What is the Ibrutinib?

Ibrutinib is , while it's Molecular Formula is C 25 H 24 N 6 O 2 . Ibrutinib is a highly selective Bruton’s tyrosine kinase (Btk) irreversible inhibitor.

What is the CAS number for Ibrutinib?

The CAS number of Ibrutinib is 936563-96-1.

What is Ibrutinib (936563-96-1) used for?

In November 2013, the US FDA approved ibrutinib (also referred to as PCI-32765), for the treatment of patients with mantle cell lymphoma (MCL) who had received at least one prior therapy. Ibrutinib is the second oral agent approved for the treatment of MCL. It works by irreversibly inhibiting Bruton’s tyrosine kinase (Btk) leading to the inhibition of B-cell receptor signaling and resulting in the reduction of malignant B-cell proliferation and induction of cell death. Btk plays an important role in the differentiation, development, proliferation, and survival of B cells via activation of cell-cycle regulators and regulating the expression of pro- and antiapoptotic proteins. Aberrant Btk activity results in a variety of B-cell malignancies including MCL. Ibrutinib inhibits Btk by irreversibly binding to cysteine-481 in the active site thereby inhibiting phosphorylation of tyrosine-223 and affecting downstream B-cell signaling pathways. Ibrutinib is a potent inhibitor of Btk (IC50=0.5 nM) and is efficacious in canine models of B-cell lymphoma. At dose ranges of 2.5–20 mg/kg, there was full occupancy of Btk in peripheral blood and tumor tissue for 24 h. A synthetic route to ibrutinib that employs Suzuki coupling of 3-iodo-1Hpyrazolo[3,4-d]pyrimidin-4-amine with (4-phenoxyphenyl)boronic acid followed by Mitsunobu reaction with N-Boc-3-hydroxypiperidine as key steps has been reported.

What is the Ibrutinib?

Ibrutinib is , while it's Molecular Formula is C 25 H 24 N 6 O 2 . Ibrutinib is a highly selective Bruton’s tyrosine kinase (Btk) irreversible inhibitor.

What is the CAS number for Ibrutinib?

The CAS number of Ibrutinib is 936563-96-1.

What is Ibrutinib (936563-96-1) used for?

In November 2013, the US FDA approved ibrutinib (also referred to as PCI-32765), for the treatment of patients with mantle cell lymphoma (MCL) who had received at least one prior therapy. Ibrutinib is the second oral agent approved for the treatment of MCL. It works by irreversibly inhibiting Bruton’s tyrosine kinase (Btk) leading to the inhibition of B-cell receptor signaling and resulting in the reduction of malignant B-cell proliferation and induction of cell death. Btk plays an important role in the differentiation, development, proliferation, and survival of B cells via activation of cell-cycle regulators and regulating the expression of pro- and antiapoptotic proteins. Aberrant Btk activity results in a variety of B-cell malignancies including MCL. Ibrutinib inhibits Btk by irreversibly binding to cysteine-481 in the active site thereby inhibiting phosphorylation of tyrosine-223 and affecting downstream B-cell signaling pathways. Ibrutinib is a potent inhibitor of Btk (IC50=0.5 nM) and is efficacious in canine models of B-cell lymphoma. At dose ranges of 2.5–20 mg/kg, there was full occupancy of Btk in peripheral blood and tumor tissue for 24 h. A synthetic route to ibrutinib that employs Suzuki coupling of 3-iodo-1Hpyrazolo[3,4-d]pyrimidin-4-amine with (4-phenoxyphenyl)boronic acid followed by Mitsunobu reaction with N-Boc-3-hydroxypiperidine as key steps has been reported.

Product classification

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936563-96-1

Product Name:Ibrutinib
Molecular Formula:C₂₅H₂₄N₆O₂
Molecular Weight:440.505

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Product Details

Purity:99%

Buy Good Quality Ibrutinib 936563-96-1 with a minimum purity of 99%

Molecular Formula:C₂₅H₂₄N₆O₂
Molecular Weight:440.505
Boiling Point:715.0±60.0 °C at 760 mmHg
PKA:4.09±0.30(Predicted)
Flash Point:386.2±32.9 °C
PSA：99.16000
Density:1.3±0.1 g/cm³
LogP:4.73640

936563-96-1 Relevant articles

A synthetic method of ibutinib

-

, (2022/03/02)

The present invention provides a prepara...

Preparation method of ibrutinib

-

, (2021/08/06)

The invention relates to a preparation m...

Preparation method of ibrutinib intermediate

-

, (2021/08/06)

The invention relates to a preparation m...

Purification method of ibrutinib crystal form A

-

Paragraph 0024-0026, (2021/08/07)

The invention discloses a purification m...

936563-96-1 Process route

: 330792-69-3
2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile

: 936563-87-0,936563-96-1,936563-97-2
ibrutinib

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrazine hydrate / methanol / 2 h / 25 - 30 °C 2.1: zinc(II) chloride / o-xylene / 20.17 h / 25 - 120 °C 3.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 25 - 30 °C 3.2: 3 h / 45 - 60 °C 4.1: sodium carbonate / dichloromethane; water / 10 - 15 °C 4.2: 0.33 h / -45 - 30 °C With sodium carbonate; hydrazine hydrate; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; o-xylene; water;
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / methanol / 2 h / 25 - 30 °C 2.1: zinc(II) chloride / o-xylene / 20.17 h / 25 - 120 °C 3.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 70 - 75 °C / Inert atmosphere 4.1: hydrogenchloride / ethyl acetate; isopropyl alcohol / 16 h / 25 - 30 °C 5.1: sodium carbonate / dichloromethane; water / 10 - 15 °C 5.2: 0.33 h / -45 - 30 °C With hydrogenchloride; sodium carbonate; caesium carbonate; hydrazine hydrate; zinc(II) chloride; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; o-xylene; water; ethyl acetate; isopropyl alcohol;
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / methanol / 2 h / 25 - 30 °C 2.1: zinc(II) chloride / o-xylene / 20.17 h / 25 - 120 °C 3.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 25 - 30 °C 3.2: 3 h / 45 - 60 °C 4.1: sodium carbonate / dichloromethane; water / 10 - 15 °C 4.2: 0.33 h / -45 - 30 °C 5.1: triethylamine; hydroquinone; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 25 - 30 °C With sodium carbonate; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; hydroquinone; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; o-xylene; water; acetonitrile;
Multi-step reaction with 6 steps 1.1: hydrazine hydrate / methanol / 2 h / 25 - 30 °C 2.1: zinc(II) chloride / o-xylene / 20.17 h / 25 - 120 °C 3.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 70 - 75 °C / Inert atmosphere 4.1: hydrogenchloride / ethyl acetate; isopropyl alcohol / 16 h / 25 - 30 °C 5.1: sodium carbonate / dichloromethane; water / 10 - 15 °C 5.2: 0.33 h / -45 - 30 °C 6.1: triethylamine; hydroquinone; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 25 - 30 °C With hydrogenchloride; sodium carbonate; caesium carbonate; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; hydroquinone; zinc(II) chloride; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; o-xylene; water; ethyl acetate; isopropyl alcohol; acetonitrile;
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / ethanol / 1 h / Reflux 2.1: 8 h / 150 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 21 - 22 °C 3.2: 14 h / 80 °C 4.1: hydrogenchloride / ethyl acetate / 0.5 h 5.1: triethylamine / dichloromethane With hydrogenchloride; potassium carbonate; hydrazine hydrate; triethylamine; In ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / ethanol / 1 h / Reflux 2.1: 8 h / 150 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 21 - 22 °C 3.2: 14 h / 80 °C 4.1: hydrogenchloride / ethyl acetate / 21 - 22 °C 5.1: triethylamine / methanol; tert-butyl methyl ether / -12 - -10 °C With hydrogenchloride; potassium carbonate; hydrazine hydrate; triethylamine; In methanol; ethanol; tert-butyl methyl ether; ethyl acetate; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps 1.1: triethylamine / ethanol / 1 h / 20 °C / Sonication 2.1: di-tert-butyl dicarbonate; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 2.2: 2.5 h / 180 °C 3.1: sodium hydroxide / methanol / 7 h / Inert atmosphere; Reflux 3.2: 1 h / 20 °C With di-tert-butyl dicarbonate; triethylamine; sodium hydroxide; In methanol; ethanol; dichloromethane;
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / toluene / 25 - 50 °C 2.1: 135 - 140 °C 3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran 3.2: 20 °C 4.1: trifluoroacetic acid / dichloromethane 5.1: triethylamine / tetrahydrofuran / 18 h / 25 - 30 °C With di-isopropyl azodicarboxylate; hydrazine hydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene; 3.1: \|Mitsunobu Displacement / 3.2: \|Mitsunobu Displacement;
Multi-step reaction with 3 steps 1.1: triethylamine / ethanol / 1 h / 20 °C / Sonication; Green chemistry 2.1: 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation; Green chemistry 3.1: sodium hydroxide; methanol / 7 h / Reflux; Green chemistry 3.2: 2 h / 20 °C / Green chemistry With methanol; triethylamine; sodium hydroxide; In ethanol;
Multi-step reaction with 5 steps 1.1: ethanol / 0.5 h / 5 °C 1.2: 15 h / 5 - 25 °C 2.1: butan-1-ol / 19 h / 120 °C 3.1: hydrogen / water; methanol / 2 h / 50 °C / 1034.32 Torr / Acidic conditions 4.1: sodium hydrogencarbonate / water; 2-methyltetrahydrofuran 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethyl acetate With hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 2-methyltetrahydrofuran; methanol; ethanol; water; ethyl acetate; butan-1-ol;

: 330792-69-3
2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile

: 936563-87-0,936563-96-1,936563-97-2
1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrazine hydrate / ethanol; water / 1 h / Heating 2.1: 4 h / 180 °C / Inert atmosphere 3.1: PS-triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C 4.1: hydrogenchloride / 1,4-dioxane / 1 h 4.2: 2 h With hydrogenchloride; PS-triphenylphosphine; di-isopropyl azodicarboxylate; hydrazine hydrate; In tetrahydrofuran; 1,4-dioxane; ethanol; water;
Multi-step reaction with 4 steps 1: triethylamine / methanol / 1 h / 50 °C 2: 5 h / 165 °C / Inert atmosphere 3: hydrogen bromide / acetic acid / 0.5 h / 0 °C 4: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C With hydrogen bromide; triethylamine; In methanol; dichloromethane; acetic acid;

Yield

Multi-step reaction with 4 steps

1.1: hydrazine hydrate / ethanol; water / 1 h / Heating

2.1: 4 h / 180 °C / Inert atmosphere

3.1: PS-triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C

4.1: hydrogenchloride / 1,4-dioxane / 1 h

4.2: 2 h

With hydrogenchloride; PS-triphenylphosphine; di-isopropyl azodicarboxylate; hydrazine hydrate; In tetrahydrofuran; 1,4-dioxane; ethanol; water;

Multi-step reaction with 4 steps

1: triethylamine / methanol / 1 h / 50 °C

2: 5 h / 165 °C / Inert atmosphere

3: hydrogen bromide / acetic acid / 0.5 h / 0 °C

4: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

With hydrogen bromide; triethylamine; In methanol; dichloromethane; acetic acid;

936563-96-1 Upstream products

814-68-6
acryloyl chloride
936563-86-9
tert-butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate
330792-69-3
2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile
330792-68-2
2-[hydroxy-(4-phenoxy-phenyl)-methylene]-malononitrile

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