Perampanel
货号 B3395873
分子量: 349.4 g/mol
InChI 键: PRMWGUBFXWROHD-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
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
[Compound]
Name
resultant residue
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
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
[Compound]
|
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. |
