-[(3R,4R)-3-[(6-aminopyrimidin-4-yl)(methyl)amino]-4-methylpiperidin-1-yl]-3-oxopropanenitrile (1640971-60-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere; Schlenk technique;

DOI:10.1002/cmdc.201402252

Reference yield:

N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-6-chloro-N-methylpyrimidin-4-amine → 3-[(3R,4R)-3-[(6-aminopyrimidin-4-yl)(methyl)amino]-4-methylpiperidin-1-yl]-3-oxopropanenitrile (1640971-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium hexamethyldisilazane; tri tert-butylphosphoniumtetrafluoroborate / 1,4-dioxane / 18 h / 65 - 80 °C / Sealed tube

1.2: 20 °C

2.1: hydrogen; palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal / methanol / 40 °C / 3000.3 Torr

3.1: dicyclohexyl-carbodiimide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Schlenk technique

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal; hydrogen; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1002/cmdc.201402252

Reference yield:

4-N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-4-N-methylpyrimidine-4,6-diamine → 3-[(3R,4R)-3-[(6-aminopyrimidin-4-yl)(methyl)amino]-4-methylpiperidin-1-yl]-3-oxopropanenitrile (1640971-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal / methanol / 40 °C / 3000.3 Torr

2: dicyclohexyl-carbodiimide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Schlenk technique

With palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal; hydrogen; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1002/cmdc.201402252

upstream raw materials:

cyanoacetic acid

N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine