5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE Chemical Properties

Melting point:

71-75°C

Boiling point:

434.3±45.0 °C(Predicted)

Density 

1.221±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

10.85±0.10(Predicted)

form 

Solid

color 

White

InChI

InChI=1S/C10H8N2O/c13-10-5-4-8(7-12-10)9-3-1-2-6-11-9/h1-7H,(H,12,13)

InChIKey

NHWKTZWOSIVHOL-UHFFFAOYSA-N

SMILES

C1(C2C=CC(=O)NC=2)=NC=CC=C1

Safety Information

HS Code 

29333990

5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE Usage And Synthesis

Uses

5-(2-Pyridyl)-1,2-dihydropyridin-2-one is used in the synthesis of AMPA receptor antagonists in the treatment of neurological diseases causing dysfunction of glutamatergic neurotransmission.

Synthesis

The general procedure for the synthesis of [2,3'-bipyridin]-6'(1'H)-ones from 2-bromopyridine and 2-hydroxypyridine-5-boronic acid pinacol ester was carried out as follows: firstly, the synthesis of [2,3'-bipyridin]-6'(1'H)-one was carried out by Suzuki coupling reaction of 2-bromopyridine (18) with 6-hydroxypyridine-3-boronic acid pinacol ester catalyzed by Pd(PPh3)4, with Na2CO3 as the base and CH3CN/H2O ( 1/1) as solvent and reacted at 75 °C to afford intermediate 20 in 70% yield. Subsequently, intermediate 20 was converted to thio analog 21 in 71% yield by reaction with P2S5 in pyridine at 120 °C. Finally, intermediate 21 was alkylated with 2-methylbenzyl bromide in DMF in the presence of K2CO3 to give the target product 22 in 76% yield. This synthetic route is also suitable for the preparation of other analogs for assessing the effect of phenyl and pyridyl substituents on the pyridazine ring.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5774 - 5777
[2] Patent: WO2013/19938, 2013, A1. Location in patent: Page/Page column 34; 35

5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE(381233-78-9)Related Product Information

• 4-HYDROXYPYRIDINE
• 5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one
• 2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
• 5-Bromo-2-methoxypyridine
• 2,5-Dibromopyridine
• 2-(2-cyanophenyl)benzonitrile
• 2-Bromobenzonitrile
• 1-Phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one
• 3,5-Dimethoxypyridine
• Phenylboronic acid
• 2-Cyanophenylboronic acid
• PeraMpanel
• 3,5-Dibromopyridine
• 6'-Methoxy-2,3'-bipyridine
• PeraMpanel
• PRMWGUBFXWROHD-MYWHSQMISA-N
• 5'-(2-cyanophenyl)-6'-oxo-1'-phenyl-1',6'-dihydro-[2,3'-bipyridine] 1-oxide
• 4-(6'-oxo-1'-phenyl-1',6'-dihydro-[2,3'-bipyridin]-5'-yl)benzonitrile