1187595-85-2

Basic information

• Product Name: 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile
• 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;2-(1-ETHYLSULFONY)AZETIDIN-3-YLIDENE)ACETONITRILE;Acetonitrile, 2-[1-(ethylsulfonyl)-3-azetidinylidene]-;(1-Ethanesulfonyl-azetidin-3-ylidene)-acetonitrile;Baricitinib intermediates 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile
• CAS NO: 1187595-85-2
• Molecular Formula: C₇H₁₀N₂O₂S
• Molecular Weight: 186.2315
• Mol File: 1187595-85-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 360.8±52.0 °C(Predicted)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -8.49±0.20(Predicted)
• CAS DataBase Reference: 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile(1187595-85-2)
• EPA Substance Registry System: 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile(1187595-85-2)

Safety Data

• Hazardous Substances Data: 1187595-85-2(Hazardous Substances Data)

Usage

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.

Upstream product

• 1153949-11-1 3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester 
• 50586-62-4 diethyl cyanomethyl phosphonate 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 372-09-8 cyanoacetic acid 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 594-44-5 Ethanesulfonyl chloride 
• 1314910-43-4 2-(azetidin-3-ylidene)acetonitrile hydrochloride 
• 1379208-59-9 C₅H₇ClN₂*ClH 

Downstream Products

• 1187594-13-3 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 
• 1187595-90-9 (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 
• 1919837-50-5 2-(1-(ethanesulfonyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-3-yl)acetonitrile 
• 1187594-09-7 Baricitinib 

Relevant articles and documents

PYRAZOLYL PYRROLO[2,3-B]PYRMIDINE-5-CARBOXYLATE ANALOGS AND METHODS OF MAKING THE SAME

The present invention relates to new pyrrolopyridine compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibition of JAK1 and JAK3 kinase activity in a human or animal subject are also provided for the treatment diseases such as pruritus, alopecia, androgenetic alopecia, alopecia areata, vitiligo and psoriasis.

Preparation method of baricitinib

The invention discloses a preparation method of baricitinib and belongs to the technical field of drug preparation. The method comprises that 4-chloropyrrolopyrimidine as a starting raw material is subjected to amino protection, the product, hydrazine hydrate and acrolein undergo a one-pot displacement reaction and a cyclization reaction to produce an intermediate 4, a starting raw material 1, 3-dibromoacetone and ethylene glycol undergo a condensation reaction to produce an intermediate 5, the intermediate 5 and ethyl sulfonamide undergo a condensation reaction to produce an intermediate 6, the intermediate 6 and diethyl cyanomethylphosphonate undergo a reaction under action of a strong base to produce an intermediate 7, the intermediate 4 and the intermediate 7 undergo an addition reaction under the action of a catalyst, and the product undergoes a deprotection reaction to produce a desired product 1. The preparation method needs mild reaction conditions. The intermediate purification method is simple and easy, has a total yield of 40-55% and is suitable for industrial production.

New synthesis methods of JCK inhibitor baricitinib and intermediate thereof

The present invention provides a new synthesis method of a baricitinib compound 11. According to the present invention, by using a compound 1 as a staring raw material, the amino group is protected by directly using ethanesulfonyl chloride, and direct cyclization is directly performed by using the effect of an alkali to obtain a key intermediate compound 3 so as to avoid the use of other protection groups and substantially improve the route efficiency and the atomic economy; during the compound 5 preparation, a Wittig reaction is performed by using triphenylphosphine acetonitrile so as to avoid the use of strong alkali and improve the reaction yield; the completely-new neopentyl glycol borate derivative compound 8 has good stability and good crystallinity so as to simplify the separation and purification process; and the route is simple to operate and has the high yield, the purity of the obtained product is high, and the synthesis method is suitable for amplification production. The formulas 1-11 are defined in the specification.