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Dasatinib 99% Manufactuered in China best quality
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302962-49-8 Usage

Uses

Directly targets wild-type and mutant c-Abl kinase domains

Chemical Synthesis

A concise and efficient route was developed for the synthesis of dasatinib. Reaction of 2-chlorothioa-zole (18) with n-butyllithium at low temperature followed by addition of 2-chloro-6-methylphenyl isocyanate (19) gave anilide 20 in 86% yield. The amide 20 was protected as corresponding 4-methoxy benzyl (PMB) anilide 22 in 95% yield which was subsequently reacted with 4- amino-6-chloro-2-methylpyrimidine (23) in the presence of sodium hydride in hot THF to give compound 24 in 83% yield. The PMB protecting group was then removed with triflic acid to give compound 25 in 99% yield. Compound 25 was reacted with 1-(2-hydroxyethyl)piperazine (26) in refluxing dioxane to give dasatinib (III) in 91% yield.

Description

Dasatinib, developed and marketed by Bristol Myers, is the first approved oral tyrosine kinase inhibitor which binds to multiple conformations of ABL kinase for the treatment of two leukemia indications: chronic myeloid leukemia (CML) and Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL). Dasatinib is a highly potent, ATPcompetitive ATPcompetitive kinase inhibitor which, at nanomolar concentrations, inhibits BCR-ABL, SRC family, c-KIT, EPHA2 and PDGFR-B.

Uses

Suitable for treatment of chronic myeloid leukemia which is resistant or intolerant to the treating programs including imatinib mesylate.

Uses

A new, oral, small-molecule Tyrosine Kinase Inhibitor (TKI) for the treatment of CML. Antineoplastic

Chemical Properties

Pale-Yellow Solid

Leukemia drug

Dasatinib is an oral potent oncogenic kinase inhibitor, which can block signal of cancer cell replication acceleration , in May 2009, the US Food and Drug Administration (FDA) formally approved the sale of dasatinib , It has been clinically used for the treatment of various chronic myeloid leukemia (CML), including treatment of chronic myeloid leukemia which is resistant or intolerant to the treating programs including imatinib mesylate., Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph + ALL) and the treatment of patients with solid tumors. October 28, 2010 ,the FDA approved dasatinib (Sprycel) of the new indication which is used for the treatment of the rare leukemia first diagnosed Philadelphia chromosome-positive called chronic myeloid leukemia (Ph + CP-CML) . The disease is a blood and bone marrow disease associated with genetic abnormality . An open-label randomized clinical trial conducted in patients with CP-CML evaluated the safety and efficacy of dasatinib . Common side effects include decreased activity of the bone marrow caused by red blood cells, white blood cells and platelets decreased (myelosuppression), fluid retention, diarrhea, headache, musculoskeletal pain, and rash. October 11, 2011, the US Food and Drug Administration (FDA) said the leukemia drug dasatinib (Sprycel, Bristol-Myers Squibb Company) might increase pulmonary arterial hypertension (PAH) risk. Pulmonary hypertension is a rare but serious disease that can lead to the condition that heart pumping blood to the lungs becomes more difficult by raising the pressure . PAH symptoms include shortness of breath, fatigue, swelling of the legs and ankles, clinicians must differentiate these symptoms from other similar symptoms. Since 2006 Dasatinib was approved in the US market ,there had been 12 associated pulmonary hypertension events ,pulmonary hypertension symptoms included shortness of breath, fatigue, hypoxia and fluid retention, patients then were confirmed pulmonary hypertension by the results of right heart catheterization ,studies have shown that the biggest cause of the disease may come from patients taking dasatinib. The above information is edited by the Chemicalbook of Tian Ye.

Uses

Dasatinib is a novel, potent and multi-targeted inhibitor that targets Abl, Src and c-Kit, with IC50 of <1 nM, 0.8 nM and 79 nM, respectively.

General Description

Dasatinib is available in 20-, 50-, and 70-mg tablets fororal administration in the treatment of CML and ALL thatare Ph1 positive. Although dasatinib is more potent thanimatinib, bioavailability is much lower with values rangingbetween 14% to 34%. The agent is extensively metabolizedwith as many as 29 metabolites seen as result of oxidationby primarily CYP3A4 and phase II conjugation.The agent may act as an inhibitor of CYP3A4 andCYP2C8. Metabolism does give an active metabolite, but this accounts for only 5% of the total and is not believed tobe important for the overall activity of the agent. Dasatinibis 95% protein bound with a terminal half-life of 3 to5 hours. The majority of the drug and metabolites are eliminatedin the feces. The most common side effects are skinrash, nausea, diarrhea, and fatigue. Serious side effects includemyelosuppression appearing as neutropenia andthrombocytopenia, bleeding of the brain and GI tract, andfluid retention.

Chemical properties

White solid

Brand name

Sprycel (Bristol-Myers Squibb).

Originator

Bristol–Myers Squibb (US)
InChI:InChI=1/C22H26ClN7O2S.H2O/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31;/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27);1H2

302962-49-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Dasatinib

1.2 Other means of identification

Product number -
Other names Dasatinib Tablets

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:302962-49-8 SDS

302962-49-8Synthetic route

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

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
With tetrabutylammomium bromide In acetonitrile at 30 - 80℃;97%
In propan-1-ol at 115 - 120℃; Temperature;93%
With copper(l) chloride In N,N-dimethyl-formamide at 65℃; for 2h; Temperature; Reagent/catalyst;91.6%
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide
1245157-85-0

N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
With potassium carbonate In methanol; water at 60 - 65℃; for 3h; Solvent; Reagent/catalyst;96.4%
Stage #1: N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide With water; sodium hydroxide at 50℃; for 2h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=4;
88.7%
Stage #1: N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide With water; sodium hydroxide at 50℃; for 2h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=4;
88.7%
C20H24ClN5O4S

C20H24ClN5O4S

acetamidine hydrochloride
124-42-5

acetamidine hydrochloride

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
With sodium methylate In methanol at 65℃; for 4h; Temperature; Cooling with ice;95.3%
1-(2-hydroxyethyl)piperazine
103-76-4

1-(2-hydroxyethyl)piperazine

2,4-dichloro-2-methylpyrimidine
1780-26-3

2,4-dichloro-2-methylpyrimidine

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

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: 1-(2-hydroxyethyl)piperazine; 2,4-dichloro-2-methylpyrimidine With potassium phosphate; 1-butyl-3-methylimidazolium aminoethanic acid salt at 80℃; for 1.5h;
Stage #2: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide at 20 - 80℃; for 2h; Reagent/catalyst;
92.27%
Stage #1: 1-(2-hydroxyethyl)piperazine; 2,4-dichloro-2-methylpyrimidine With potassium phosphate; 1-butyl-3-methylimidazolium aminoethanic acid salt In N,N-dimethyl acetamide at 80℃; for 2h;
Stage #2: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide In N,N-dimethyl acetamide at 80℃; for 3h; Solvent;
89.31%
Stage #1: 1-(2-hydroxyethyl)piperazine; 2,4-dichloro-2-methylpyrimidine With copper(l) iodide; dimethylaminoacetic acid; O4P(3-)*O4P(3-)*3K(1+) In N,N-dimethyl-formamide at 20℃; for 0.666667h;
Stage #2: 2-amino-N-(2-chloro-6-methylphenyl)-1.3-thiazole-5-carboxamide at 120℃; for 6h; Inert atmosphere;
88.41%
1-(2-hydroxyethyl)piperazine
103-76-4

1-(2-hydroxyethyl)piperazine

2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide
1245157-51-0

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

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol for 7h; Solvent; Time; Reflux;87.9%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 5h; Product distribution / selectivity; Reflux;73.6%
2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol
127116-19-2

2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol

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

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
In 1,4-dioxane at 75℃; for 3h; Concentration;83.2%
With potassium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl at 100 - 110℃; for 20h;
C29H30ClN7O3S
1245157-86-1

C29H30ClN7O3S

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: C29H30ClN7O3S With water; sodium hydroxide at 50℃; for 2h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=4;
82.5%
Stage #1: C29H30ClN7O3S With water; sodium hydroxide at 50℃; for 2h;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=4;
82.5%
C29H32ClN7O2S
1245157-70-3

C29H32ClN7O2S

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: C29H32ClN7O2S With boron trichloride In dichloromethane at -15 - 20℃;
Stage #2: With water In dichloromethane Cooling with ice;
82.2%
With boron trichloride In dichloromethane at -15 - 20℃;82.2%
1-(2-hydroxyethyl)piperazine
103-76-4

1-(2-hydroxyethyl)piperazine

(2-(6-chloro-2-methylpyrimidine-4-ylamino)-N-(2-chloro-6-methylpbenyl)thiazole-5-carboxamide)

(2-(6-chloro-2-methylpyrimidine-4-ylamino)-N-(2-chloro-6-methylpbenyl)thiazole-5-carboxamide)

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 65 - 100℃; for 1h; Inert atmosphere;82%
2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid
1245157-42-9

2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid

2-chloro-6-methylaniline
87-63-8

2-chloro-6-methylaniline

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Product distribution / selectivity; Inert atmosphere;80.9%
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Reagent/catalyst; Inert atmosphere;80.9%
C24H30ClN7O2S2
1245157-78-1

C24H30ClN7O2S2

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: C24H30ClN7O2S2 With boron trichloride In dichloromethane at -15 - 20℃;
Stage #2: With water In dichloromethane Cooling with ice;
80.7%
With boron trichloride In dichloromethane at -15 - 20℃;80.7%
C30H34ClN7O3S
1245157-72-5

C30H34ClN7O3S

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: C30H34ClN7O3S With boron trichloride In dichloromethane at -15 - 20℃;
Stage #2: With water In dichloromethane Cooling with ice;
77.3%
With boron trichloride In dichloromethane at -15 - 20℃;77.3%
C26H34ClN7O3S
1245157-77-0

C26H34ClN7O3S

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: C26H34ClN7O3S With boron trichloride In dichloromethane at -15 - 20℃;
Stage #2: With water In dichloromethane Cooling with ice;
72.5%
With boron trichloride In dichloromethane at -15 - 20℃;72.5%
C24H30ClN7O3S
1245157-75-8

C24H30ClN7O3S

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Stage #1: C24H30ClN7O3S With boron trichloride In dichloromethane at -15 - 20℃;
Stage #2: With water In dichloromethane Cooling with ice;
70.6%
With boron trichloride In dichloromethane at -15 - 20℃;70.6%
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

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 16h;36%
methyl 2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formate
1245157-35-0

methyl 2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formate

2-chloro-6-methylaniline
87-63-8

2-chloro-6-methylaniline

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;32%
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Reagent/catalyst; Inert atmosphere;32%
2-chloro-6-methylphenyl isocyanate
40398-01-4

2-chloro-6-methylphenyl isocyanate

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 - -75 °C
1.2: 86 percent / tetrahydrofuran; hexane / 2 h / -78 °C
2.1: NaH / dimethylformamide / 0.5 h
2.2: 95 percent / Bu4NI / dimethylformamide / 16 h / 20 °C
3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
3.2: 83 percent / tetrahydrofuran / 4 h / Heating
4.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C
5.1: i-Pr2NEt / dioxane / 12 h / Heating
View Scheme
Multi-step reaction with 5 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
1.2: 86 percent / tetrahydrofuran; hexane / 2 h / -78 °C
2.1: NaH / dimethylformamide / 0.5 h / 20 °C
2.2: 95 percent / tetrabutylammonium iodide / dimethylformamide / 16 h / 20 °C
3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
3.2: 83 percent / tetrahydrofuran / 4 h / Heating
4.1: 99 percent / TFA; triflic acid / CH2Cl2 / 3 h / 20 °C
5.1: diisopropylethylamine / dioxane / 12 h / Heating
View Scheme
2-chloro-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide
302964-11-0

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

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: NaH / dimethylformamide / 0.5 h
1.2: 95 percent / Bu4NI / dimethylformamide / 16 h / 20 °C
2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
2.2: 83 percent / tetrahydrofuran / 4 h / Heating
3.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C
4.1: i-Pr2NEt / dioxane / 12 h / Heating
View Scheme
Multi-step reaction with 4 steps
1.1: NaH / dimethylformamide / 0.5 h / 20 °C
1.2: 95 percent / tetrabutylammonium iodide / dimethylformamide / 16 h / 20 °C
2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
2.2: 83 percent / tetrahydrofuran / 4 h / Heating
3.1: 99 percent / TFA; triflic acid / CH2Cl2 / 3 h / 20 °C
4.1: diisopropylethylamine / dioxane / 12 h / Heating
View Scheme
N-(4-methoxybenzyl)-2-chloro-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide
834888-63-0

N-(4-methoxybenzyl)-2-chloro-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 83 percent / tetrahydrofuran / 4 h / Heating
2.1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C
3.1: i-Pr2NEt / dioxane / 12 h / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 83 percent / tetrahydrofuran / 4 h / Heating
2.1: 99 percent / TFA; triflic acid / CH2Cl2 / 3 h / 20 °C
3.1: diisopropylethylamine / dioxane / 12 h / Heating
View Scheme
N-(4-methoxybenzyl)-2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide
834888-64-1

N-(4-methoxybenzyl)-2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / CF3CO2H; CF3SO3H / CH2Cl2 / 3 h / 20 °C
2: i-Pr2NEt / dioxane / 12 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 99 percent / TFA; triflic acid / CH2Cl2 / 3 h / 20 °C
2: diisopropylethylamine / dioxane / 12 h / Heating
View Scheme
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide n-butanolate

N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide n-butanolate

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
In ethanol; water at 0 - 80℃; for 5h; Product distribution / selectivity;
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;
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide iso-propanolate

N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide iso-propanolate

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 20 - 100℃;
1-(2-hydroxyethyl)piperazine
103-76-4

1-(2-hydroxyethyl)piperazine

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 8 h / Reflux
2: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane / 2.5 h / 30 °C
2.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / Reflux
2.2: 0.17 h
2.3: 1 h / 10 - 15 °C
3.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 8 h / Reflux
2.1: water; lithium hydroxide / water / 3 h / 50 °C
2.2: 20 °C / pH 6 - 6.5
3.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
2,4-dichloro-2-methylpyrimidine
1780-26-3

2,4-dichloro-2-methylpyrimidine

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloromethane / 2.5 h / 30 °C
2.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / Reflux
2.2: 0.17 h
2.3: 1 h / 10 - 15 °C
3.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: dichloromethane / 2.5 h / 30 °C
2.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / Reflux
2.2: 0.17 h
2.3: 1 h / 10 - 15 °C
3.1: water; lithium hydroxide / water / 3 h / 50 °C
3.2: 20 °C / pH 6 - 6.5
4.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: dichloromethane / 2.5 h / 30 °C
2.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / Reflux
2.2: 0.17 h
2.3: 1 h / 10 - 15 °C
3.1: sodium hydroxide; water / 20 °C
3.2: pH 6 - 6.5
4.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formyl chloride
1245158-43-3

2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formyl chloride

2-chloro-6-methylaniline
87-63-8

2-chloro-6-methylaniline

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 10 - 30℃; Product distribution / selectivity;
Stage #1: 2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formyl chloride; 2-chloro-6-methylaniline In acetonitrile at 10 - 15℃;
Stage #2: With N-ethyl-N,N-diisopropylamine In acetonitrile at 30℃;
13.7 g
2-(6-(4-(2-benzoyloxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid
1245157-82-7

2-(6-(4-(2-benzoyloxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid

2-chloro-6-methylaniline
87-63-8

2-chloro-6-methylaniline

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: sodium hydroxide; water / 2 h / 50 °C
2.2: 20 - 25 °C / pH 4
View Scheme
C22H23ClN6O3S
1245158-47-7

C22H23ClN6O3S

2-chloro-6-methylaniline
87-63-8

2-chloro-6-methylaniline

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
2.1: sodium hydroxide; water / 2 h / 50 °C
2.2: 20 - 25 °C / pH 4
View Scheme
2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol
127116-19-2

2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol

dasatanib
302962-49-8

dasatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / Reflux
1.2: 0.17 h
1.3: 1 h / 10 - 15 °C
2.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / Reflux
1.2: 0.17 h
1.3: 1 h / 10 - 15 °C
2.1: water; lithium hydroxide / water / 3 h / 50 °C
2.2: 20 °C / pH 6 - 6.5
3.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / Reflux
1.2: 0.17 h
1.3: 1 h / 10 - 15 °C
2.1: sodium hydroxide; water / 20 °C
2.2: pH 6 - 6.5
3.1: triethylamine; O-phenyl phosphorodichloridate / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
dasatanib
302962-49-8

dasatanib

dasatinib N-oxide

dasatinib N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In 1-methyl-pyrrolidin-2-one; water at 20℃; for 18h;100%
With hydrogenchloride; dihydrogen peroxide In acetonitrile at 90℃; for 7h; Temperature; Sealed tube;80%
With dihydrogen peroxide In 1-methyl-pyrrolidin-2-one at 40℃;
dasatanib
302962-49-8

dasatanib

N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide dihydrogen bromide

N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide dihydrogen bromide

Conditions
ConditionsYield
With hydrogen bromide In ethanol; water at 70℃;97.7%
4-Ethoxyphenol
622-62-8

4-Ethoxyphenol

dasatanib
302962-49-8

dasatanib

dasatinib 4-ethoxyphenol co-crystal

dasatinib 4-ethoxyphenol co-crystal

Conditions
ConditionsYield
In water at 50℃;97%
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
Conditions
ConditionsYield
In methanol at 25 - 65℃; for 0.833333h; Time;95.6%
methanesulfonic acid
75-75-2

methanesulfonic acid

dasatanib
302962-49-8

dasatanib

N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide dimethanesulfonate salt

N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide dimethanesulfonate salt

Conditions
ConditionsYield
With hydrogen bromide In butanone at 60℃;93.7%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

dasatanib
302962-49-8

dasatanib

2-(6-(4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
881381-50-6

2-(6-(4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Conditions
ConditionsYield
With triethylamine; dmap In N,N-dimethyl-formamide at 20℃; for 1.5h;93.4%
cyclohexylsulfamic acid
100-88-9

cyclohexylsulfamic acid

dasatanib
302962-49-8

dasatanib

N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide monocyclamate salt

N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide monocyclamate salt

Conditions
ConditionsYield
In methanol at 70℃;93.4%
succinic acid anhydride
108-30-5

succinic acid anhydride

dasatanib
302962-49-8

dasatanib

4-(2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl) piperazin-1-yl)ethoxy)-4-oxobutanoic acid

4-(2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl) piperazin-1-yl)ethoxy)-4-oxobutanoic acid

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Schlenk technique;93%
With dmap In N,N-dimethyl-formamide at 50℃; for 18h; Inert atmosphere;90%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;90%
lauric acid
143-07-7

lauric acid

dasatanib
302962-49-8

dasatanib

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazin-1-yl)ethyl dodecanoate

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazin-1-yl)ethyl dodecanoate

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 25h; Inert atmosphere; Cooling with ice;91%
copper(II) nitrate trihydrate

copper(II) nitrate trihydrate

dasatanib
302962-49-8

dasatanib

C22H28ClCuN9O9S*NO3(1-)*H(1+)

C22H28ClCuN9O9S*NO3(1-)*H(1+)

Conditions
ConditionsYield
In methanol; dimethyl sulfoxide at 80℃; for 12h;91%
copper(II) nitrate trihydrate

copper(II) nitrate trihydrate

dasatanib
302962-49-8

dasatanib

C22H28ClCuN9O9S*HNO3

C22H28ClCuN9O9S*HNO3

Conditions
ConditionsYield
In methanol; dimethyl sulfoxide at 80℃; for 12h; Solvent; Temperature;91%
formic acid
64-18-6

formic acid

dasatanib
302962-49-8

dasatanib

C23H26ClN7O3S

C23H26ClN7O3S

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 100℃; for 10h; Temperature;90.4%
1-decanoic acid
334-48-5

1-decanoic acid

dasatanib
302962-49-8

dasatanib

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazin-1-yl)ethyl decanoate

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazin-1-yl)ethyl decanoate

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 25h; Inert atmosphere; Cooling with ice;90.1%
Octanoic acid
124-07-2

Octanoic acid

dasatanib
302962-49-8

dasatanib

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazin-1-yl)ethyl octanoate

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazin-1-yl)ethyl octanoate

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 25h; Inert atmosphere; Cooling with ice;90%
carvacrol
499-75-2

carvacrol

dasatanib
302962-49-8

dasatanib

dasatinib carvacrol co-crystal

dasatinib carvacrol co-crystal

Conditions
ConditionsYield
In methanol at 50℃;90%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

dasatanib
302962-49-8

dasatanib

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazin-1-yl)ethyl tetradecanoate

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)piperazin-1-yl)ethyl tetradecanoate

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 25h; Inert atmosphere; Cooling with ice;88.6%
phthalimide
136918-14-4

phthalimide

dasatanib
302962-49-8

dasatanib

N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-(1,3-dioxoisoindol-2-yl)ethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxamide

N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-(1,3-dioxoisoindol-2-yl)ethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
With diisopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;88%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.166667h;87.8%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

dasatanib
302962-49-8

dasatanib

N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide p-toluenesulfonate salt

N-(2-chloro-6-methylphenyl)-2-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino]-1,3-thiazole-5-carboxamide p-toluenesulfonate salt

Conditions
ConditionsYield
In water; isopropyl alcohol at 70℃; Solvent;87.4%
In ethanol at 65 - 70℃; for 4h;
In ethanol Heating / reflux;
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

dasatanib
302962-49-8

dasatanib

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl palmitate

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl palmitate

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 25h; Inert atmosphere; Cooling with ice;86.5%
stearic acid
57-11-4

stearic acid

dasatanib
302962-49-8

dasatanib

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl stearate

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl stearate

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 25℃; Inert atmosphere; Cooling with ice;86.3%
acetic acid
64-19-7

acetic acid

dasatanib
302962-49-8

dasatanib

N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide
1245157-85-0

N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 25h; Inert atmosphere; Cooling with ice;86%
citric acid triethyl ester
77-93-0

citric acid triethyl ester

dasatanib
302962-49-8

dasatanib

C22H26ClN7O2S*C12H20O7

C22H26ClN7O2S*C12H20O7

Conditions
ConditionsYield
In methanol at 20℃; for 3h;86%
Arachidic acid
506-30-9

Arachidic acid

dasatanib
302962-49-8

dasatanib

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl icosanoate

2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl icosanoate

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 25℃; Inert atmosphere; Cooling with ice;85.3%
dasatanib
302962-49-8

dasatanib

3-bromodasatinib

3-bromodasatinib

Conditions
ConditionsYield
With hydrogen fluoride; antimony pentafluoride; sodium bromide at -20℃;84%

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