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molecular formula C22H26ClN7O2S B023192 Dasatinib-d8 CAS No. 1132093-70-9

Dasatinib-d8

Cat. No. B023192
M. Wt: 496.1 g/mol
InChI Key: ZBNZXTGUTAYRHI-COMRDEPKSA-N
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Patent
US08067423B2

Procedure details

Dasatinib (form A3, 3.50 g) was dissolved in a mixture of i-PrOH—H2O 30:8 (in 140 ml) under reflux. The solution was slowly cooled to about 70° C. The product started to crystallized at 65-70° C. Temperature was kept at this value for about 20 min then it was decreased to 50° C. and kept for 15 min. The mixture was slowly cooled to room temperature and stirred at room temperature for 1 h. The product was filtered off, washed with i-PrOH (2×) and dried under reduced pressure at 50° C. for 3 h. Yield: 2.44 g.
Name
Dasatinib
Quantity
3.5 g
Type
reactant
Reaction Step One
Quantity
140 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[CH3:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[S:15][C:14]([NH:16][C:17]3[CH:18]=[C:19]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]4)[N:20]=[C:21]([CH3:23])[N:22]=3)=[N:13][CH:12]=2)=[O:10])=[C:6]([Cl:33])[CH:5]=[CH:4][CH:3]=1.C([O-])(C)C>C(O)(C)C.O>[CH3:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[S:15][C:14]([NH:16][C:17]3[CH:18]=[C:19]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]4)[N:20]=[C:21]([CH3:23])[N:22]=3)=[N:13][CH:12]=2)=[O:10])=[C:6]([Cl:33])[CH:5]=[CH:4][CH:3]=1 |f:0.1,2.3|

Inputs

Step One
Name
Dasatinib
Quantity
3.5 g
Type
reactant
Smiles
CC1=CC=CC(=C1NC(=O)C2=CN=C(S2)NC=3C=C(N=C(N3)C)N4CCN(CC4)CCO)Cl.C(C)(C)[O-]
Name
Quantity
140 mL
Type
solvent
Smiles
C(C)(C)O.O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
70 °C
Stirring
Type
CUSTOM
Details
stirred at room temperature for 1 h
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
under reflux
CUSTOM
Type
CUSTOM
Details
to crystallized at 65-70° C
CUSTOM
Type
CUSTOM
Details
was decreased to 50° C.
WAIT
Type
WAIT
Details
kept for 15 min
Duration
15 min
TEMPERATURE
Type
TEMPERATURE
Details
The mixture was slowly cooled to room temperature
FILTRATION
Type
FILTRATION
Details
The product was filtered off
WASH
Type
WASH
Details
washed with i-PrOH (2×)
CUSTOM
Type
CUSTOM
Details
dried under reduced pressure at 50° C. for 3 h
Duration
3 h

Outcomes

Product
Details
Reaction Time
20 min
Name
Type
Smiles
CC1=CC=CC(=C1NC(=O)C2=CN=C(S2)NC=3C=C(N=C(N3)C)N4CCN(CC4)CCO)Cl

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
US08067423B2

Procedure details

Dasatinib (form A3, 3.50 g) was dissolved in a mixture of i-PrOH—H2O 30:8 (in 140 ml) under reflux. The solution was slowly cooled to about 70° C. The product started to crystallized at 65-70° C. Temperature was kept at this value for about 20 min then it was decreased to 50° C. and kept for 15 min. The mixture was slowly cooled to room temperature and stirred at room temperature for 1 h. The product was filtered off, washed with i-PrOH (2×) and dried under reduced pressure at 50° C. for 3 h. Yield: 2.44 g.
Name
Dasatinib
Quantity
3.5 g
Type
reactant
Reaction Step One
Quantity
140 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[CH3:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[S:15][C:14]([NH:16][C:17]3[CH:18]=[C:19]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]4)[N:20]=[C:21]([CH3:23])[N:22]=3)=[N:13][CH:12]=2)=[O:10])=[C:6]([Cl:33])[CH:5]=[CH:4][CH:3]=1.C([O-])(C)C>C(O)(C)C.O>[CH3:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[S:15][C:14]([NH:16][C:17]3[CH:18]=[C:19]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]4)[N:20]=[C:21]([CH3:23])[N:22]=3)=[N:13][CH:12]=2)=[O:10])=[C:6]([Cl:33])[CH:5]=[CH:4][CH:3]=1 |f:0.1,2.3|

Inputs

Step One
Name
Dasatinib
Quantity
3.5 g
Type
reactant
Smiles
CC1=CC=CC(=C1NC(=O)C2=CN=C(S2)NC=3C=C(N=C(N3)C)N4CCN(CC4)CCO)Cl.C(C)(C)[O-]
Name
Quantity
140 mL
Type
solvent
Smiles
C(C)(C)O.O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
70 °C
Stirring
Type
CUSTOM
Details
stirred at room temperature for 1 h
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
under reflux
CUSTOM
Type
CUSTOM
Details
to crystallized at 65-70° C
CUSTOM
Type
CUSTOM
Details
was decreased to 50° C.
WAIT
Type
WAIT
Details
kept for 15 min
Duration
15 min
TEMPERATURE
Type
TEMPERATURE
Details
The mixture was slowly cooled to room temperature
FILTRATION
Type
FILTRATION
Details
The product was filtered off
WASH
Type
WASH
Details
washed with i-PrOH (2×)
CUSTOM
Type
CUSTOM
Details
dried under reduced pressure at 50° C. for 3 h
Duration
3 h

Outcomes

Product
Details
Reaction Time
20 min
Name
Type
Smiles
CC1=CC=CC(=C1NC(=O)C2=CN=C(S2)NC=3C=C(N=C(N3)C)N4CCN(CC4)CCO)Cl

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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