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molecular formula C23H15N3O B3395873 Perampanel CAS No. 380917-97-5

Perampanel

Cat. No. B3395873
M. Wt: 349.4 g/mol
InChI Key: PRMWGUBFXWROHD-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07718807B2

Procedure details

A mixture of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate (4.73 g, 3.25 mmol) and ethanol (small amount) was concentrated under reduced pressure, followed by adding ethyl acetate (small amount) to the residue before further concentration under reduced pressure. A 25% HBr/acetic acid solution (1.04 g, 4.2 mmol) was added to an ethyl acetate (30 mL) suspension containing the resultant residue, which was then stirred at room temperature for 3.5 hours. The precipitated solid was collected by filtration, washed with ethyl acetate (small amount), and then dried under reduced pressure to provide 1.28 g of the title compound as pale yellow crystals.
Name
3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate
Quantity
4.73 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
1.04 g
Type
reactant
Reaction Step Two
Quantity
30 mL
Type
solvent
Reaction Step Two
[Compound]
Name
resultant residue
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
O.[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11](=[O:28])[N:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:15]=1)#[N:3].C(O)C.Br.C(O)(=O)C>C(OCC)(=O)C>[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11](=[O:28])[N:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:15]=1)#[N:3] |f:0.1,3.4|

Inputs

Step One
Name
3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate
Quantity
4.73 g
Type
reactant
Smiles
O.C(#N)C1=C(C=CC=C1)C=1C(N(C=C(C1)C1=NC=CC=C1)C1=CC=CC=C1)=O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)O
Step Two
Name
Quantity
1.04 g
Type
reactant
Smiles
Br.C(C)(=O)O
Name
Quantity
30 mL
Type
solvent
Smiles
C(C)(=O)OCC
Step Three
Name
resultant residue
Quantity
0 (± 1) mol
Type
reactant
Smiles

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
was then stirred at room temperature for 3.5 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CONCENTRATION
Type
CONCENTRATION
Details
was concentrated under reduced pressure
ADDITION
Type
ADDITION
Details
by adding ethyl acetate (small amount) to the residue
CONCENTRATION
Type
CONCENTRATION
Details
before further concentration under reduced pressure
FILTRATION
Type
FILTRATION
Details
The precipitated solid was collected by filtration
WASH
Type
WASH
Details
washed with ethyl acetate (small amount)
CUSTOM
Type
CUSTOM
Details
dried under reduced pressure

Outcomes

Product
Details
Reaction Time
3.5 h
Name
Type
product
Smiles
C(#N)C1=C(C=CC=C1)C=1C(N(C=C(C1)C1=NC=CC=C1)C1=CC=CC=C1)=O
Measurements
Type Value Analysis
AMOUNT: MASS 1.28 g
YIELD: CALCULATEDPERCENTYIELD 112.7%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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