Nevirapine-D4
カタログ番号 B3026168
分子量: 270.32 g/mol
InChIキー: NQDJXKOVJZTUJA-CQOLUAMGSA-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
US05569760
Procedure details
The process according to claim 3, wherein 2-chloro-N-(2-chloro-4-methyl-3-pyridyl)-3-pyridine carboxamide is heated with cyclopropylamine in the presence of 0.5 to 2 mol of calcium oxide in an inert solvent to a temperature of 130° to 150° C. over a period of 5 to 8 hours, the reaction mixture is then cooled to a temperature below 40° C. and filtered, the filter cake is washed with an inert solvent and the combined filtrates are concentrated, the residue is then diluted with an inert solvent and this solution is added to a solution or suspension of a base in an inert solvent, heated at 120° to 150° C., the reaction mixture is then kept at a temperature of 120° to 150° C. for 30 to 90 minutes, the reaction medium is then distilled off as much as possible and the residue is hydrolysed at a temperature of 20° to 90° C., the hydrolysed residue is cooled down and mixed with an inert solvent and an organic acid and the mixture is stirred at a temperature of 5° to 50° C. for 30 to 90 minutes, the product is then present as a suspension which is isolated and washed with an inert solvent, followed by water and an alcohol to give nevirapine.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[C:12](Cl)=[N:13][CH:14]=[CH:15][C:16]=2[CH3:17])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[O-2].[Ca+2]>>[CH3:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:22]([CH:19]3[CH2:21][CH2:20]3)[C:2]3[N:3]=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=[O:9])[NH:10][C:11]=12 |f:2.3|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
ClC1=NC=CC=C1C(=O)NC=1C(=NC=CC1C)Cl
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C1(CC1)N
|
|
Name
|
|
|
Quantity
|
1.25 (± 0.75) mol
|
|
Type
|
reactant
|
|
Smiles
|
[O-2].[Ca+2]
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
an organic acid and the mixture is stirred at a temperature of 5° to 50° C. for 30 to 90 minutes
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
the reaction mixture is then cooled to a temperature below 40° C.
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
the filter cake is washed with an inert solvent
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
the combined filtrates are concentrated
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
the residue is then diluted with an inert solvent
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
this solution is added to a solution or suspension of a base in an inert solvent
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
heated at 120° to 150° C.
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
the reaction medium is then distilled off as much as possible and the residue
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
is hydrolysed at a temperature of 20° to 90° C.
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
the hydrolysed residue is cooled down
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
mixed with an inert solvent
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
present as a suspension which is isolated
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with an inert solvent
|
Outcomes
Product
Details
Reaction Time |
60 (± 30) min |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
|
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC=1C=CN=C2C1NC(=O)C=3C=CC=NC3N2C4CC4
|
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
US05569760
Procedure details
The process according to claim 3, wherein 2-chloro-N-(2-chloro-4-methyl-3-pyridyl)-3-pyridine carboxamide is heated with cyclopropylamine in the presence of 0.5 to 2 mol of calcium oxide in an inert solvent to a temperature of 130° to 150° C. over a period of 5 to 8 hours, the reaction mixture is then cooled to a temperature below 40° C. and filtered, the filter cake is washed with an inert solvent and the combined filtrates are concentrated, the residue is then diluted with an inert solvent and this solution is added to a solution or suspension of a base in an inert solvent, heated at 120° to 150° C., the reaction mixture is then kept at a temperature of 120° to 150° C. for 30 to 90 minutes, the reaction medium is then distilled off as much as possible and the residue is hydrolysed at a temperature of 20° to 90° C., the hydrolysed residue is cooled down and mixed with an inert solvent and an organic acid and the mixture is stirred at a temperature of 5° to 50° C. for 30 to 90 minutes, the product is then present as a suspension which is isolated and washed with an inert solvent, followed by water and an alcohol to give nevirapine.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[C:12](Cl)=[N:13][CH:14]=[CH:15][C:16]=2[CH3:17])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[O-2].[Ca+2]>>[CH3:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:22]([CH:19]3[CH2:21][CH2:20]3)[C:2]3[N:3]=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=[O:9])[NH:10][C:11]=12 |f:2.3|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
ClC1=NC=CC=C1C(=O)NC=1C(=NC=CC1C)Cl
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C1(CC1)N
|
|
Name
|
|
|
Quantity
|
1.25 (± 0.75) mol
|
|
Type
|
reactant
|
|
Smiles
|
[O-2].[Ca+2]
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
an organic acid and the mixture is stirred at a temperature of 5° to 50° C. for 30 to 90 minutes
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
the reaction mixture is then cooled to a temperature below 40° C.
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
the filter cake is washed with an inert solvent
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
the combined filtrates are concentrated
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
the residue is then diluted with an inert solvent
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
this solution is added to a solution or suspension of a base in an inert solvent
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
heated at 120° to 150° C.
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
the reaction medium is then distilled off as much as possible and the residue
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
is hydrolysed at a temperature of 20° to 90° C.
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
the hydrolysed residue is cooled down
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
mixed with an inert solvent
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
present as a suspension which is isolated
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with an inert solvent
|
Outcomes
Product
Details
Reaction Time |
60 (± 30) min |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
|
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC=1C=CN=C2C1NC(=O)C=3C=CC=NC3N2C4CC4
|
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. |
