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863127-77-9

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863127-77-9 Usage

Uses

Different sources of media describe the Uses of 863127-77-9 differently. You can refer to the following data:
1. antineoplastic
2. Dasatinib Monohydrate is an orally bioavailable synthetic small molecule-inhibitor of SRC-family protein-tyrosine kinases. It is a COVID19-related research product.

Definition

ChEBI: A hydrate that is the monohydrate of dasatinib. It is used for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhyd ous dasatinib (INN).

Biological Activity

chronic myeloid leukemia (cml) is a disease characterized by the presence of the philadelphia (ph+) chromosome and its oncogenic product, bcr-abl, that is present in >90% of the patients. dasatinib (bms-354825) is a novel, potent, and multitargeted kinase inhibitor that targets abl, src, kit, pdgfr, and other tyrosine kinases.

in vitro

dasatinib is a potent atp-competitive inhibitor in biochemical assays with broad-spectrum antiproliferative activities against hematological and solid tumor cell lines. dasatinib was more potent than imatinib at inhibiting nonmutated bcr-abl kinase activity. in addition, the kinase activity of 14 out of 15 different clinically relevant, imatinib-resistant bcr-abl isoforms was successfully inhibited [1].

in vivo

mice were dosed with dasatinib or vehicle alone by gavage for 2 weeks, beginning 3 days after injection of ba/f3 cells. all vehicle-treated mice developed progressive disease. in contrast, dasatinib–treated mice harboring nonmutant bcr-abl or the clinically common imatinib-resistant mutation m351t appeared healthy with no evidence of weight loss, lethargy, or ruffled fur and showed more than one log lower levels of bioluminescent activity after 2 weeks of therapy [2].

IC 50

0.55 and 3.0 nm for src and bcr-abl tyrosine kinases, respectively

references

[1] shah np, tran c, lee fy, chen p, norris d, sawyers cl. overriding imatinib resistance with a novel abl kinase inhibitor. science. 2004 jul 16;305(5682):399-401.[2] monika conchon, carla maria boquimpani de moura freitas, maria aparecida do carmo rego, and josé wilson ramos braga junior. dasatinib -

Check Digit Verification of cas no

The CAS Registry Mumber 863127-77-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,6,3,1,2 and 7 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 863127-77:
(8*8)+(7*6)+(6*3)+(5*1)+(4*2)+(3*7)+(2*7)+(1*7)=179
179 % 10 = 9
So 863127-77-9 is a valid CAS Registry Number.
InChI:InChI=1/C22H27N7O2S2.H2O/c1-14-4-3-5-16(32)20(14)27-21(31)17-13-23-22(33-17)26-18-12-19(25-15(2)24-18)29-8-6-28(7-9-29)10-11-30;/h3-5,12-13,30,32H,6-11H2,1-2H3,(H,27,31)(H,23,24,25,26);1H2

863127-77-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-1,3-thiazole-5-carboxamide,hydrate

1.2 Other means of identification

Product number -
Other names UNII-RBZ1571X5H

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:863127-77-9 SDS

863127-77-9Synthetic route

dasatanib
302962-49-8

dasatanib

dasatinib monohydrate
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
N-(2-chloro-6-methylphenyl)-2-((2-methyl-6-(piperazin-1-yl)pyrimidin 4-yl)amino)thiazole-5-carboxamide
910297-51-7

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

2-bromoethanol
540-51-2

2-bromoethanol

dasatinib monohydrate
863127-77-9

dasatinib monohydrate

Conditions
ConditionsYield
With caesium carbonate; potassium iodide In acetonitrile for 6h; Temperature; Solvent; Reagent/catalyst; Reflux;93%
1-(2-hydroxyethyl)piperazine
103-76-4

1-(2-hydroxyethyl)piperazine

2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
302964-08-5

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

dasatinib monohydrate
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;
2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide
302964-24-5

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

dasatinib monohydrate
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
[5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl]-carbamic acid tert-butyl ester
302964-06-3

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

dasatinib monohydrate
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
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
302964-08-5

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

dasatinib monohydrate
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
dasatinib monohydrate
863127-77-9

dasatinib monohydrate

dasatanib
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;

863127-77-9Downstream Products

863127-77-9Relevant articles and documents

Preparation method for dasatinib monohydrate

-

Paragraph 0041; 0072-0073, (2020/07/13)

The invention provides a preparation method for a dasatinib monohydrate. The dasatinib monohydrate is obtained by a reaction of dasatinib in an ethanol aqueous solution. According to a technical scheme of the invention, the high-quality dasatinib monohydrate can be obtained; tedious separation and purification steps are avoided; operation is simple; the waste of raw materials is also avoided; theproduction cost is reduced; and the preparation method is more applicable to industrial production.

A convenient new and efficient commercial synthetic route for dasatinib (Sprycel)

Suresh, Garbapu,Nadh, Ratnakaram Venkata,Srinivasu, Navuluri,Yennity, Durgaprasad

, p. 1610 - 1621 (2017/09/08)

A new and efficient synthetic route for dual-Src/Abl kinase inhibitor dasatinib (Sprycel), an anticancer drug, is described. This commercially viable process yields dasatinib monohydrate free of potential impurities with consistent yield of 68% in route A and 61% in route B with HPLC purity >99.80% over four stages.

ORAL ADMINISTRATION OF N-(2-CHLORO-6-METHYLPHENYL)-2-[[6-[4-(2-HYDROXYETHYL)-1-PIPERAZINYL]-2-METHYL-4-PYRIMIDINYL]AMINO]-1,3-THIAZOLE-5-CARBOXAMIDE AND SALTS THEREOF

-

Page/Page column 57-58, (2010/11/26)

Disclosed are a method of treating cancer and/or other proliferative diseases comprising orally administering N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)-1-piperazinyl)-2-methyl-4-pyrimidinyl)amino)-1,3-thiazole-5-carboxamide or a salt thereof, and pharmaceutical compositions comprising N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)-1-piperazinyl)-2-methyl-4-pyrimidinyl)amino)-1,3-thiazole-5-carboxamide or a salt thereof. Also disclosed are N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)-1-piperazinyl)-2-methyl-4-pyrimidinyl)amino)-1,3-thiazole-5-carboxamide salts, as well as crystalline forms thereof.

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