![molecular formula C16H13F6N5O B8811113 3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one](/img/structure/B8811113.png)
3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one
Numéro de catalogue B8811113
Poids moléculaire: 405.30 g/mol
Clé InChI: RLSFDUAUKXKPCZ-UHFFFAOYSA-N
Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.
Patent
US08476437B2
Procedure details
In a 50 mL round bottom flask dry THF (17 mL) was taken. It was cooled to −10° C. and 2.0 M Borane methyl sulfide complex solutions in THF (7.41 mL) were added. After that methanesulfonic acid (2.4 mL) was added dropwise at −10° C. over a period of 15-30 min. 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine (2.0 g) is mixed in a solvent mixture of THF (5.0 mL) and IPA (5.0 mL) and added into the reaction mixture, keeping the temperature between −10 to −5. It was stirred for 4 h at −10 to −5° C. Reaction mixture was poured into cold water. It was basified by adding aq. ammonia solution. Product was extracted in ethyl acetate. The organic layer was collected, was washed with water and dried over anhydrous sodium sulfate. Solvent was evaporated at reduced pressure to obtain the product. (Wt.-2.0 g, % Y-100%, % H2O-5.18%, % Purity by HPLC-96.6%). XRD-amorphous-FIG. 1
Quantity
2 g
Type
reactant
Reaction Step Two
Identifiers
|
REACTION_CXSMILES
|
CS(O)(=O)=O.[O:6]=[C:7]([N:21]1[CH2:26][CH2:25][N:24]2[C:27]([C:30]([F:33])([F:32])[F:31])=[N:28][N:29]=[C:23]2[CH2:22]1)[CH:8]=[C:9]([NH2:20])[CH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19].CC(O)C.N>C1COCC1.O>[O:6]=[C:7]([N:21]1[CH2:26][CH2:25][N:24]2[C:27]([C:30]([F:33])([F:32])[F:31])=[N:28][N:29]=[C:23]2[CH2:22]1)[CH2:8][CH:9]([NH2:20])[CH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19]
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
2.4 mL
|
|
Type
|
reactant
|
|
Smiles
|
CS(=O)(=O)O
|
Step Two
|
Name
|
|
|
Quantity
|
2 g
|
|
Type
|
reactant
|
|
Smiles
|
O=C(C=C(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
|
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
reactant
|
|
Smiles
|
CC(C)O
|
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
N
|
Step Four
|
Name
|
|
|
Quantity
|
7.41 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Five
|
Name
|
|
|
Quantity
|
17 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Six
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Seven
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
-10 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
It was stirred for 4 h at −10 to −5° C
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
added into the reaction mixture
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Reaction mixture
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
Product was extracted in ethyl acetate
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The organic layer was collected
|
WASH
|
Type
|
WASH
|
|
Details
|
was washed with water
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
dried over anhydrous sodium sulfate
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Solvent was evaporated at reduced pressure
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to obtain the product
|
Outcomes
Product
Details
Reaction Time |
4 h |
|
Name
|
|
|
Type
|
|
|
Smiles
|
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
|
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
US08476437B2
Procedure details
In a 50 mL round bottom flask dry THF (17 mL) was taken. It was cooled to −10° C. and 2.0 M Borane methyl sulfide complex solutions in THF (7.41 mL) were added. After that methanesulfonic acid (2.4 mL) was added dropwise at −10° C. over a period of 15-30 min. 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine (2.0 g) is mixed in a solvent mixture of THF (5.0 mL) and IPA (5.0 mL) and added into the reaction mixture, keeping the temperature between −10 to −5. It was stirred for 4 h at −10 to −5° C. Reaction mixture was poured into cold water. It was basified by adding aq. ammonia solution. Product was extracted in ethyl acetate. The organic layer was collected, was washed with water and dried over anhydrous sodium sulfate. Solvent was evaporated at reduced pressure to obtain the product. (Wt.-2.0 g, % Y-100%, % H2O-5.18%, % Purity by HPLC-96.6%). XRD-amorphous-FIG. 1
Quantity
2 g
Type
reactant
Reaction Step Two
Identifiers
|
REACTION_CXSMILES
|
CS(O)(=O)=O.[O:6]=[C:7]([N:21]1[CH2:26][CH2:25][N:24]2[C:27]([C:30]([F:33])([F:32])[F:31])=[N:28][N:29]=[C:23]2[CH2:22]1)[CH:8]=[C:9]([NH2:20])[CH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19].CC(O)C.N>C1COCC1.O>[O:6]=[C:7]([N:21]1[CH2:26][CH2:25][N:24]2[C:27]([C:30]([F:33])([F:32])[F:31])=[N:28][N:29]=[C:23]2[CH2:22]1)[CH2:8][CH:9]([NH2:20])[CH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19]
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
2.4 mL
|
|
Type
|
reactant
|
|
Smiles
|
CS(=O)(=O)O
|
Step Two
|
Name
|
|
|
Quantity
|
2 g
|
|
Type
|
reactant
|
|
Smiles
|
O=C(C=C(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
|
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
reactant
|
|
Smiles
|
CC(C)O
|
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
N
|
Step Four
|
Name
|
|
|
Quantity
|
7.41 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Five
|
Name
|
|
|
Quantity
|
17 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Six
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Seven
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
-10 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
It was stirred for 4 h at −10 to −5° C
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
added into the reaction mixture
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Reaction mixture
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
Product was extracted in ethyl acetate
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The organic layer was collected
|
WASH
|
Type
|
WASH
|
|
Details
|
was washed with water
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
dried over anhydrous sodium sulfate
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Solvent was evaporated at reduced pressure
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to obtain the product
|
Outcomes
Product
Details
Reaction Time |
4 h |
|
Name
|
|
|
Type
|
|
|
Smiles
|
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
|
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
US08476437B2
Procedure details
In a 50 mL round bottom flask dry THF (17 mL) was taken. It was cooled to −10° C. and 2.0 M Borane methyl sulfide complex solutions in THF (7.41 mL) were added. After that methanesulfonic acid (2.4 mL) was added dropwise at −10° C. over a period of 15-30 min. 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine (2.0 g) is mixed in a solvent mixture of THF (5.0 mL) and IPA (5.0 mL) and added into the reaction mixture, keeping the temperature between −10 to −5. It was stirred for 4 h at −10 to −5° C. Reaction mixture was poured into cold water. It was basified by adding aq. ammonia solution. Product was extracted in ethyl acetate. The organic layer was collected, was washed with water and dried over anhydrous sodium sulfate. Solvent was evaporated at reduced pressure to obtain the product. (Wt.-2.0 g, % Y-100%, % H2O-5.18%, % Purity by HPLC-96.6%). XRD-amorphous-FIG. 1
Quantity
2 g
Type
reactant
Reaction Step Two
Identifiers
|
REACTION_CXSMILES
|
CS(O)(=O)=O.[O:6]=[C:7]([N:21]1[CH2:26][CH2:25][N:24]2[C:27]([C:30]([F:33])([F:32])[F:31])=[N:28][N:29]=[C:23]2[CH2:22]1)[CH:8]=[C:9]([NH2:20])[CH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19].CC(O)C.N>C1COCC1.O>[O:6]=[C:7]([N:21]1[CH2:26][CH2:25][N:24]2[C:27]([C:30]([F:33])([F:32])[F:31])=[N:28][N:29]=[C:23]2[CH2:22]1)[CH2:8][CH:9]([NH2:20])[CH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19]
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
2.4 mL
|
|
Type
|
reactant
|
|
Smiles
|
CS(=O)(=O)O
|
Step Two
|
Name
|
|
|
Quantity
|
2 g
|
|
Type
|
reactant
|
|
Smiles
|
O=C(C=C(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
|
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
reactant
|
|
Smiles
|
CC(C)O
|
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
N
|
Step Four
|
Name
|
|
|
Quantity
|
7.41 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Five
|
Name
|
|
|
Quantity
|
17 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1CCOC1
|
Step Six
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Seven
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
-10 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
It was stirred for 4 h at −10 to −5° C
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
added into the reaction mixture
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Reaction mixture
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
Product was extracted in ethyl acetate
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The organic layer was collected
|
WASH
|
Type
|
WASH
|
|
Details
|
was washed with water
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
dried over anhydrous sodium sulfate
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Solvent was evaporated at reduced pressure
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to obtain the product
|
Outcomes
Product
Details
Reaction Time |
4 h |
|
Name
|
|
|
Type
|
|
|
Smiles
|
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
|
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. |
