(R)-Pioglitazone
Numéro de catalogue B8692418
Poids moléculaire: 356.4 g/mol
Clé InChI: HYAFETHFCAUJAY-QGZVFWFLSA-N
Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.
Patent
USRE036575
Procedure details
To a dimethylformamide solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g) was added palladium black (0.2 g) and catalytic reduction was carried out at 50° C. and 50 kg/cm2 for 5 hours. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was dissolved in 6N-hydrochloric acid and the solution was neutralized with sodium hydrogen carbonate to give 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as crystals. Yield: 650 mg (64.8%); m.p.: 173°-174° C.
Quantity
1 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>[Pd].CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
1 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1
|
|
Name
|
|
|
Quantity
|
0.2 g
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CN(C=O)C
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
was carried out at 50° C.
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The catalyst was filtered off
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
the filtrate was concentrated to dryness
|
DISSOLUTION
|
Type
|
DISSOLUTION
|
|
Details
|
The residue was dissolved in 6N-hydrochloric acid
|
Outcomes
Product
Details
Reaction Time |
5 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1
|
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
USRE036575
Procedure details
To a dimethylformamide solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g) was added palladium black (0.2 g) and catalytic reduction was carried out at 50° C. and 50 kg/cm2 for 5 hours. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was dissolved in 6N-hydrochloric acid and the solution was neutralized with sodium hydrogen carbonate to give 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as crystals. Yield: 650 mg (64.8%); m.p.: 173°-174° C.
Quantity
1 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>[Pd].CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
1 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1
|
|
Name
|
|
|
Quantity
|
0.2 g
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CN(C=O)C
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
was carried out at 50° C.
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The catalyst was filtered off
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
the filtrate was concentrated to dryness
|
DISSOLUTION
|
Type
|
DISSOLUTION
|
|
Details
|
The residue was dissolved in 6N-hydrochloric acid
|
Outcomes
Product
Details
Reaction Time |
5 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1
|
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
USRE036575
Procedure details
To a dimethylformamide solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g) was added palladium black (0.2 g) and catalytic reduction was carried out at 50° C. and 50 kg/cm2 for 5 hours. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was dissolved in 6N-hydrochloric acid and the solution was neutralized with sodium hydrogen carbonate to give 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as crystals. Yield: 650 mg (64.8%); m.p.: 173°-174° C.
Quantity
1 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>[Pd].CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
1 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1
|
|
Name
|
|
|
Quantity
|
0.2 g
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CN(C=O)C
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
was carried out at 50° C.
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The catalyst was filtered off
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
the filtrate was concentrated to dryness
|
DISSOLUTION
|
Type
|
DISSOLUTION
|
|
Details
|
The residue was dissolved in 6N-hydrochloric acid
|
Outcomes
Product
Details
Reaction Time |
5 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1
|
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. |
