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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
Attention: For research use only. Not for human or veterinary use.
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Patent
US08067423B2

Procedure details

Dasatinib butanolate (form BU-2, 1.00 g, 2.05 mmol) was heated in a mixture of ethanol (22 ml) and water (3 ml) at 75-80° C. to achieve complete dissolution. Water was added (8 ml) at the same temperature. The solution was cooled to 70° C. and maintained at 70° C. for 1 h. Temperature was lowered from 70° C. to 5° C. during 2 h, and maintained between 0-5° C. for 2 h. The product was filtered and washed with EtOH/H2O (1:1, 2×10 ml) and dried under reduced pressure at 40° C./8 h. Yield: 0.61 g.
Name
Dasatinib butanolate
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
22 mL
Type
solvent
Reaction Step One
Name
Quantity
3 mL
Type
solvent
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

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-])CCC>C(O)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|

Inputs

Step One
Name
Dasatinib butanolate
Quantity
1 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(CCC)[O-]
Name
Quantity
22 mL
Type
solvent
Smiles
C(C)O
Name
Quantity
3 mL
Type
solvent
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
70 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

DISSOLUTION
Type
DISSOLUTION
Details
dissolution
TEMPERATURE
Type
TEMPERATURE
Details
maintained at 70° C. for 1 h
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
maintained between 0-5° C. for 2 h
Duration
2 h
FILTRATION
Type
FILTRATION
Details
The product was filtered
WASH
Type
WASH
Details
washed with EtOH/H2O (1:1, 2×10 ml)
CUSTOM
Type
CUSTOM
Details
dried under reduced pressure at 40° C./8 h
Duration
8 h

Outcomes

Product
Details
Reaction Time
2 h
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 butanolate (form BU-2, 1.00 g, 2.05 mmol) was heated in a mixture of ethanol (22 ml) and water (3 ml) at 75-80° C. to achieve complete dissolution. Water was added (8 ml) at the same temperature. The solution was cooled to 70° C. and maintained at 70° C. for 1 h. Temperature was lowered from 70° C. to 5° C. during 2 h, and maintained between 0-5° C. for 2 h. The product was filtered and washed with EtOH/H2O (1:1, 2×10 ml) and dried under reduced pressure at 40° C./8 h. Yield: 0.61 g.
Name
Dasatinib butanolate
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
22 mL
Type
solvent
Reaction Step One
Name
Quantity
3 mL
Type
solvent
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

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-])CCC>C(O)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|

Inputs

Step One
Name
Dasatinib butanolate
Quantity
1 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(CCC)[O-]
Name
Quantity
22 mL
Type
solvent
Smiles
C(C)O
Name
Quantity
3 mL
Type
solvent
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
70 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

DISSOLUTION
Type
DISSOLUTION
Details
dissolution
TEMPERATURE
Type
TEMPERATURE
Details
maintained at 70° C. for 1 h
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
maintained between 0-5° C. for 2 h
Duration
2 h
FILTRATION
Type
FILTRATION
Details
The product was filtered
WASH
Type
WASH
Details
washed with EtOH/H2O (1:1, 2×10 ml)
CUSTOM
Type
CUSTOM
Details
dried under reduced pressure at 40° C./8 h
Duration
8 h

Outcomes

Product
Details
Reaction Time
2 h
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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