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
US07563811B2
Procedure details
A suspension of 0.11 g of 3-(2-cyanophenyl)-5-(2-pyridyl)-2 (1H)-pyridone, 0.12 g of phenyl boronic acid 0.1 g of copper acetate and 0.3 ml of triethylamine in 10 ml of methylene chloride was stirred at room temperature for overnight. To this were added 5 ml of concentrated aqueous ammonia, 10 ml of water and 40 ml of ethyl acetate and the organic layer was separated, washed with water and a saturated saline solution and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:2) to give 0.06 g of the title product as pale yellow powder.
Name
3-(2-cyanophenyl)-5-(2-pyridyl)-2 (1H)-pyridone
Quantity
0.11 g
Type
reactant
Reaction Step One
Name
Identifiers
|
REACTION_CXSMILES
|
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:21])[NH:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.N>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:21])[N:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2] |f:5.6.7|
|
Inputs
Step One
|
Name
|
3-(2-cyanophenyl)-5-(2-pyridyl)-2 (1H)-pyridone
|
|
Quantity
|
0.11 g
|
|
Type
|
reactant
|
|
Smiles
|
C(#N)C1=C(C=CC=C1)C=1C(NC=C(C1)C1=NC=CC=C1)=O
|
|
Name
|
|
|
Quantity
|
0.12 g
|
|
Type
|
reactant
|
|
Smiles
|
C1(=CC=CC=C1)B(O)O
|
|
Name
|
|
|
Quantity
|
0.3 mL
|
|
Type
|
reactant
|
|
Smiles
|
C(C)N(CC)CC
|
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(Cl)Cl
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
catalyst
|
|
Smiles
|
C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-]
|
Step Two
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
reactant
|
|
Smiles
|
N
|
|
Name
|
|
|
Quantity
|
40 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(=O)OCC
|
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
was stirred at room temperature for overnight
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the organic layer was separated
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with water
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
a saturated saline solution and dried over magnesium sulfate
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The solvent was concentrated in vacuo
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:2)
|
Outcomes
Product
Details
Reaction Time |
8 (± 8) 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 | 0.06 g | |
| YIELD: CALCULATEDPERCENTYIELD | 42.7% |
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. |
