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Dasatinib monohydrate
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Name

Dasatinib monohydrate

 EINECS 638-874-6
CAS No. 863127-77-9 Density 1.408 g/cm3
PSA 143.98000 LogP 3.39810
Solubility N/A Melting Point 97-99°C(lit.)
Formula C22H26Cl N7O2S. H2O Boiling Point N/A
Molecular Weight 506.028 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes R34; R36/37/38
Molecular Structure Molecular Structure of 863127-77-9 (Dasatinib monohydrate) Hazard Symbols C,Xi
Synonyms

5-Thiazolecarboxamide,N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-,monohydrate (9CI);BMS 35482503;Dasatinib hydrate;Dasatinib;5-Thiazolecarboxamide,N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-,hydrate (1:1);

Article Data 6

Dasatinib monohydrate Synthetic route

302962-49-8

dasatanib

863127-77-9

dasatinib monohydrate

Conditions
ConditionsYield
With ethanol; water at 80℃; for 2h; Large scale;96.44%
With water In ethanol at 75 - 80℃;
With water In ethanol at 0 - 80℃; for 5h;
With water In methanol Solvent; Heating;21 g
910297-51-7

N-(2-chloro-6-methylphenyl)-2-((2-methyl-6-(piperazin-1-yl)pyrimidin 4-yl)amino)thiazole-5-carboxamide

540-51-2

2-bromoethanol

863127-77-9

dasatinib monohydrate

Conditions
ConditionsYield
With caesium carbonate; potassium iodide In acetonitrile for 6h; Temperature; Solvent; Reagent/catalyst; Reflux;93%
103-76-4

1-(2-hydroxyethyl)piperazine

302964-08-5

2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

863127-77-9

dasatinib monohydrate

Conditions
ConditionsYield
Stage #1: 1-(2-hydroxyethyl)piperazine; 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide With N-ethyl-N,N-diisopropylamine In butan-1-ol at 118℃; for 4.5h;
Stage #2: With water In ethanol		83.2%
Stage #1: 1-(2-hydroxyethyl)piperazine; 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 2.5h;
Stage #2: With water In N,N-dimethyl-formamide at 20 - 100℃; for 2h;
302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

863127-77-9

dasatinib monohydrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium t-butanolate / tetrahydrofuran / 10 - 20 °C
1.2: 2 h / 0 - 5 °C / pH 2 - 3
2.1: N-ethyl-N,N-diisopropylamine / pentan-1-ol / 8 h / Reflux
3.1: hydrogenchloride / water / 3 h / 55 - 60 °C
4.1: potassium iodide; caesium carbonate / acetonitrile / 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium t-butanolate / tetrahydrofuran / 10 - 20 °C
1.2: 2 h / 0 - 5 °C / pH 2 - 3
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 80 - 85 °C
3.1: sulfuric acid / methanol / 5 h / 5 - 65 °C
4.1: potassium iodide; caesium carbonate / acetonitrile / 6 h / Reflux
View Scheme
302964-06-3

[5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl]-carbamic acid tert-butyl ester

863127-77-9

dasatinib monohydrate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: trifluoroacetic acid / 2 h / 25 - 30 °C
2.1: sodium t-butanolate / tetrahydrofuran / 10 - 20 °C
2.2: 2 h / 0 - 5 °C / pH 2 - 3
3.1: N-ethyl-N,N-diisopropylamine / pentan-1-ol / 8 h / Reflux
4.1: hydrogenchloride / water / 3 h / 55 - 60 °C
5.1: potassium iodide; caesium carbonate / acetonitrile / 6 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: trifluoroacetic acid / 2 h / 25 - 30 °C
2.1: sodium t-butanolate / tetrahydrofuran / 10 - 20 °C
2.2: 2 h / 0 - 5 °C / pH 2 - 3
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 80 - 85 °C
4.1: sulfuric acid / methanol / 5 h / 5 - 65 °C
5.1: potassium iodide; caesium carbonate / acetonitrile / 6 h / Reflux
View Scheme
302964-08-5

2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

863127-77-9

dasatinib monohydrate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 80 - 85 °C
2: sulfuric acid / methanol / 5 h / 5 - 65 °C
3: potassium iodide; caesium carbonate / acetonitrile / 6 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / pentan-1-ol / 8 h / Reflux
2: hydrogenchloride / water / 3 h / 55 - 60 °C
3: potassium iodide; caesium carbonate / acetonitrile / 6 h / Reflux
View Scheme
863127-77-9

dasatinib monohydrate

302962-49-8

dasatanib

Conditions
ConditionsYield
In propan-1-ol; water at 0 - 5℃; for 1h; Product distribution / selectivity; Heating / reflux;
In water; isopropyl alcohol at 0 - 5℃; for 1h; Product distribution / selectivity; Heating / reflux;

Dasatinib monohydrate Specification

1. Introduction of Dasatinib monohydrate

Dasatinib monohydrate, with the IUPAC name of N-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazole carboxamide monohydrate, is one kind of  white crystalline powder, odorless, little bitter taste. And this chemical belongs to the Product Categories of Molecular Targeted Antineoplastic. In addition, it is a drug produced by Bristol-Myers Squibb and sold under the trade name Sprycel.

2. Properties of Dasatinib monohydrate

Dasatinib monohydrate has the following properties:
Density: 1.408 g/cm3 
Index of Refraction: 1.687  

3. Use of Dasatinib monohydrate

Dasatinib (863127-77-9) is an oral dual BCR/ABL and Src family tyrosine kinases inhibitor approved for use in patients with chronic myelogenous leukemia (CML) after imatinib treatment and Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL). It is also being assessed for use in metastatic melanoma.

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