N-((3S,4S)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine

Base Information

• Chemical Name: N-((3S,4S)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine
• CAS No.: 1252883-90-1
• Molecular Formula: C20H25N5
• Molecular Weight: 335.452
• Mol file: 1252883-90-1.mol

Synonyms:N-((3S,4S)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine;N-Methyl-N-[(3S,4S)-4-methyl-1-(phenylmethyl)-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine;Tofacitinib IMpurity P

Chemical Property of N-((3S,4S)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine

Chemical Property:

• PKA: 13.36±0.50(Predicted)
• PSA: 48.05000
• Density: 1.205±0.06 g/cm3(Predicted)
• LogP: 3.24260
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

TofacitinibimpurityP ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Tofacitinib impurity P is an impurity of Tofacitinib (T528000), an enantiopure stereoisomer of the drug, Janus kinase 3(Jak3) inhibitor (CP-690,550) that has been found to inhibit selected members of the STE7 and STE20 subfamily of kinases.

Technology Process of N-((3S,4S)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine

There total 4 articles about N-((3S,4S)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine 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: 70.0%

N-methyl-N-((3S,4S)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1260614-73-0) + benzyl bromide (100-39-0) → N-((3S,4S)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d] pyrimidin-4-amine (1252883-90-1)

Guidance literature:

With copper; caesium carbonate; methyl-alpha-D-glucopyranoside; In water; dimethyl sulfoxide; at 100 - 110 ℃; Sealed tube; Green chemistry;

DOI:10.1055/s-0039-1690702

Reference yield: 40.0%

methyl(1-phenylmethyl-4-methylpiperidin-3-yl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine (384337-90-0) → ((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amine + N-((3S,4S)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d] pyrimidin-4-amine (1252883-90-1)

Guidance literature:

With triethylamine; In hexane; isopropyl alcohol; Purification / work up; Resolution of racemate;

Reference yield:

cis-N-benzyl-3-methoxycarbonylamino-4-methylpiperidine (1354621-59-2,1431697-80-1,477600-69-4) + 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → ((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amine + N-((3S,4S)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d] pyrimidin-4-amine (1252883-90-1)

Guidance literature:

cis-N-benzyl-3-methoxycarbonylamino-4-methylpiperidine; 4-chloro-1H-pyrrolo[2,3-d]pyrimidine; With triethylamine; at 100 ℃; for 96h;

In ethanol; hexane; Resolution of racemate;

DOI:10.1021/jm1004286

upstream raw materials:

methyl(1-phenylmethyl-4-methylpiperidin-3-yl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine

cis-N-benzyl-3-methoxycarbonylamino-4-methylpiperidine

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

N-methyl-N-((3S,4S)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Downstream raw materials:

N-methyl-N-((3S,4S)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile monocitrate

Refernces

• 1、 -. "PIPERIDINE INHIBITORS OF JANUS KINASE 3". Page/Page column 53. . Retrieved 2010/11/05.
• 2、 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.