3-(4-Nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
Número de catálogo B194619
Peso molecular: 289.24 g/mol
Clave InChI: JKPJLYIGKKDZDT-UHFFFAOYSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
Patent
US08877932B2
Procedure details
Into a 5.0 L 4 necked RB flask, charged 100.0 g of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione, 10.0 g of 10% Pd/C and 3200 ml of DMF under nitrogen atmosphere. Stirred the mass and raise the reaction mass temperature to 60 -65° C. Started the hydrogen gas bubbling into reaction mass at temperature 60-65° C. for 6 hours. The progress of the reaction is monitored by TLC. Cooled the mass to temperature 25to 30° C. Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere and wash with dimethylformamide; wet Pd/C is transferred into a polythene bag for recovery. Distilled off the above organic layer solvent completely under vacuum below 60° C. Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min. Filtered the solid and wash with 200 mL of ethyl acetate (Lot-II). Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min. Dried Weight of the compound is 78.0 g.
[Compound]
Name
4
Quantity
5 L
Type
reactant
Reaction Step One
Quantity
100 g
Type
reactant
Reaction Step One
Name
Identifiers
|
REACTION_CXSMILES
|
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13])([O-])=O.[H][H]>[Pd].CN(C=O)C>[CH:11]1[CH:10]=[C:9]2[C:8](=[O:13])[N:7]([CH:14]3[C:15](=[O:21])[NH:16][C:17](=[O:20])[CH2:18][CH2:19]3)[CH2:6][C:5]2=[C:4]([NH2:1])[CH:12]=1
|
Inputs
Step One
[Compound]
|
Name
|
4
|
|
Quantity
|
5 L
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
100 g
|
|
Type
|
reactant
|
|
Smiles
|
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
|
|
Name
|
|
|
Quantity
|
10 g
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
|
Name
|
|
|
Quantity
|
3200 mL
|
|
Type
|
solvent
|
|
Smiles
|
CN(C)C=O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
30 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
Stirred the mass
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
raise the reaction mass temperature to 60 -65° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
bubbling into reaction mass at temperature 60-65° C. for 6 hours
|
|
Duration
|
6 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere
|
WASH
|
Type
|
WASH
|
|
Details
|
wash with dimethylformamide
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
Distilled off the above organic layer solvent completely under vacuum below 60° C
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min
|
|
Duration
|
60 min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
Filtered the solid
|
WASH
|
Type
|
WASH
|
|
Details
|
wash with 200 mL of ethyl acetate (Lot-II)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min
|
|
Duration
|
150 (± 30) min
|
Outcomes
Product
|
Name
|
|
|
Type
|
|
|
Smiles
|
C=1C=C2C(=C(C1)N)CN(C2=O)C3CCC(=O)NC3=O
|
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. |
Patent
US08877932B2
Procedure details
Into a 5.0 L 4 necked RB flask, charged 100.0 g of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione, 10.0 g of 10% Pd/C and 3200 ml of DMF under nitrogen atmosphere. Stirred the mass and raise the reaction mass temperature to 60 -65° C. Started the hydrogen gas bubbling into reaction mass at temperature 60-65° C. for 6 hours. The progress of the reaction is monitored by TLC. Cooled the mass to temperature 25to 30° C. Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere and wash with dimethylformamide; wet Pd/C is transferred into a polythene bag for recovery. Distilled off the above organic layer solvent completely under vacuum below 60° C. Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min. Filtered the solid and wash with 200 mL of ethyl acetate (Lot-II). Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min. Dried Weight of the compound is 78.0 g.
[Compound]
Name
4
Quantity
5 L
Type
reactant
Reaction Step One
Quantity
100 g
Type
reactant
Reaction Step One
Name
Identifiers
|
REACTION_CXSMILES
|
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13])([O-])=O.[H][H]>[Pd].CN(C=O)C>[CH:11]1[CH:10]=[C:9]2[C:8](=[O:13])[N:7]([CH:14]3[C:15](=[O:21])[NH:16][C:17](=[O:20])[CH2:18][CH2:19]3)[CH2:6][C:5]2=[C:4]([NH2:1])[CH:12]=1
|
Inputs
Step One
[Compound]
|
Name
|
4
|
|
Quantity
|
5 L
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
100 g
|
|
Type
|
reactant
|
|
Smiles
|
[N+](=O)([O-])C1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
|
|
Name
|
|
|
Quantity
|
10 g
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
|
Name
|
|
|
Quantity
|
3200 mL
|
|
Type
|
solvent
|
|
Smiles
|
CN(C)C=O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
30 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
Stirred the mass
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
raise the reaction mass temperature to 60 -65° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
bubbling into reaction mass at temperature 60-65° C. for 6 hours
|
|
Duration
|
6 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere
|
WASH
|
Type
|
WASH
|
|
Details
|
wash with dimethylformamide
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
Distilled off the above organic layer solvent completely under vacuum below 60° C
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min
|
|
Duration
|
60 min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
Filtered the solid
|
WASH
|
Type
|
WASH
|
|
Details
|
wash with 200 mL of ethyl acetate (Lot-II)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min
|
|
Duration
|
150 (± 30) min
|
Outcomes
Product
|
Name
|
|
|
Type
|
|
|
Smiles
|
C=1C=C2C(=C(C1)N)CN(C2=O)C3CCC(=O)NC3=O
|
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. |
