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molecular formula C15H14N4O B3026168 Nevirapine-D4 CAS No. 1051418-95-1

Nevirapine-D4

Cat. No. B3026168
M. Wt: 270.32 g/mol
InChI Key: NQDJXKOVJZTUJA-CQOLUAMGSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US05569760

Procedure details

The process according to claim 4, wherein 2-chloro-N-(2-chloro-4-methyl-3-pyridyl)-3-pyridine carboxamide is heated with cyclopropylamine in the presence of 1 to 2 mol of calcium oxide in diglyme to 135° to 145° C. for 6 to 7 hours, the reaction mixture is then cooled down to 20° to 30° C. and filtered, the filter cake is washed with diglyme and the combined filtrates are concentrated, the residue is then diluted with diglyme and this solution is added to a solution or suspension of sodium hydride in diglyme, heated to 130° to 140° C., and the reaction mixture is kept at a temperature of 130° to 140° C. for 30 minutes to one hour and then the reaction medium is distilled off, the residue is hydrolysed at a temperature of 50° to 80° C. and then cooled to a temperature of about 25° C. and mixed with an inert solvent and an organic acid and the reaction mixture is stirred for about 1 hour at 10° to 25° C., the resultant suspension of the product is separated, washed with an inert solvent, followed by water and alcohol to give nevirapine.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
1.5 (± 0.5) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

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]>COCCOCCOC>[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
1.5 (± 0.5) mol
Type
reactant
Smiles
[O-2].[Ca+2]
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
COCCOCCOC

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
25 °C
Stirring
Type
CUSTOM
Details
an organic acid and the reaction mixture is stirred for about 1 hour at 10° to 25° C.
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 down to 20° to 30° C.
FILTRATION
Type
FILTRATION
Details
filtered
WASH
Type
WASH
Details
the filter cake is washed with diglyme
CONCENTRATION
Type
CONCENTRATION
Details
the combined filtrates are concentrated
ADDITION
Type
ADDITION
Details
the residue is then diluted with diglyme
ADDITION
Type
ADDITION
Details
this solution is added to a solution or suspension of sodium hydride in diglyme
TEMPERATURE
Type
TEMPERATURE
Details
heated to 130° to 140° C.
WAIT
Type
WAIT
Details
the reaction mixture is kept at a temperature of 130° to 140° C. for 30 minutes to one hour
DISTILLATION
Type
DISTILLATION
Details
the reaction medium is distilled off
CUSTOM
Type
CUSTOM
Details
is hydrolysed at a temperature of 50° to 80° C.
ADDITION
Type
ADDITION
Details
mixed with an inert solvent
ADDITION
Type
ADDITION
Details
the resultant suspension of the product
CUSTOM
Type
CUSTOM
Details
is separated
WASH
Type
WASH
Details
washed with an inert solvent

Outcomes

Product
Details
Reaction Time
1 h
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 4, wherein 2-chloro-N-(2-chloro-4-methyl-3-pyridyl)-3-pyridine carboxamide is heated with cyclopropylamine in the presence of 1 to 2 mol of calcium oxide in diglyme to 135° to 145° C. for 6 to 7 hours, the reaction mixture is then cooled down to 20° to 30° C. and filtered, the filter cake is washed with diglyme and the combined filtrates are concentrated, the residue is then diluted with diglyme and this solution is added to a solution or suspension of sodium hydride in diglyme, heated to 130° to 140° C., and the reaction mixture is kept at a temperature of 130° to 140° C. for 30 minutes to one hour and then the reaction medium is distilled off, the residue is hydrolysed at a temperature of 50° to 80° C. and then cooled to a temperature of about 25° C. and mixed with an inert solvent and an organic acid and the reaction mixture is stirred for about 1 hour at 10° to 25° C., the resultant suspension of the product is separated, washed with an inert solvent, followed by water and alcohol to give nevirapine.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
1.5 (± 0.5) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

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]>COCCOCCOC>[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
1.5 (± 0.5) mol
Type
reactant
Smiles
[O-2].[Ca+2]
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
COCCOCCOC

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
25 °C
Stirring
Type
CUSTOM
Details
an organic acid and the reaction mixture is stirred for about 1 hour at 10° to 25° C.
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 down to 20° to 30° C.
FILTRATION
Type
FILTRATION
Details
filtered
WASH
Type
WASH
Details
the filter cake is washed with diglyme
CONCENTRATION
Type
CONCENTRATION
Details
the combined filtrates are concentrated
ADDITION
Type
ADDITION
Details
the residue is then diluted with diglyme
ADDITION
Type
ADDITION
Details
this solution is added to a solution or suspension of sodium hydride in diglyme
TEMPERATURE
Type
TEMPERATURE
Details
heated to 130° to 140° C.
WAIT
Type
WAIT
Details
the reaction mixture is kept at a temperature of 130° to 140° C. for 30 minutes to one hour
DISTILLATION
Type
DISTILLATION
Details
the reaction medium is distilled off
CUSTOM
Type
CUSTOM
Details
is hydrolysed at a temperature of 50° to 80° C.
ADDITION
Type
ADDITION
Details
mixed with an inert solvent
ADDITION
Type
ADDITION
Details
the resultant suspension of the product
CUSTOM
Type
CUSTOM
Details
is separated
WASH
Type
WASH
Details
washed with an inert solvent

Outcomes

Product
Details
Reaction Time
1 h
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.
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