(R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile

Base Information

• Chemical Name: (R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile
• CAS No.: 1414356-49-2
• Molecular Formula: C₂₉H₂₆FN₇O₂
• Molecular Weight: 523.57
• Mol file: 1414356-49-2.mol

Synonyms:(R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile

Chemical Property of (R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile

There total 12 articles about (R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile 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: 27.0%

3-[(3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile (1414356-52-7) + Cyclopropanecarboxaldehyde (1489-69-6) → (R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile (1414356-49-2)

Guidance literature:

With piperidine; In methanol; at 20 ℃; for 12h;

Reference yield:

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (151266-23-8) → (R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile (1414356-49-2)

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 72 h / 20 - 70 °C

2: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; monoethylene glycol diethyl ether / 80 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 12 h / 20 °C

4: 1,1'-carbonyldiimidazole / dichloromethane / 24 h / 20 °C

5: piperidine / methanol / 12 h / 20 °C

With piperidine; di-isopropyl azodicarboxylate; sodium carbonate; triphenylphosphine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; monoethylene glycol diethyl ether; water;

Reference yield:

4-Aminopyrazolo<3,4-d>pyrimidin (2380-63-4) → (R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile (1414356-49-2)

Guidance literature:

Multi-step reaction with 6 steps

1: N-iodo-succinimide / N,N-dimethyl-formamide / 20 - 60 °C

2: caesium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C

3: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; monoethylene glycol diethyl ether / 80 °C / Inert atmosphere

4: trifluoroacetic acid / dichloromethane / 12 h / 20 °C

5: 1,1'-carbonyldiimidazole / dichloromethane / 24 h / 20 °C

6: piperidine / methanol / 12 h / 20 °C

With piperidine; N-iodo-succinimide; sodium carbonate; caesium carbonate; 1,1'-carbonyldiimidazole; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; dichloromethane; monoethylene glycol diethyl ether; water; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate

3-[(3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

Cyclopropanecarboxaldehyde

3-fluorophenylboronic acid