Risperidone-D5
カタログ番号 B2424515
分子量: 415.524
InChIキー: RAPZEAPATHNIPO-SGEUAGPISA-N
注意: 研究専用です。人間または獣医用ではありません。
Patent
US06750341B2
Procedure details
Isopropanol (20 mL), 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Compound II)(“the chlorine derivative”)(2.63 g, 10 mmoles, 1 eq.), 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (Compound I)(“the piperidine derivative”) (2.17 g, 10 mmoles, 1 eq.), sodium carbonate (3.18 g, 30 mmoles, 3 eq.), and potassium iodide (66 mg) were added to a 100 mL round bottom flask and stirred with a magnetic stir bar. The flask was placed in an oil bath at 80° C. and allowed to reflux for 9 hours. The flask was then cooled in an ice bath and the contents was filtered. The filter cake was washed in the filter with a small amount of isopropanol. The filter cake was then slurried 3 times in 20 mL of water and filtered. The resulting slurry was dried to give 3 g of material in 73% yield. The slurry was recrystallized by dissolving in 37 mL of boiling isopropanol, filtered hot and allowed to cool and filtered to give material which had a purity of 99.7% and an overall yield of 60%.
Quantity
2.63 g
Type
reactant
Reaction Step One
Name
Yield
73%
Identifiers
|
REACTION_CXSMILES
|
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]=1[CH3:15].[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].C(O)(C)C>[CH3:15][C:5]1[N:6]=[C:7]2[N:8]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:10])[C:4]=1[CH2:3][CH2:2][N:27]1[CH2:26][CH2:25][CH:24]([C:21]2[C:20]3[CH:30]=[CH:31][C:17]([F:16])=[CH:18][C:19]=3[O:23][N:22]=2)[CH2:29][CH2:28]1 |f:2.3.4,5.6|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
2.63 g
|
|
Type
|
reactant
|
|
Smiles
|
ClCCC1=C(N=C2N(C1=O)CCCC2)C
|
|
Name
|
|
|
Quantity
|
2.17 g
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
|
|
Name
|
|
|
Quantity
|
3.18 g
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
|
Name
|
|
|
Quantity
|
66 mg
|
|
Type
|
catalyst
|
|
Smiles
|
[I-].[K+]
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(C)O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
stirred with a magnetic stir bar
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The flask was placed in an oil bath at 80° C.
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux for 9 hours
|
|
Duration
|
9 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The flask was then cooled in an ice bath
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the contents was filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
The filter cake was washed in the
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filter with a small amount of isopropanol
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The resulting slurry was dried
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC1=C(C(=O)N2CCCCC2=N1)CCN3CCC(CC3)C=4C=5C=CC(=CC5ON4)F
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 3 g | |
| YIELD: PERCENTYIELD | 73% | |
| YIELD: CALCULATEDPERCENTYIELD | 73.1% |
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
US06750341B2
Procedure details
Isopropanol (20 mL), 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Compound II)(“the chlorine derivative”)(2.63 g, 10 mmoles, 1 eq.), 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (Compound I)(“the piperidine derivative”) (2.17 g, 10 mmoles, 1 eq.), sodium carbonate (3.18 g, 30 mmoles, 3 eq.), and potassium iodide (66 mg) were added to a 100 mL round bottom flask and stirred with a magnetic stir bar. The flask was placed in an oil bath at 80° C. and allowed to reflux for 9 hours. The flask was then cooled in an ice bath and the contents was filtered. The filter cake was washed in the filter with a small amount of isopropanol. The filter cake was then slurried 3 times in 20 mL of water and filtered. The resulting slurry was dried to give 3 g of material in 73% yield. The slurry was recrystallized by dissolving in 37 mL of boiling isopropanol, filtered hot and allowed to cool and filtered to give material which had a purity of 99.7% and an overall yield of 60%.
Quantity
2.63 g
Type
reactant
Reaction Step One
Name
Yield
73%
Identifiers
|
REACTION_CXSMILES
|
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]=1[CH3:15].[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].C(O)(C)C>[CH3:15][C:5]1[N:6]=[C:7]2[N:8]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:10])[C:4]=1[CH2:3][CH2:2][N:27]1[CH2:26][CH2:25][CH:24]([C:21]2[C:20]3[CH:30]=[CH:31][C:17]([F:16])=[CH:18][C:19]=3[O:23][N:22]=2)[CH2:29][CH2:28]1 |f:2.3.4,5.6|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
2.63 g
|
|
Type
|
reactant
|
|
Smiles
|
ClCCC1=C(N=C2N(C1=O)CCCC2)C
|
|
Name
|
|
|
Quantity
|
2.17 g
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
|
|
Name
|
|
|
Quantity
|
3.18 g
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
|
Name
|
|
|
Quantity
|
66 mg
|
|
Type
|
catalyst
|
|
Smiles
|
[I-].[K+]
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(C)O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
stirred with a magnetic stir bar
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The flask was placed in an oil bath at 80° C.
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux for 9 hours
|
|
Duration
|
9 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The flask was then cooled in an ice bath
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the contents was filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
The filter cake was washed in the
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filter with a small amount of isopropanol
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The resulting slurry was dried
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC1=C(C(=O)N2CCCCC2=N1)CCN3CCC(CC3)C=4C=5C=CC(=CC5ON4)F
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 3 g | |
| YIELD: PERCENTYIELD | 73% | |
| YIELD: CALCULATEDPERCENTYIELD | 73.1% |
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
US06750341B2
Procedure details
Isopropanol (20 mL), 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Compound II)(“the chlorine derivative”)(2.63 g, 10 mmoles, 1 eq.), 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (Compound I)(“the piperidine derivative”) (2.17 g, 10 mmoles, 1 eq.), sodium carbonate (3.18 g, 30 mmoles, 3 eq.), and potassium iodide (66 mg) were added to a 100 mL round bottom flask and stirred with a magnetic stir bar. The flask was placed in an oil bath at 80° C. and allowed to reflux for 9 hours. The flask was then cooled in an ice bath and the contents was filtered. The filter cake was washed in the filter with a small amount of isopropanol. The filter cake was then slurried 3 times in 20 mL of water and filtered. The resulting slurry was dried to give 3 g of material in 73% yield. The slurry was recrystallized by dissolving in 37 mL of boiling isopropanol, filtered hot and allowed to cool and filtered to give material which had a purity of 99.7% and an overall yield of 60%.
Quantity
2.63 g
Type
reactant
Reaction Step One
Name
Yield
73%
Identifiers
|
REACTION_CXSMILES
|
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]=1[CH3:15].[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].C(O)(C)C>[CH3:15][C:5]1[N:6]=[C:7]2[N:8]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:10])[C:4]=1[CH2:3][CH2:2][N:27]1[CH2:26][CH2:25][CH:24]([C:21]2[C:20]3[CH:30]=[CH:31][C:17]([F:16])=[CH:18][C:19]=3[O:23][N:22]=2)[CH2:29][CH2:28]1 |f:2.3.4,5.6|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
2.63 g
|
|
Type
|
reactant
|
|
Smiles
|
ClCCC1=C(N=C2N(C1=O)CCCC2)C
|
|
Name
|
|
|
Quantity
|
2.17 g
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1
|
|
Name
|
|
|
Quantity
|
3.18 g
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
|
Name
|
|
|
Quantity
|
66 mg
|
|
Type
|
catalyst
|
|
Smiles
|
[I-].[K+]
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(C)O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
stirred with a magnetic stir bar
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The flask was placed in an oil bath at 80° C.
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux for 9 hours
|
|
Duration
|
9 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The flask was then cooled in an ice bath
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the contents was filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
The filter cake was washed in the
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filter with a small amount of isopropanol
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The resulting slurry was dried
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC1=C(C(=O)N2CCCCC2=N1)CCN3CCC(CC3)C=4C=5C=CC(=CC5ON4)F
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 3 g | |
| YIELD: PERCENTYIELD | 73% | |
| YIELD: CALCULATEDPERCENTYIELD | 73.1% |
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. |
