3-((3R,4R)-3-((2-chloro-7H-pyrrolo[2,3-d]pyriMidin-4-yl)(Methyl)aMino)-4-Methylpiperidin-1-yl)-3-oxopropanenitrile

Base Information

• Chemical Name: 3-((3R,4R)-3-((2-chloro-7H-pyrrolo[2,3-d]pyriMidin-4-yl)(Methyl)aMino)-4-Methylpiperidin-1-yl)-3-oxopropanenitrile
• CAS No.: 1616761-00-2
• Molecular Formula: C₁₆H₁₉ClN₆O
• Molecular Weight: 346.819
• Mol file: 1616761-00-2.mol

Synonyms:

Chemical Property of 3-((3R,4R)-3-((2-chloro-7H-pyrrolo[2,3-d]pyriMidin-4-yl)(Methyl)aMino)-4-Methylpiperidin-1-yl)-3-oxopropanenitrile

Chemical Property:

• PKA: 6.06±0.60(Predicted)
• Density: 1.371±0.06 g/cm3(Predicted)

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Methyl-N-(3R,4R)-1-cyanoacetyl-4-methylpiperidin-3-yl-2-chloro-7-deazapurine-6-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-Methyl-N-(3R,4R)-1-cyanoacetyl-4-methylpiperidin-3-yl-2-chloro-7-deazapurine-6-amine is a Tasocitinib (Tofacitinib [T528000]) impurity.

Technology Process of 3-((3R,4R)-3-((2-chloro-7H-pyrrolo[2,3-d]pyriMidin-4-yl)(Methyl)aMino)-4-Methylpiperidin-1-yl)-3-oxopropanenitrile

There total 7 articles about 3-((3R,4R)-3-((2-chloro-7H-pyrrolo[2,3-d]pyriMidin-4-yl)(Methyl)aMino)-4-Methylpiperidin-1-yl)-3-oxopropanenitrile 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: 82.0%

3-[(3R,4R)-3-{[2-chloro-7-(4-methylbenzenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl](methyl)amino}-4-methylpiperidin-1-yl]-3-oxopropanenitrile → 3-[(3R,4R)-3-({2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl}(methyl)amino)-4-methylpiperidin-1-yl]-3-oxopropanenitrile (1616761-00-2)

Guidance literature:

With methanol; caesium carbonate; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1002/cmdc.201402252

Reference yield:

N-((3R,4R)-4-methyl-piperidin-3-yl)-N-methyl-2-chloro-7H-pyrrolo[2,3-D]pyrimidine-4-amine (1616760-97-4) + cyanoacetic acid (372-09-8) → 3-[(3R,4R)-3-({2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl}(methyl)amino)-4-methylpiperidin-1-yl]-3-oxopropanenitrile (1616761-00-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In butan-1-ol; at 40 ℃; for 8h; Temperature;

Reference yield:

tert-butyl N-methyl-N-[(3R,4R)-4-methylpiperidin-3-yl]carbamate (1206824-89-6,1419075-90-3) → 3-[(3R,4R)-3-({2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl}(methyl)amino)-4-methylpiperidin-1-yl]-3-oxopropanenitrile (1616761-00-2)

Guidance literature:

Multi-step reaction with 4 steps

1: dicyclohexyl-carbodiimide / dichloromethane / 3.25 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

2: hydrogenchloride / 1,4-dioxane / 20 °C / Inert atmosphere; Schlenk technique

3: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 24 h / 105 °C / Inert atmosphere; Sealed tube

4: caesium carbonate; methanol / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

With hydrogenchloride; methanol; caesium carbonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1002/cmdc.201402252

upstream raw materials:

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

2,4-dichloro-7-p-methylbenzenesulfonyl-7H-pyrrole[2,3-d]pyrimidin-4-amine

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

N-((3R,4R)-4-methyl-piperidin-3-yl)-N-methyl-2-chloro-7H-pyrrolo[2,3-D]pyrimidine-4-amine