Itacitinib

Base Information

• Chemical Name: Itacitinib
• CAS No.: 1334298-90-6
• Molecular Formula: C₂₆H₂₃F₄N₉O
• Molecular Weight: 553.522
• UNII: 19J3781LPM
• Wikidata: Q27891174
• NCI Thesaurus Code: C116855
• Pharos Ligand ID: KB4462SCAYZD
• Metabolomics Workbench ID: 153196
• ChEMBL ID: CHEMBL3622820
• Mol file: 1334298-90-6.mol

Synonyms:(1-(1-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)-4-piperidinyl)-3-(4-(1H-pyrrolo(2,3-d)pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-azetidinyl)acetonitrile;itacitinib

Chemical Property of Itacitinib

Chemical Property:

• PKA: 11.66±0.50(Predicted)
• PSA: 119.62000
• Density: 1.57±0.1 g/cm3(Predicted)
• LogP: 3.47948
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 553.19616904
• Heavy Atom Count: 40
• Complexity: 977

Purity/Quality:

98% min ^*data from raw suppliers

Itacitinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1N2CC(C2)(CC#N)N3C=C(C=N3)C4=C5C=CNC5=NC=N4)C(=O)C6=C(C(=NC=C6)C(F)(F)F)F
• Recent ClinicalTrials: Rollover Study to Provide Continued Treatment for Participants With B-Cell Malignancies Previously Enrolled in Studies of Parsaclisib (INCB050465)
• Recent EU Clinical Trials: The ABNL-MARRO 001 Study: A Phase 1/2 Study of Active Myeloid Target Compound Combinations in MDS/MPN Overlap Syndromes
• Recent NIPH Clinical Trials: Safety of Itacitinib in Combination With Corticosteroids for Treatment of Steroid-Naive Acute Graft-Versus-Host Disease in Japanese Subjects
• Uses: Itacitinib is an orally bioactive inhibitor of Janus-associated kinase 1 with potential antineoplastic activity.

Technology Process of Itacitinib

There total 45 articles about Itacitinib 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: 95.0%

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (96042-30-7) + 2-(1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)-3-hydrazineylazetidin-3-yl)acetonitrile → 2-(1-{1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl}-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile (1334298-90-6)

Guidance literature:

Reference yield: 93.5%

2-(1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile (1334303-20-6) → 2-(1-{1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl}-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile (1334298-90-6)

Guidance literature:

2-(1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile; With boron trifluoride diethyl etherate; In acetonitrile; at 5 - 20 ℃; for 23h;

With water; In acetonitrile; at 5 - 20 ℃; for 2h;

With ammonium hydroxide; In water; acetonitrile; at 5 - 20 ℃; for 20h;

Reference yield: 44.6%

2-(1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile + 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → 2-(1-{1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl}-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile (1334298-90-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; In 1,4-dioxane; water; at 85 ℃; Inert atmosphere;

upstream raw materials:

2-trifluoromethyl-3-fluoro-4-pyridinecarboxylic acid

2-(1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

4-(1H-pyrazol-4-yl)-7-((2-trimethylsilanylethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Downstream raw materials:

2-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)azetidin-3-yl)acetonitrile adipate

Refernces

• 1、 -. "PROCESSES AND INTERMEDIATES FOR MAKING A JAK INHIBITOR". . . Retrieved 2019/08/22.
• 2、 -. "PROCESSES AND INTERMEDIATES FOR MAKING A JAK INHIBITOR". . . Retrieved 2014/09/29.