1153949-11-1

Basic information

• Product Name: 1-Boc-3-(cyanomethylene)azetidine
• Synonyms: 1-Boc-3-(cyanomethylene)azetidine;3-Cyanomethylene-azetidine-1-carboxylic acid tert-butyl ester;tert-butyl 3-(cyanoMethylene)azetidine-1-carboxylate;tert-butyl 3-(cyanoMethylidene)azetidine-1-carboxylate;3-(Cyanomethylene)-1-azetidinecarboxylic acid tert-butyl ester;P-Hydroxy phenyl butanone (Raspberry ketone);1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine;tert-Butyl 3-(cyanomethylene)
• CAS NO: 1153949-11-1
• Molecular Formula: C₁₀H₁₄N₂O₂
• Molecular Weight: 194.23036
• Mol File: 1153949-11-1.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 309.7±35.0 °C(Predicted)
• Appearance: /
• Density: 1.215
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.88±0.20(Predicted)
• CAS DataBase Reference: 1-Boc-3-(cyanomethylene)azetidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-3-(cyanomethylene)azetidine(1153949-11-1)
• EPA Substance Registry System: 1-Boc-3-(cyanomethylene)azetidine(1153949-11-1)

Safety Data

• RIDADR: UN 3439 6.1/PG III
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1153949-11-1(Hazardous Substances Data)

Usage

Uses

1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine is used in the synthesis of baricitinib via Horner-Emmons reaction of tert-butyl-oxoazetidine-carboxylate followed by sulfonamidation, nucleophilic addition. and subsequent Suzuki-coupling reaction.

InChI:InChI=1S/C10H14N2O2/c1-10(2,3)14-9(13)12-6-8(7-12)4-5-11/h4H,6-7H2,1-3H3

Upstream product

• 398489-26-4 tert-butyl 3-oxoazetidine-1-carboxylate 
• 15898-47-2 (cyanomethyl)triphenylphosphonium bromide 
• 50586-62-4 diethyl cyanomethyl phosphonate 
• 141699-55-0 tert-butyl 3-hydroxyazetidine-1-carboxylate 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 

Downstream Products

• 1153949-15-5 tert-butyl 3-(cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate 
• 1334298-90-6 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 
• 1334302-63-4 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 

Relevant articles and documents

An efficient synthesis of baricitinib

A highly efficient method for the synthesis of baricitinib was developed. The starting material tert-butyl 3-oxoazetidine-1-carboxylate was converted to intermediate 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile via the Horner-Emmons reaction, deprotection of the N-Boc-group and a final sulfonamidation reaction. Then the nucleophilic addition reaction was carried out smoothly to afford the borate intermediate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene under reflux. Finally, the desired compound baricitinib was obtained by the Suzuki coupling reaction of 4-chloro-7-H-pyrrolo[2,3-d]pyrimidine with the above borate intermediate. All compounds were characterised by IR, MS, 1H NMR and 13C NMR. The overall yield in this synthetic route was as high as 49%. Moreover, this procedure is straightforward to carry out, has low cost and is suitable for industrial production.

SUBSTITUTED 1H-IMIDAZO[1, 2-B]PYRAZOLE-3-CARBOXAMIDE AS BRUTON TYROSINE KINASE INHIBITORS

This invention relates to a series of compounds 1H-imidazo [1, 2-b] pyrazole-3-carboxamide substituted represented by formula I used as kinase inhibitors, in particular BTK inhibitors (Bruton tyrosine kinase), and the methods of manufacture and use thereof for the treatment of an autoimmune disease, inflammatory disease, cancer and potentially allergies.

Compounds serving as IRAK inhibitors and preparation method and application thereof

The invention belongs to the field of IRAK inhibitors, and particularly relates to compounds shown in a formula (I) and applicable to treating cancers and inflammatory diseases related to interleukin-1 receptor-associated kinase (IRAK). Experiments show t