Lenalidomide
Katalognummer B1683929
Molekulargewicht: 259.26 g/mol
InChI-Schlüssel: GOTYRUGSSMKFNF-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
Patent
US09085530B2
Procedure details
A mixture of 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-glutaric acid (5 g) and urea (1.08 g) in N,N-dimethylformamide (25 ml) was stirred and heated under reflux for 3˜4 hours. The reaction mixture concentrated under reduced pressure at 60° C. and then was added into ice water by being stirred rapidly. After filter, the cake was washed with isopropanol. The crude product was recrystallized from isopropanol and active carbon to give 1.4 g of off-white target compound. Yield: 30%. mp: 252.1˜254.3° C.
Name
3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-glutaric acid
Quantity
5 g
Type
reactant
Reaction Step One
Yield
30%
Identifiers
|
REACTION_CXSMILES
|
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]([CH2:17]C(O)=O)[CH2:13][C:14](O)=O)[C:6]2=[O:11].[NH2:21][C:22](N)=[O:23].CN(C)C=[O:28]>>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]1[CH2:13][CH2:14][C:22](=[O:23])[NH:21][C:17]1=[O:28])[C:6]2=[O:11]
|
Inputs
Step One
|
Name
|
3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-glutaric acid
|
|
Quantity
|
5 g
|
|
Type
|
reactant
|
|
Smiles
|
NC1=C2CN(C(C2=CC=C1)=O)C(CC(=O)O)CC(=O)O
|
|
Name
|
|
|
Quantity
|
1.08 g
|
|
Type
|
reactant
|
|
Smiles
|
NC(=O)N
|
|
Name
|
|
|
Quantity
|
25 mL
|
|
Type
|
reactant
|
|
Smiles
|
CN(C=O)C
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
was stirred
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
heated
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
under reflux for 3˜4 hours
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The reaction mixture concentrated under reduced pressure at 60° C.
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added into ice water
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
by being stirred rapidly
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
After filter
|
WASH
|
Type
|
WASH
|
|
Details
|
the cake was washed with isopropanol
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The crude product was recrystallized from isopropanol and active carbon
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 1.4 g | |
| YIELD: PERCENTYIELD | 30% |
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
US09085530B2
Procedure details
A mixture of 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-glutaric acid (5 g) and urea (1.08 g) in N,N-dimethylformamide (25 ml) was stirred and heated under reflux for 3˜4 hours. The reaction mixture concentrated under reduced pressure at 60° C. and then was added into ice water by being stirred rapidly. After filter, the cake was washed with isopropanol. The crude product was recrystallized from isopropanol and active carbon to give 1.4 g of off-white target compound. Yield: 30%. mp: 252.1˜254.3° C.
Name
3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-glutaric acid
Quantity
5 g
Type
reactant
Reaction Step One
Yield
30%
Identifiers
|
REACTION_CXSMILES
|
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]([CH2:17]C(O)=O)[CH2:13][C:14](O)=O)[C:6]2=[O:11].[NH2:21][C:22](N)=[O:23].CN(C)C=[O:28]>>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]1[CH2:13][CH2:14][C:22](=[O:23])[NH:21][C:17]1=[O:28])[C:6]2=[O:11]
|
Inputs
Step One
|
Name
|
3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-glutaric acid
|
|
Quantity
|
5 g
|
|
Type
|
reactant
|
|
Smiles
|
NC1=C2CN(C(C2=CC=C1)=O)C(CC(=O)O)CC(=O)O
|
|
Name
|
|
|
Quantity
|
1.08 g
|
|
Type
|
reactant
|
|
Smiles
|
NC(=O)N
|
|
Name
|
|
|
Quantity
|
25 mL
|
|
Type
|
reactant
|
|
Smiles
|
CN(C=O)C
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
was stirred
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
heated
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
under reflux for 3˜4 hours
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The reaction mixture concentrated under reduced pressure at 60° C.
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added into ice water
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
by being stirred rapidly
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
After filter
|
WASH
|
Type
|
WASH
|
|
Details
|
the cake was washed with isopropanol
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The crude product was recrystallized from isopropanol and active carbon
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 1.4 g | |
| YIELD: PERCENTYIELD | 30% |
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. |
