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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
US09108954B2

Procedure details

1-(2-hydroxyethyl)piperazine (Compound 3) (65 g, 0.5 mol), 2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide (Compound 14) (43.9 g, 0.1 mol), n-butanol (670 mL) and DIPEA (28.3 g, 0.2 mol) were mixed in reaction flask and reacted by refluxing for 7 h. After the reactant was cooled down to room temperature, crystals precipitated overnight. After air pump filtration, the cake was rinsed with n-butanol (500 mL) by stirring for 30 min. Then filtrated and the cake was dried to give white solid target Compound 1 (42.9 g, yield: 87.9%).
Quantity
65 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide
Quantity
43.9 g
Type
reactant
Reaction Step One
Name
Compound 14
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
28.3 g
Type
reactant
Reaction Step One
Quantity
670 mL
Type
solvent
Reaction Step One
Yield
87.9%

Identifiers

REACTION_CXSMILES
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[C:11]1[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:18][C:19]2[S:20][C:21]([C:24]([NH:26][C:27]3[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:34])=[O:25])=[CH:22][N:23]=2)[CH:12]=1.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:33][C:32]1[C:27]([NH:26][C:24]([C:21]2[S:20][C:19]([NH:18][C:13]3[CH:12]=[C:11]([N:7]4[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]4)[N:16]=[C:15]([CH3:17])[N:14]=3)=[N:23][CH:22]=2)=[O:25])=[C:28]([Cl:34])[CH:29]=[CH:30][CH:31]=1

Inputs

Step One
Name
Quantity
65 g
Type
reactant
Smiles
OCCN1CCNCC1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
OCCN1CCNCC1
Name
2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide
Quantity
43.9 g
Type
reactant
Smiles
BrC1=CC(=NC(=N1)C)NC=1SC(=CN1)C(=O)NC1=C(C=CC=C1C)Cl
Name
Compound 14
Quantity
0 (± 1) mol
Type
reactant
Smiles
BrC1=CC(=NC(=N1)C)NC=1SC(=CN1)C(=O)NC1=C(C=CC=C1C)Cl
Name
Quantity
28.3 g
Type
reactant
Smiles
CCN(C(C)C)C(C)C
Name
Quantity
670 mL
Type
solvent
Smiles
C(CCC)O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
by stirring for 30 min
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
reacted
TEMPERATURE
Type
TEMPERATURE
Details
by refluxing for 7 h
Duration
7 h
CUSTOM
Type
CUSTOM
Details
crystals precipitated overnight
Duration
8 (± 8) h
FILTRATION
Type
FILTRATION
Details
After air pump filtration
WASH
Type
WASH
Details
the cake was rinsed with n-butanol (500 mL)
FILTRATION
Type
FILTRATION
Details
Then filtrated
CUSTOM
Type
CUSTOM
Details
the cake was dried

Outcomes

Product
Details
Reaction Time
30 min
Name
Type
product
Smiles
CC1=CC=CC(=C1NC(=O)C2=CN=C(S2)NC=3C=C(N=C(N3)C)N4CCN(CC4)CCO)Cl
Measurements
Type Value Analysis
AMOUNT: MASS 42.9 g
YIELD: PERCENTYIELD 87.9%
YIELD: CALCULATEDPERCENTYIELD 87.9%

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
US09108954B2

Procedure details

1-(2-hydroxyethyl)piperazine (Compound 3) (65 g, 0.5 mol), 2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide (Compound 14) (43.9 g, 0.1 mol), n-butanol (670 mL) and DIPEA (28.3 g, 0.2 mol) were mixed in reaction flask and reacted by refluxing for 7 h. After the reactant was cooled down to room temperature, crystals precipitated overnight. After air pump filtration, the cake was rinsed with n-butanol (500 mL) by stirring for 30 min. Then filtrated and the cake was dried to give white solid target Compound 1 (42.9 g, yield: 87.9%).
Quantity
65 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide
Quantity
43.9 g
Type
reactant
Reaction Step One
Name
Compound 14
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
28.3 g
Type
reactant
Reaction Step One
Quantity
670 mL
Type
solvent
Reaction Step One
Yield
87.9%

Identifiers

REACTION_CXSMILES
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[C:11]1[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:18][C:19]2[S:20][C:21]([C:24]([NH:26][C:27]3[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:34])=[O:25])=[CH:22][N:23]=2)[CH:12]=1.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:33][C:32]1[C:27]([NH:26][C:24]([C:21]2[S:20][C:19]([NH:18][C:13]3[CH:12]=[C:11]([N:7]4[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]4)[N:16]=[C:15]([CH3:17])[N:14]=3)=[N:23][CH:22]=2)=[O:25])=[C:28]([Cl:34])[CH:29]=[CH:30][CH:31]=1

Inputs

Step One
Name
Quantity
65 g
Type
reactant
Smiles
OCCN1CCNCC1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
OCCN1CCNCC1
Name
2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide
Quantity
43.9 g
Type
reactant
Smiles
BrC1=CC(=NC(=N1)C)NC=1SC(=CN1)C(=O)NC1=C(C=CC=C1C)Cl
Name
Compound 14
Quantity
0 (± 1) mol
Type
reactant
Smiles
BrC1=CC(=NC(=N1)C)NC=1SC(=CN1)C(=O)NC1=C(C=CC=C1C)Cl
Name
Quantity
28.3 g
Type
reactant
Smiles
CCN(C(C)C)C(C)C
Name
Quantity
670 mL
Type
solvent
Smiles
C(CCC)O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
by stirring for 30 min
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
reacted
TEMPERATURE
Type
TEMPERATURE
Details
by refluxing for 7 h
Duration
7 h
CUSTOM
Type
CUSTOM
Details
crystals precipitated overnight
Duration
8 (± 8) h
FILTRATION
Type
FILTRATION
Details
After air pump filtration
WASH
Type
WASH
Details
the cake was rinsed with n-butanol (500 mL)
FILTRATION
Type
FILTRATION
Details
Then filtrated
CUSTOM
Type
CUSTOM
Details
the cake was dried

Outcomes

Product
Details
Reaction Time
30 min
Name
Type
product
Smiles
CC1=CC=CC(=C1NC(=O)C2=CN=C(S2)NC=3C=C(N=C(N3)C)N4CCN(CC4)CCO)Cl
Measurements
Type Value Analysis
AMOUNT: MASS 42.9 g
YIELD: PERCENTYIELD 87.9%
YIELD: CALCULATEDPERCENTYIELD 87.9%

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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