PF 06465469 Discontinued See A191400

Base Information

• Chemical Name: PF 06465469 Discontinued See A191400
• CAS No.: 1407966-77-1
• Molecular Formula: C₃₀H₃₃N₇O₂
• Molecular Weight: 523.638
• Mol file: 1407966-77-1.mol

Synonyms:

Chemical Property of PF 06465469 Discontinued See A191400

Chemical Property:

• Melting Point: 209-212°C
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble5mg/mL, clear

Purity/Quality:

≥95% by HPLC ^*data from raw suppliers

(R)-3-[1-(1-Acryloylpiperidin-3-yl)-4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-N-(4-isopropyl-5-methylphenyl)benzamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

Useful:

• Uses: PF 06465469 is a covalent Inhibitors of Interleukin-2 Inducible T Cell Kinase (Itk) with nanomolar potency in a whole-blood assay. (R)-3-[1-(1-Acryloylpiperidin-3-yl)-4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-N-(4-isopropyl-5-methylphenyl)benzamide is a potential covalent inhibitor of Interleukin-2 Inducible T Cell KInase (Itk). Itk is a member of the TEC-kinase family and is associated with the induction of T cell proliferation and drives cytokines through NFATc.

Technology Process of PF 06465469 Discontinued See A191400

There total 7 articles about PF 06465469 Discontinued See A191400 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:

C27H31N7O*ClH + acryloyl chloride (814-68-6,25189-84-8) → PF-06465469 (1407966-77-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1021/jm301190s

Reference yield:

C32H39N7O3 → PF-06465469 (1407966-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane / 0 - 25 °C

2: triethylamine / dichloromethane / 0 °C

With hydrogenchloride; triethylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm301190s

Reference yield:

(R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylic acid tert-butyl ester (1276110-38-3) → PF-06465469 (1407966-77-1)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 120 °C

2: sodium hydroxide; water / methanol

3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 160 °C

4: hydrogenchloride / 1,4-dioxane / 0 - 25 °C

5: triethylamine / dichloromethane / 0 °C

With hydrogenchloride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; water; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 1: |Suzuki Coupling;

DOI:10.1021/jm301190s

upstream raw materials:

C₂₂H₂₆N₆O₄

(R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylic acid tert-butyl ester

acryloyl chloride

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

Refernces