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molecular formula C16H15F6N5O B1680988 Sitagliptin CAS No. 486460-32-6

Sitagliptin

Cat. No. B1680988
M. Wt: 407.31 g/mol
InChI Key: MFFMDFFZMYYVKS-SECBINFHSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08476437B2

Procedure details

In a 50 mL three neck flask IPA (5 mL), water (2 mL) and Dibenzoyl-L-tartaric acid monohydrate (1.84 g) were taken. It was heated to 40-45° C. 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (2.0 g, % purity-94%) dissolved in IPA (5 mL) was added into reaction mixture at 60-65° C. It was stirred for 1 h at 60-65° C. It was gradually cooled to room temperature. Then it was further cooled to 0-5° C. and stirred for 1 h. The salt was filtered and washed with cold IPA. An enantiomerically enriched desired Dibenzoyl-L-tartaric acid salt of mixture of (2R) and (2S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine was obtained (Wt.-1.1 g, % Y-28.7%, Purity by HPLC-99.1%, % Chiral purity by HPLC of R-isomer 74%).
[Compound]
Name
three
Quantity
50 mL
Type
reactant
Reaction Step One
Name
Quantity
2 mL
Type
reactant
Reaction Step Two
Name
Dibenzoyl-L-tartaric acid monohydrate
Quantity
1.84 g
Type
reactant
Reaction Step Three
Name
Quantity
5 mL
Type
solvent
Reaction Step Four
Name
Quantity
5 mL
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
O.O.C([C@@](C(O)=O)(O)[C@@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.[O:29]=[C:30]([N:44]1[CH2:49][CH2:48][N:47]2[C:50]([C:53]([F:56])([F:55])[F:54])=[N:51][N:52]=[C:46]2[CH2:45]1)[CH2:31][CH:32]([NH2:43])[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42]>CC(O)C>[O:29]=[C:30]([N:44]1[CH2:49][CH2:48][N:47]2[C:50]([C:53]([F:56])([F:55])[F:54])=[N:51][N:52]=[C:46]2[CH2:45]1)[CH2:31][C@@H:32]([NH2:43])[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42] |f:1.2|

Inputs

Step One
Name
three
Quantity
50 mL
Type
reactant
Smiles
Step Two
Name
Quantity
2 mL
Type
reactant
Smiles
O
Step Three
Name
Dibenzoyl-L-tartaric acid monohydrate
Quantity
1.84 g
Type
reactant
Smiles
O.C(C1=CC=CC=C1)(=O)[C@]([C@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Step Four
Name
Quantity
2 g
Type
reactant
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Name
Quantity
5 mL
Type
solvent
Smiles
CC(C)O
Step Five
Name
Quantity
5 mL
Type
solvent
Smiles
CC(C)O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
42.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
It was stirred for 1 h at 60-65° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added into reaction mixture at 60-65° C
TEMPERATURE
Type
TEMPERATURE
Details
It was gradually cooled to room temperature
TEMPERATURE
Type
TEMPERATURE
Details
Then it was further cooled to 0-5° C.
STIRRING
Type
STIRRING
Details
stirred for 1 h
Duration
1 h
FILTRATION
Type
FILTRATION
Details
The salt was filtered
WASH
Type
WASH
Details
washed with cold IPA
ADDITION
Type
ADDITION
Details
An enantiomerically enriched desired Dibenzoyl-L-tartaric acid salt of mixture of (2R)

Outcomes

Product
Details
Reaction Time
1 h
Name
Type
product
Smiles
O=C(C[C@H](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 three neck flask IPA (5 mL), water (2 mL) and Dibenzoyl-L-tartaric acid monohydrate (1.84 g) were taken. It was heated to 40-45° C. 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (2.0 g, % purity-94%) dissolved in IPA (5 mL) was added into reaction mixture at 60-65° C. It was stirred for 1 h at 60-65° C. It was gradually cooled to room temperature. Then it was further cooled to 0-5° C. and stirred for 1 h. The salt was filtered and washed with cold IPA. An enantiomerically enriched desired Dibenzoyl-L-tartaric acid salt of mixture of (2R) and (2S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine was obtained (Wt.-1.1 g, % Y-28.7%, Purity by HPLC-99.1%, % Chiral purity by HPLC of R-isomer 74%).
[Compound]
Name
three
Quantity
50 mL
Type
reactant
Reaction Step One
Name
Quantity
2 mL
Type
reactant
Reaction Step Two
Name
Dibenzoyl-L-tartaric acid monohydrate
Quantity
1.84 g
Type
reactant
Reaction Step Three
Name
Quantity
5 mL
Type
solvent
Reaction Step Four
Name
Quantity
5 mL
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
O.O.C([C@@](C(O)=O)(O)[C@@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.[O:29]=[C:30]([N:44]1[CH2:49][CH2:48][N:47]2[C:50]([C:53]([F:56])([F:55])[F:54])=[N:51][N:52]=[C:46]2[CH2:45]1)[CH2:31][CH:32]([NH2:43])[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42]>CC(O)C>[O:29]=[C:30]([N:44]1[CH2:49][CH2:48][N:47]2[C:50]([C:53]([F:56])([F:55])[F:54])=[N:51][N:52]=[C:46]2[CH2:45]1)[CH2:31][C@@H:32]([NH2:43])[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42] |f:1.2|

Inputs

Step One
Name
three
Quantity
50 mL
Type
reactant
Smiles
Step Two
Name
Quantity
2 mL
Type
reactant
Smiles
O
Step Three
Name
Dibenzoyl-L-tartaric acid monohydrate
Quantity
1.84 g
Type
reactant
Smiles
O.C(C1=CC=CC=C1)(=O)[C@]([C@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Step Four
Name
Quantity
2 g
Type
reactant
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Name
Quantity
5 mL
Type
solvent
Smiles
CC(C)O
Step Five
Name
Quantity
5 mL
Type
solvent
Smiles
CC(C)O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
42.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
It was stirred for 1 h at 60-65° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added into reaction mixture at 60-65° C
TEMPERATURE
Type
TEMPERATURE
Details
It was gradually cooled to room temperature
TEMPERATURE
Type
TEMPERATURE
Details
Then it was further cooled to 0-5° C.
STIRRING
Type
STIRRING
Details
stirred for 1 h
Duration
1 h
FILTRATION
Type
FILTRATION
Details
The salt was filtered
WASH
Type
WASH
Details
washed with cold IPA
ADDITION
Type
ADDITION
Details
An enantiomerically enriched desired Dibenzoyl-L-tartaric acid salt of mixture of (2R)

Outcomes

Product
Details
Reaction Time
1 h
Name
Type
product
Smiles
O=C(C[C@H](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 three neck flask IPA (5 mL), water (2 mL) and Dibenzoyl-L-tartaric acid monohydrate (1.84 g) were taken. It was heated to 40-45° C. 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (2.0 g, % purity-94%) dissolved in IPA (5 mL) was added into reaction mixture at 60-65° C. It was stirred for 1 h at 60-65° C. It was gradually cooled to room temperature. Then it was further cooled to 0-5° C. and stirred for 1 h. The salt was filtered and washed with cold IPA. An enantiomerically enriched desired Dibenzoyl-L-tartaric acid salt of mixture of (2R) and (2S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine was obtained (Wt.-1.1 g, % Y-28.7%, Purity by HPLC-99.1%, % Chiral purity by HPLC of R-isomer 74%).
[Compound]
Name
three
Quantity
50 mL
Type
reactant
Reaction Step One
Name
Quantity
2 mL
Type
reactant
Reaction Step Two
Name
Dibenzoyl-L-tartaric acid monohydrate
Quantity
1.84 g
Type
reactant
Reaction Step Three
Name
Quantity
5 mL
Type
solvent
Reaction Step Four
Name
Quantity
5 mL
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
O.O.C([C@@](C(O)=O)(O)[C@@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.[O:29]=[C:30]([N:44]1[CH2:49][CH2:48][N:47]2[C:50]([C:53]([F:56])([F:55])[F:54])=[N:51][N:52]=[C:46]2[CH2:45]1)[CH2:31][CH:32]([NH2:43])[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42]>CC(O)C>[O:29]=[C:30]([N:44]1[CH2:49][CH2:48][N:47]2[C:50]([C:53]([F:56])([F:55])[F:54])=[N:51][N:52]=[C:46]2[CH2:45]1)[CH2:31][C@@H:32]([NH2:43])[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42] |f:1.2|

Inputs

Step One
Name
three
Quantity
50 mL
Type
reactant
Smiles
Step Two
Name
Quantity
2 mL
Type
reactant
Smiles
O
Step Three
Name
Dibenzoyl-L-tartaric acid monohydrate
Quantity
1.84 g
Type
reactant
Smiles
O.C(C1=CC=CC=C1)(=O)[C@]([C@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O
Step Four
Name
Quantity
2 g
Type
reactant
Smiles
O=C(CC(CC1=C(C=C(C(=C1)F)F)F)N)N1CC=2N(CC1)C(=NN2)C(F)(F)F
Name
Quantity
5 mL
Type
solvent
Smiles
CC(C)O
Step Five
Name
Quantity
5 mL
Type
solvent
Smiles
CC(C)O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
42.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
It was stirred for 1 h at 60-65° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added into reaction mixture at 60-65° C
TEMPERATURE
Type
TEMPERATURE
Details
It was gradually cooled to room temperature
TEMPERATURE
Type
TEMPERATURE
Details
Then it was further cooled to 0-5° C.
STIRRING
Type
STIRRING
Details
stirred for 1 h
Duration
1 h
FILTRATION
Type
FILTRATION
Details
The salt was filtered
WASH
Type
WASH
Details
washed with cold IPA
ADDITION
Type
ADDITION
Details
An enantiomerically enriched desired Dibenzoyl-L-tartaric acid salt of mixture of (2R)

Outcomes

Product
Details
Reaction Time
1 h
Name
Type
product
Smiles
O=C(C[C@H](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.
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