Baricitinib

Base Information

• Chemical Name: Baricitinib
• CAS No.: 1187594-09-7
• Molecular Formula: C16H17N7O2S
• Molecular Weight: 371.423
• Hs Code.: 29350090
• Mol file: 1187594-09-7.mol

Synonyms:INCB 028050;LY 3009104;1-(Ethylsulfonyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-3-azetidineacetonitrile;

Chemical Property of Baricitinib

Chemical Property:

• PKA: 11.66±0.50(Predicted)
• PSA: 128.94000
• Density: 1.6±0.1 g/cm³
• LogP: 2.11438
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 30 mg/ml) or in DMF (up to 50 mg/ml).

Purity/Quality:

>95% ^*data from raw suppliers

Baricitinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Baricitinib (1187594-09-7), approved by the FDA for two inflammatory disorders, rheumatoid arthritis and alopecia areata, selectively inhibits Janus kinase 1 (IC50?= 5.9 nM) and 2 (5.7 nM), over 3 (0.56 μM).1?It thereby blocks JAK/STAT signaling, reducing cytokine release and suppressing the innate and adaptive immune systems.1,2?Was recently shown to significantly improve COVID-19 symptoms in a preliminary human trial, presumably through suppression of the cytokine release syndrome (“cytokine storm”) induced by SARS-CoV-2 infection.3
• Uses: Baricitinib is a JAK1 and JAK2 inhibitor and have been used as a promising treatment for rheumatoid arthritis.
• Clinical Use: Janus kinase inhibitor: Treatment of moderate to severe active rheumatoid arthritis
• Drug interactions: Potentially hazardous interactions with other drugs Avoid with other DMARDs due to increased immunosuppression. Use with care with other immunosuppressants. Antipsychotics: increased risk of agranulocytosis with clozapine - avoid. Live vaccines: avoid concomitant use

Technology Process of Baricitinib

There total 35 articles about Baricitinib 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: 99.0%

2-(1-(ethanesulfonyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-3-yl)acetonitrile (1919837-50-5) + 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → Baricitinib (1187594-09-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 80 - 85 ℃; for 5h;

Reference yield: 93.0%

tert-butyl 4-{1-[3-(cyanomethyl)-1-(ethylsulfonyl)azetidin-3-yl]-1H-pyrazol-4-yl}-7H-pyrrolo[2.3-d]pyrimidine-7-carboxylate → Baricitinib (1187594-09-7)

Guidance literature:

With hydrogenchloride; In ethanol; at 40 - 45 ℃;

Reference yield: 91.2%

2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile (1187595-85-2) + C14H15N5O2 → Baricitinib (1187594-09-7)

Guidance literature:

C₁₄H₁₅N₅O₂; With potassium carbonate; In acetonitrile; at 20 ℃; for 0.5h;

2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 40 ℃; for 8h;

upstream raw materials:

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

(4-{1-[3-(cyanomethyl)-1-(ethylsulphonyl)azetidin-3-yl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl 2,2-dimethylpropanoate

3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester

2-(1-(ethanesulfonyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-3-yl)acetonitrile

Downstream raw materials:

baricitinib phosphate