3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

Base Information

Chemical Name:3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile
CAS No.:1414356-75-4
Molecular Formula:C₂₅H₂₁F₂N₇O₂
Molecular Weight:489.484
Hs Code.:

Synonyms:3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

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Chemical Property of 3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

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Technology Process of 3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

There total 13 articles about 3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-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: 58.0%

: 1414356-73-2
3-[4-(2,5-difluorophenoxy)phenyl]-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

: 372-09-8
cyanoacetic acid

: 1414356-75-4
3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

Guidance literature:: With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 25 ℃; for 10h;

Reference yield:

: 151266-23-8
4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

: 1414356-75-4
3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

Guidance literature:: Multi-step reaction with 4 steps

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

2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 3 h / 25 °C

4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / dichloromethane / 10 h / 25 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-isopropyl azodicarboxylate; sodium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1: |Mitsunobu Displacement;

Reference yield:

: 2380-63-4
4-Aminopyrazolo<3,4-d>pyrimidin

: 1414356-75-4
3-[(3R)-3-[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere

4: trifluoroacetic acid / dichloromethane / 3 h / 25 °C

5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / dichloromethane / 10 h / 25 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; caesium carbonate; triethylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;