2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile

Base Information

• Chemical Name: 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile
• CAS No.: 1187595-85-2
• Molecular Formula: C7H10N2O2S
• Molecular Weight: 186.235
• Hs Code.: 2933998090
• Mol file: 1187595-85-2.mol

Synonyms:2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile;2-[1-(Ethylsulfonyl)-3-azetidinylidene]acetonitrile;[1-(ethylsulfonyl)azetidin-3-ylidene]acetonitrile;2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile

Chemical Property of 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile

Chemical Property:

• Boiling Point: 360.8±52.0 °C(Predicted)
• PKA: -8.49±0.20(Predicted)
• PSA: 69.55000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 1.12038
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

2-(1-(Ethylsulfonyl)azetidin-3-ylidene)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-(1-(Ethylsulfonyl)azetidin-3-ylidene)acetonitrile is an intermediate in the synthesis of Baricitinib, a JAK 1 and 2 inhibitor used in the treatment of rheumatoid arthritis.

Technology Process of 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile

There total 10 articles about 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile 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: 98.59%

2-(azetidin-3-ylidene)acetonitrile hydrochloride (1314910-43-4) + Ethanesulfonyl chloride (594-44-5) → 2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile (1187595-85-2)

Guidance literature:

2-(azetidin-3-ylidene)acetonitrile hydrochloride; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 10 ℃; for 0.166667h;

Ethanesulfonyl chloride; In acetonitrile; at 0 - 25 ℃; for 16h;

Reference yield: 96.4%

diethyl cyanomethyl phosphonate (50586-62-4) + 1-(ethylsulfonyl)azetidin-3-one → 2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile (1187595-85-2)

Guidance literature:

diethyl cyanomethyl phosphonate; With sodium methylate; In tetrahydrofuran; at 10 - 20 ℃; for 0.75h; Inert atmosphere;

1-(ethylsulfonyl)azetidin-3-one; In tetrahydrofuran; at 30 ℃; for 11h;

Reference yield: 81.0%

1-(ethylsulfonyl)azetidin-3-one + cyanoacetic acid (372-09-8) → 2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile (1187595-85-2)

Guidance literature:

With piperidine; In toluene; Reflux;

upstream raw materials:

2-(azetidin-3-ylidene)acetonitrile hydrochloride

Ethanesulfonyl chloride

C₅H₇ClN₂*ClH

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

Downstream 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

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

Baricitinib

(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

Refernces

• 1、 -. "JAK INHIBITORS". . . Retrieved 2018/05/03.
• 2、 -. "Preparation method of baricitinib". Paragraph 0054; 0062; 0063. . Retrieved 2018/07/06.