| Identification | Back Directory | [Name]
5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE | [CAS]
381233-78-9 | [Synonyms]
Perampanel Impurity 1
5-(2-PYRIDYL)-2-PYRIDONE
[2,3'-BIPYRIDIN]-6'(1'H)-ONE
5-(2-Pyridyl)pyridin-2(1H)-one
5-pyridin-2-yl-1H-pyridin-2-one
2-Hydroxy-5-(2-pyridyl)pyridine
5-(Pyridin-2-yl)-2(1H)-pyridone
5-(Pyridin-2-yl)pyridin-2(1H)-one
5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE
5-(2-pyridyl)-1,2-dihydropyridine-2-one
5-(Pyridin-2-yl)-1,2-dihydropyridin-2-one | [EINECS(EC#)]
206-141-6 | [Molecular Formula]
C10H8N2O | [MDL Number]
MFCD11113414 | [MOL File]
381233-78-9.mol | [Molecular Weight]
172.19 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
10.85±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [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 |
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