• Name

  Dasatinib monohydrate

• EINECS 638-874-6
• CAS No. 863127-77-9
• Article Data6
• CAS DataBase
• Density 1.408 g/cm3
• Solubility
• Melting Point 97-99°C(lit.)
• Formula C₂₂H₂₆Cl N₇O₂S^. H₂O
• Boiling Point
• Molecular Weight 506.028
• Flash Point
• Transport Information
• Appearance
• Safety
• Risk Codes R34; R36/37/38
• Molecular Structure
• 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);
• PSA 143.98000
• LogP 3.39810

Synthetic route

302962-49-8

dasatanib

863127-77-9

dasatinib monohydrate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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