1-METHYL-4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORALAN-2-YL)PYRIDINE-2-YL]PIPERAZINE Chemical Properties

Melting point:

125 °C

Boiling point:

435.2±45.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

8.41±0.31(Predicted)

form 

solid

color 

white

InChI

InChI=1S/C16H26BN3O2/c1-15(2)16(3,4)22-17(21-15)13-6-7-14(18-12-13)20-10-8-19(5)9-11-20/h6-7,12H,8-11H2,1-5H3

InChIKey

KVQXFNGVIIPCSX-UHFFFAOYSA-N

SMILES

N1(C)CCN(C2=NC=C(B3OC(C)(C)C(C)(C)O3)C=C2)CC1

Safety Information

Hazard Codes 

C

Risk Statements 

22-34

Safety Statements 

22-26-36/37/39-45

RIDADR 

UN2811

TSCA 

No

HazardClass 

6.1

HS Code 

2933998090

1-METHYL-4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORALAN-2-YL)PYRIDINE-2-YL]PIPERAZINE Usage And Synthesis

Uses

1-Methyl-4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl]piperazine is used to prepare yrazolopyridine and indazoles as histone lysine methyltransferase EZH2 inhibitors. It is also used to synthesize tetrahydropyrido pyrazines as anaplastic lymphoma kinase inhibitors.

Synthesis

Using 1-(5-bromopyridin-2-yl)-4-methylpiperazine (1.5 g, 5.9 mmol), bis(pinacolato)diboron (1.6 g, 6.5 mmol), potassium acetate (1.8 g, 18 mmol), and Pd(dppf)2Cl2[CH2Cl2] (0.73 g, 0.89 mmol) as raw materials, the mixture was dissolved under nitrogen protection in DMSO (20 mL) and the reaction was stirred at 80 °C overnight. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate (EA). The organic phases were combined and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, v/v=3 to pure ethyl acetate) to afford the target product, 6-(4-methyl-1-piperazinyl)pyridine-3-boronic acid pinacol ester (1.0 g, 56% yield) as a brown solid. Mass spectrometry (MS) analysis showed m/z 304 (M+H)+.

References

[1] Patent: WO2016/73956, 2016, A1. Location in patent: Paragraph 00361
[2] Patent: EP2719697, 2014, A1. Location in patent: Paragraph 0169; 0172; 0173

1-METHYL-4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORALAN-2-YL)PYRIDINE-2-YL]PIPERAZINE(918524-63-7)Related Product Information

• 6-(4-MorpholinylMethyl)pyridine-3-boronic acid pinacol ester
• Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
• 2-(BENZYLAMINO)PYRIDINE-5-BORONIC ACID PINACOL ESTER
• 6-(CYCLOHEXYLAMINO)PYRIDINE-3-BORONIC ACID PINACOL ESTER
• 6-(4-FLUOROPHENYL)PYRIDINE-3-BORONIC ACID PINACOL ESTER
• TERT-BUTYL N-METHYL-N-[5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDIN-2-YL]CARBAMATE
• 2-(4-METHYLBENZYLAMINO)PYRIDINE-5-BORONIC ACID PINACOL ESTER
• 4-[5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDIN-2-YL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• TERT-BUTYL N-METHYL-N-[3-METHYL-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDIN-2-YL]CARBAMATE
• 2-(CYCLOPROPYLMETHOXY)-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE-2-CARBOXYLIC ACID DIETHYLAMIDE
• N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide
• 2-CYANOPYRIDINE-4-BORONIC ACID PINACOL ESTER
• 6-FLUOROPYRIDINE-2-BORONIC ACID PINACOL ESTER
• 1-(5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDIN-2-YL)PIPERAZINE
• 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)chroman, 97%
• 6-Dimethylaminopyridine-3-boronic acid pinacol ester
• 2-METHYLSULFANYL-5-(4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLAN-2-YL)PYRIDINE