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molecular formula C14H14ClF5N4O2S B8278460 4-(2-Chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one

4-(2-Chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one

Cat. No. B8278460
M. Wt: 432.8 g/mol
InChI Key: DCXFIOLWWRXEQH-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08822508B2

Procedure details

To a hot solution (80° C.) of ZnCl2 (0.23 g, 1.69 mmol, 10 mol %) and 2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole a28 (4 g, 16.96 mmol) in dioxane (200 ml) is added a solution of 4-(2-chloro-2,2-difluoroethyl)-1-(chloromethyl)pyrrolidin-2-one a18 in dioxane (5 ml). The reaction mixture is heated at 85° C. for 5 days, then a further 2 g of pyrrolidinone a18 is added in one portion and the reaction mixture is kept under agitation at 90° C. for 1 day. A further addition of pyrrolidinone a18 (2 g) in order to insure complete conversion of compound a28 and further heating of the reaction mixture at reflux for 3 days increased significatively the conversion of imidazo[2,1-b][1,3,4]thiadiazole a28. After cooling and hydrolysis (250 ml of water), the crude mixture is extracted by CH2Cl2 (2×250 ml). The cumulated organic layers are dried over MgSO4, filtered and condensed under reduced pressure. The residue is purified over silicagel (eluent: CH2Cl2/MeOH/NH4OH 99/1/0.1) to afford 4-(2-chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one 4.
Quantity
2 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
200 mL
Type
solvent
Reaction Step Four
Quantity
5 mL
Type
solvent
Reaction Step Four
Name
Quantity
0.23 g
Type
catalyst
Reaction Step Four
Name
Quantity
250 mL
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][CH2:3][C:4]1[S:8][C:7]2=[N:9][C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][N:6]2[N:5]=1.[Cl:16][C:17]([F:28])([F:27])[CH2:18][CH:19]1[CH2:23][N:22]([CH2:24]Cl)[C:21](=[O:26])[CH2:20]1.N1CCCC1=O.S1C=NN2C=CN=C12>O1CCOCC1.[Cl-].[Cl-].[Zn+2].O>[Cl:16][C:17]([F:27])([F:28])[CH2:18][CH:19]1[CH2:23][N:22]([CH2:24][C:11]2[N:6]3[C:7]([S:8][C:4]([CH2:3][O:2][CH3:1])=[N:5]3)=[N:9][C:10]=2[C:12]([F:15])([F:13])[F:14])[C:21](=[O:26])[CH2:20]1 |f:5.6.7|

Inputs

Step One
Name
Quantity
2 g
Type
reactant
Smiles
N1C(CCC1)=O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
N1C(CCC1)=O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
S1C=2N(N=C1)C=CN2
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
COCC1=NN2C(S1)=NC(=C2)C(F)(F)F
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC(CC1CC(N(C1)CCl)=O)(F)F
Name
Quantity
200 mL
Type
solvent
Smiles
O1CCOCC1
Name
Quantity
5 mL
Type
solvent
Smiles
O1CCOCC1
Name
Quantity
0.23 g
Type
catalyst
Smiles
[Cl-].[Cl-].[Zn+2]
Step Five
Name
Quantity
250 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
85 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
further heating of the reaction mixture
TEMPERATURE
Type
TEMPERATURE
Details
at reflux for 3 days
Duration
3 d
TEMPERATURE
Type
TEMPERATURE
Details
After cooling
EXTRACTION
Type
EXTRACTION
Details
the crude mixture is extracted by CH2Cl2 (2×250 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The cumulated organic layers are dried over MgSO4
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
condensed under reduced pressure
CUSTOM
Type
CUSTOM
Details
The residue is purified over silicagel (eluent: CH2Cl2/MeOH/NH4OH 99/1/0.1)

Outcomes

Product
Details
Reaction Time
1 d
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 74%

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
US08822508B2

Procedure details

To a hot solution (80° C.) of ZnCl2 (0.23 g, 1.69 mmol, 10 mol %) and 2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole a28 (4 g, 16.96 mmol) in dioxane (200 ml) is added a solution of 4-(2-chloro-2,2-difluoroethyl)-1-(chloromethyl)pyrrolidin-2-one a18 in dioxane (5 ml). The reaction mixture is heated at 85° C. for 5 days, then a further 2 g of pyrrolidinone a18 is added in one portion and the reaction mixture is kept under agitation at 90° C. for 1 day. A further addition of pyrrolidinone a18 (2 g) in order to insure complete conversion of compound a28 and further heating of the reaction mixture at reflux for 3 days increased significatively the conversion of imidazo[2,1-b][1,3,4]thiadiazole a28. After cooling and hydrolysis (250 ml of water), the crude mixture is extracted by CH2Cl2 (2×250 ml). The cumulated organic layers are dried over MgSO4, filtered and condensed under reduced pressure. The residue is purified over silicagel (eluent: CH2Cl2/MeOH/NH4OH 99/1/0.1) to afford 4-(2-chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one 4.
Quantity
2 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
200 mL
Type
solvent
Reaction Step Four
Quantity
5 mL
Type
solvent
Reaction Step Four
Name
Quantity
0.23 g
Type
catalyst
Reaction Step Four
Name
Quantity
250 mL
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][CH2:3][C:4]1[S:8][C:7]2=[N:9][C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][N:6]2[N:5]=1.[Cl:16][C:17]([F:28])([F:27])[CH2:18][CH:19]1[CH2:23][N:22]([CH2:24]Cl)[C:21](=[O:26])[CH2:20]1.N1CCCC1=O.S1C=NN2C=CN=C12>O1CCOCC1.[Cl-].[Cl-].[Zn+2].O>[Cl:16][C:17]([F:27])([F:28])[CH2:18][CH:19]1[CH2:23][N:22]([CH2:24][C:11]2[N:6]3[C:7]([S:8][C:4]([CH2:3][O:2][CH3:1])=[N:5]3)=[N:9][C:10]=2[C:12]([F:15])([F:13])[F:14])[C:21](=[O:26])[CH2:20]1 |f:5.6.7|

Inputs

Step One
Name
Quantity
2 g
Type
reactant
Smiles
N1C(CCC1)=O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
N1C(CCC1)=O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
S1C=2N(N=C1)C=CN2
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
COCC1=NN2C(S1)=NC(=C2)C(F)(F)F
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC(CC1CC(N(C1)CCl)=O)(F)F
Name
Quantity
200 mL
Type
solvent
Smiles
O1CCOCC1
Name
Quantity
5 mL
Type
solvent
Smiles
O1CCOCC1
Name
Quantity
0.23 g
Type
catalyst
Smiles
[Cl-].[Cl-].[Zn+2]
Step Five
Name
Quantity
250 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
85 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
further heating of the reaction mixture
TEMPERATURE
Type
TEMPERATURE
Details
at reflux for 3 days
Duration
3 d
TEMPERATURE
Type
TEMPERATURE
Details
After cooling
EXTRACTION
Type
EXTRACTION
Details
the crude mixture is extracted by CH2Cl2 (2×250 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The cumulated organic layers are dried over MgSO4
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
condensed under reduced pressure
CUSTOM
Type
CUSTOM
Details
The residue is purified over silicagel (eluent: CH2Cl2/MeOH/NH4OH 99/1/0.1)

Outcomes

Product
Details
Reaction Time
1 d
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 74%

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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